The 50 Worst Decisions in the Past 50 Years of American Politics

There’s no silver medal in primary politics. There’s just the winner of the contest and a bunch of losers. This is as basic as it gets, but Donald Trump’s 2024 competitors (with the notable exception of Chris Christie) haven’t seemed to understand this. In 2016, Marco Rubio and Ted Cruz made feeble attempts to take down Trump. This time around, the contenders almost exclusively decided to batter the shit out of one another in a series of brutal primary debates without even once attacking the guy they needed to take down if they wanted to actually win. They were all given endless opportunities to take shots at the former president, but their fear of his base was so intense that they actually defended him over and over about everything from Jan. 6 to the Florida documents case. Ron DeSantis, Nikki Haley, Tim Scott, Vivek Ramaswamy, and all the others not named Christie (who never had any real chance) were basically hoping some outside event would remove Trump from the race and they’d be allowed to have a real primary. During months on the campaign trail, only Haley even tried to take a half-hearted shot at Trump, making tepid comments about his mental fitness before the New Hampshire primary. The primary essentially became a giant collective-action dilemma that will surely result with Trump skating to victory. By letting that happen, the 2024 GOP field will go down in history as a bunch of fools and cowards. 

Barack Obama vacated his Illinois Senate seat when he won the presidency in 2008. The duty to appoint a replacement fell on Illinois Gov. Rod Blagojevich. At the time, Blagojevich was being investigated for fraud by federal authorities, and his phones were tapped. “I’ve got this thing, and it’s fucking golden,” he said during one taped call. “I’m just not giving it up for fucking nothing. It’s a fucking valuable thing, you just don’t give it away for nothing. If I don’t get what I want … I’ll just take the Senate seat myself.” Any new appointee to the Senate seat, he said, would have to pony up a lot of cash. This was unambiguous corruption. Blagojevich was arrested Dec. 9, 2008, and ultimately sentenced to 14 years in jail. His term ended when Donald Trump commuted his sentence in 2020. Trump himself has avoided prison up to this point in his life because he knows you never outright order something illegal when you’re talking to aides. You talk around it. You hint at it. But you never just say it. In other words, Blagojevich is dumber than even Donald Trump. 

Ted Cruz loves to rail against wealthy “elites” that have outsize influence in our political debates, but he’s quite the odd messenger for this sentiment. Cruz attended Princeton University, Harvard Law School, and made a fortune as an attorney. His wife works for Goldman Sachs. They’re worth millions. They are the definition of “elites.” This became painfully clear in February 2022 when Cruz traveled to Cancun with his family while the state of Texas was paralyzed by a winter storm and widespread power outages. They stayed at the Ritz Carlton and chilled on the beach while residents of his state were struggling to find food and not freeze to death in their sleep. Cruz was forced to cut the trip short and travel back, but it was a humiliating episode and evidence of stunningly bad judgment. He’s up for reelection this year. His opponent would be a fool not to work this incident into 2024 attack ads. 

If the Republican Party (or the media) had done even the tiniest bit of research before George Santos won the Republican nomination for New York’s 3rd Congressional District in 2022, they could have spared themselves a lot of embarrassment. As we’ve all learned, Santos was a criminal grifter with a long shocking history of skeevy schemes. He was also a complete fabulist who claimed he worked at Goldman Sachs and Citigroup, attended Horace Mann high school and Baruch College, and had relatives who died in the Holocaust and Sept. 11. None of this was even remotely true. He was also so wildly immoral that he stole $3,000 from the GoFundMe account for the dying dog of a veteran. This is on top of credit-card fraud, identity theft, and many other serious crimes. All of this was hiding in plain sight. It would have just taken the tiniest bit of research to uncover. Nobody bothered.

John Edwards faced an uphill climb when he decided to run for president in 2008. He may have been John Kerry’s Democratic running mate in the previous election, and a gifted retail politician who shined on television, but he was up against Hillary Clinton and Barack Obama for the nomination. He needed every advantage he could get. What he didn’t need was news to emerge in the National Enquirer that he’d impregnated a campaign staffer. He certainly didn’t need the public to find out the affair took place while his wife was battling cancer. This came out before the Iowa caucus, and Edwards was no real risk to Clinton or Obama anyway, but imagine if he’d secured the nomination and the scandal broke before the general election? He would have been ruined. John McCain would have won. It was a profoundly reckless move that forever ended a once-promising political career.

On Oct. 13, 1988, CNN anchor Bernard Show kicked off the second and final presidential debate between Vice President George H.W. Bush and Massachusetts Gov. Michael Dukakis with a shocking question. “Governor,” he began, “if [your wife] Kitty Dukakis were raped and murdered, would you favor an irrevocable death penalty for the killer?” A clever politician would have shown extreme emotion in this moment, and more than a little outrage. They would have said something like, “How dare you even put that image in my head? If such a thing were to happen, I’d hunt the perpetrator down and kill them myself. I can’t believe you’d even ask such a question!” That’s not what Dukakis did. “No, I don’t, Bernard,” he calmly said, like he was talking about the weather and not the hypothetical rape and murder of his wife. “And I think you know that I’ve opposed the death penalty during all of my life.” He droned on and on about the issue of the death penalty, but nobody was really listening. They were just stunned by his calm, expressionless demeanor. The unsettling moment was not the only reason he lost the election the following month, but it definitely didn’t help. 

For six solid days in June 2009, South Carolina governor Mark Sanford went completely off the grid. According to press reports, his staff and even members of his own family were unable to reach him and had no idea where he was. All calls went directly to voicemail. The confusion only grew when a spokesperson for the governor said he was “hiking the Appalachian Trail.” Who would do such a thing totally alone on Father’s Day weekend without alerting your family? It turned out he was nowhere near the Appalachian Trail. He was in Buenos Aires visiting his mistress. Needless to say, this erupted into a giant political scandal that nearly cost him his governorship. It certainly ended his marriage. It did, however, give the world an incredible new euphemism for cheating on your wife: “Hiking the Appalachian Trail.”  

Modern political conventions are tightly scripted affairs where not a single moment is spontaneous. Speakers are given a time slot negotiated down to the second, and they read speeches with every last word approved by the political party. But when Clint Eastwood wanted to address the RNC in 2012 right before Mitt Romney’s acceptance speech, the organizers were so wowed by his star wattage — considering Scott Baio and Stacey Dash are big names in the world of right-wing celebs — that they let him take the stage without a script or any idea what he’d say. The result was a painfully meandering mess during which Eastwood spoke to an empty chair he pretended was Barack Obama. “What do you want me to tell Romney?” Eastwood asked the empty chair. “I can’t tell him to do that to himself.” (In case you missed the subtext, Eastwood is saying that invisible Obama told Romey to fuck himself.) This went on for 12 endless minutes. When it was done, one of Rommey’s advisers actually vomited, knowing it would dominate the news the next day and overshadow Romney’s big speech. It was a total disaster that even Eastwood eventually admitted should never have happened.

Dr. Mehmet Oz was a very successful talk-show host — and a shockingly bad political candidate when he somehow won the Republican nomination for Senate in Pennsylvania in 2022 despite living in New Jersey. In an attempt to win over locals and show he was a man of the people, the good doctor filmed a trip to Redner’s grocery store while on the campaign trail. In a period of about 25 seconds, he committed enough gaffes to destroy his campaign and let John Fetterman beat him even though the Democratic nominee had recently suffered a massive stroke. It started when he referred to the grocery store as “Wegners,” clearly thinking of Wegmans back in New Jersey. He then used the French term “crudités” to refer to a veggie platter, just like your typical blue-collar Pennsylvanian. He capped off the trip by confusing the price-per-pound of every vegetable with the total price, and holding all the items in his hands as opposed to using a cart or basket. He couldn’t have looked more like an out-of-touch, carpetbagging jackass. The grocery store visit crystalized everything that was wrong with his abysmal losing effort.

After Robert Kennedy’s assisination in 1968, it was widely presumed that his brother Teddy Kennedy would eventually pick up the Kennedy torch and run for president himself. Richard Nixon was obsessed with the idea and spent hours grumbling about it in the White House. And were it not for the tragic Chappaquiddick incident in 1969, Teddy would probably have run in 1972. Seven years later, however, when Jimmy Carter was looking weak, he finally went for it. But he clearly didn’t do much media training because he botched the most obvious question imaginable when CBS newsman Roger Mudd asked him why he wanted to be president. The two-minute video of his answer is agonizing to watch since he has absolutely no response that’s even remotely coherent. He just speaks in vague generalities about how other nations are surpassing America, not offering any plan of his own to solve anything. It drew widespread ridicule and helped even a weakened Carter gain the Democratic nomination for a second time. Here’s a good tip: If you want to run for president, come up with a good explanation as to why when someone asks you. You don’t want to look like a fumbling idiot.

Dan Quayle was just 41 years old when George H.W. Bush tapped him as his running mate in 1988. He had been in D.C. for more than a decade, first as a two-term congressman and then as the junior senator from Indiana. Somehow, though, he didn’t radiate political experience and wisdom. Quayle came off to many like an overgrown preppy teen who had no business being one heartbeat away from the presidency. On the campaign trail, he often addressed this concern by pointing out he had just as much political experience as John F. Kennedy had when he entered the White House in 1961. When Quayle repeated this line to Lloyd Bentsen, his opponent in the 1988 vice presidential debate, the Texas senator was ready with a devastating response. “Senator, I served with Jack Kennedy,” Benstsen said. “I knew Jack Kennedy. Jack Kennedy was a friend of mine. Senator, you’re no Jack Kennedy.” It’s one of the greatest debate zingers in history. And even though the Bush-Quayle ticket triumphed just a few weeks later, the attack line lingered. The public never accepted Quayle as a serious contender for the highest office in the land. The presidential campaign he considered embarking on in 1996 never got beyond the exploratory-committee phase. He launched an actual campaign in 2000, but withdrew prior to the first primary. It turned out Bentsen was right. He was no Jack Kennedy. 

Herschel Walker was among the greatest college football players of all time, and fans of University of Georgia Bulldogs will forever see the Heisman winner as a demigod. That doesn’t mean it was a smart move for Republican primary voters from the state to take Donald Trump’s advice in 2022 and nominate Walker for the senate. He had no political experience. He wasn’t a polished speaker. His closet was overflowing with skeletons, including serious allegations of domestic violence. There was even proof that the pro-life candidate once paid for a girlfriend to get an abortion. Many pundits thought a massive “Red Wave” was coming that would wash Walker into the senate anyway, but they were wrong. Raphael Warnock defeated him by 99,389 votes. It was the first time a Democrat won a full term in the U.S. senate since 1986. And had the Republicans nominated even a remotely competent or qualified candidate, it wouldn’t have happened. 

Days after Republican primary voters in Missouri nominated Todd Akin in the 2012 U.S. Senate race, the social conservative went on TV and fielded a question about whether rape victims should be allowed to have abortions. “From what I understand from doctors, that’s really rare,” he said. “If it’s a legitimate rape, the female body has ways to try to shut that whole thing down. But let’s assume that maybe that didn’t work or something. I think there should be some punishment, but the punishment ought to be on the rapist and not attacking the child.” This raised a lot of questions. What doctor told him that the female body has “ways to shut down” a pregnancy if it’s the result of rape? What exactly did he mean by a “legitimate rape”? Did this shut-down process not occur if the rape is illegitimate? It was one of the dumbest statements by a politician in American history, which is really saying something. It also meant the purple state of Missouri went to Democratic candidate Claire McCaskill by a whopping 15 points.

In late 2011, a large group of prominent conservatives that included Henry Kissinger, Nancy Reagan, Bill Kristol, and Rupert Murdoch secretly met with New Jersey Gov. Chris Christie and begged him to run for president. They were horrified that the best GOP options for taking on Barack Obama in 2012 were figures like Newt Gingrich and Rick Santorum. Christie had been the governor of New Jersey for two years at this point, and was already a proven legislator with strong appeal among independents. Had he entered the race, he likely would have cleared the field. But he didn’t run. He wanted to focus on his 2013 reelection campaign, and start focusing on 2016. But when that election came around, the Bridgegate scandal had shattered his reputation. There was also a new guy running for the office named Donald. It wasn’t Christie’s year. It’s certainly not his year in 2024, either. His year was 2012. That was his moment in time. He can never go back there. 

When Joe Biden first ran for president, in the 1988 cycle, he was knocked out of the race in September 1987 — before a single vote was cast — when word surfaced that he used parts of a speech by British politician Neil Kinnock without attribution. The whole thing was an embarrassing debacle, and he didn’t try running again until 20 years later, just as Obama-mania was sweeping the nation. On the very first day of his campaign, he spoke about the freshman senator from Illinois in an interview with The New York Observer. “You got the first mainstream African American who is articulate and bright and clean and a nice-looking guy,” Biden said. “I mean, that’s a storybook, man.” Clean? Articulate? It was a horrible choice of words, and terribly insulting to every previous Black presidential candidate. Biden did his best to fix the mess in the days that followed, but it was hopeless. That “clean, articulate” fellow cleaned his clock in the early primary states. Joe had struck out for a second time. It was hard to imagine he’d ever have the chance to run for president again.

Gerald Ford had a lot to prove when he was sworn in as president after Richard Nixon’s resignation in August 1974. Because he was appointed vice president after Spiro Agnew’s resignation, the Michigan senator is the only president in our history not elected on a national ticket. Many voters looked at him as a foreign-policy novice who lucked into his role. And he didn’t do much to change that perception during a debate with Democratic nominee Jimmy Carter centered around foreign affairs on Oct. 6, 1976. “There is no Soviet domination of Eastern Europe,” Ford said when asked about Soviet influence in Eastern Europe, “and there never will be under a Ford administration.” It was an enormous gaffe that Carter recognized immediately. “I’m sorry,” he said. “Did I understand you to say, sir, that the Soviets are not using Eastern Europe as their own sphere of influence in occupying most of the countries there?” There’s been much debate over the years about exactly how much Ford suffered as a result of his statement, which was simply untrue no matter how you looked at the map, but Carter’s numbers surged right after the debate. “”If it hadn’t been for the debates, I would have lost,” Carter said years later. “They established me as competent on foreign and domestic affairs and gave the viewers reason to think that Jimmy Carter had something to offer.”

History has been very unkind to Jimmy Carter’s 1979’s “malaise” speech, in which he told Americans there was a “crisis of confidence” cutting away at our strength as a nation. “It is a crisis that strikes at the very heart and soul and spirit of our national will,” he said. “We can see this crisis in the growing doubt about the meaning of our own lives and in the loss of a unity of purpose for our nation.” He went on to call for a cap on oil imports, which he hoped to replace with solar power and an expanded domestic energy sector. The response was initially quite positive, but he followed it up two days later by firing much of his cabinet, creating the perception that his presidency was in a state of crisis. “I think that’s where the elites turned definitively against Carter,” said Carter speech writer Hendrik Hertzberg, “and that trickled down before too long to everybody else.”

When George H.W. Bush accepted the Republican nomination for president in 1988, he made a promise that dominated the headlines for days. “Congress will push me to raise taxes, and I’ll say no,” he said. “And they’ll push, and I’ll say no, and they’ll push again, and I’ll say to them, ‘Read my lips: no new taxes.’” This made a lot of sense when trying to shore up the Republican base. It was much harder to keep the promise once he actually won and had to negotiate with a legislature controlled by Democrats. Just two years later, he was forced to raise taxes as part of a deal with Democrats. It was a smart move in terms of governing America, but it was a horrible move politically. He handed the Democrats an incredible gift they used very effectively in the final weeks of the campaign. An image of Bush making the infamous pledge ran over and over in commercials for Bill Clinton. It was a good lesson for all future politicians: Don’t make promises you won’t be able to keep.

The road to the White House goes directly through the Midwest. If you can’t win Michigan, Pennsylvania, and Wisconsin, it’s very hard to become president. (Ohio was on this list until very recently, but it’s gone dark-red in the Trump era). Barack Obama should have kept this in mind when he spoke at a closed-door fundraiser to deep-pocketed San Francisco donors in 2008. “You go into these small towns in Pennsylvania and, like a lot of small towns in the Midwest, the jobs have been gone now for 25 years and nothing’s replaced them,” he said. “And they fell through the Clinton administration, and the Bush administration, and each successive administration has said that somehow these communities are gonna regenerate, and they have not. And it’s not surprising then they get bitter, they cling to guns or religion or antipathy toward people who aren’t like them, or anti-immigrant sentiment or anti-trade sentiment as a way to explain their frustrations.” To be very clear, we’re not saying this analysis was totally wrong. It was just really dumb to say out loud, especially to a room full of rich people in San Francisco, when you’re trying to win voters in the Midwest skeptical of a guy named Barack Hussein Obama. The line about “clinging to religion” was especially dunderheaded. Obama learned the vital lesson here that whenever you are speaking to a room with more than zero people in it, you’re potentially speaking on the record. And if Mitt Romney had been paying attention, the whole 47 percent thing would never have happened. 

Al Gore had plenty of reasons to resent Bill Clinton by 2000. He’d spent eight years in his shadow, and the last few were spent mired in the Monica Lewinsky scandal. It was a huge distraction that overshadowed everything they accomplished together during Gore’s time as vice president. He was ready to stand on his own and leave Clinton in the past, which is why he insisted the president stay off the campaign trail in 2000. The only problem is that Clinton was incredibly popular in 2000. Most Americans felt the impeachment trial that developed out of the Lewinsky scandal was an enormous overreach by the Republicans. Clinton could have drawn huge crowds all across the country and rallied support for Gore. If he helped Gore pick up a mere 538 votes in Florida, it would have been enough to push him over the edge. There are countless “what ifs” surrounding the 2000 election, and this one is a biggie. 

Joe Biden chaired the Senate Judicial Committee when George H.W. Bush nominated Clarence Thomas to fill the Supreme Court seat vacated by Thurgood Marshall. And when Anita Hill, who had worked with Thomas in the Department of Education, stepped forward to accuse him of sexual harassment, Biden oversaw the proceedings. It was a chance for Biden to show the world he deserved another shot at the presidency after totally blowing things back in 1988. But he not only sat back while Republican senators took shot after shot at Hill, making little attempt to rein them in, but he also refused to call witnesses that might corroborate Hill’s testimony. The hearings turned into Thomas’ word against Hill’s. Biden wound up voting against Thomas’ confirmation, but the damage to his reputation was done. He tried to smooth things over in a private phone call to Hill after announcing his 2020 presidential campaign, but it didn’t really work. “The focus on apology to me is one thing,” she told The New York Times. “But he needs to give an apology to the other women and to the American public because we now know how deeply disappointed Americans around the country were about what they saw.”

Prior to Rick Perry’s entrance into the 2012 Republican primary race, most pundits felt he had a very strong chance of securing the nomination. He was a popular governor of Texas with a George W. Bush-like swagger that played well with Republican voters. He was also up against a pathetic group of has-beens and nutjobs like Newt Gingrich, Rick Santorum, Michele Bachmann, and Ron Paul. Mitt Romney was the only other candidate in the race who seemed like he had a serious chance of victory. All of that changed on Nov. 9, 2011, during a debate in Auburn Hills, Michigan. “It’s three agencies of government when I get there that are gone,” Perry said. “Commerce, Education, and the…what’s the third one there?” Ron Paul suggested that he was maybe trying to think of the EPA. “EPA!” Perry said. “There you go.” The moderator asked him if the EPA was indeed the third agency he’d eliminate. “No sir,” said Perry. “The third agency of government I would do away with … the, um … education, commerce, and let’s see … I can’t. The third one, I can’t. Oops.” And just like that, Perry no longer seemed like a political dynamo. He seemed like a seventh-grader trying to bullshit his way through a class presentation he didn’t prepare for. It effectively marked the end of his campaign, and the real moment that Romney secured the nomination, despite brief surges in the months ahead for Gingrich and Santorum. But it wasn’t the end of Perry’s political career. Once Donald Trump took office, he appointed Perry to be the head of the Department of Energy. By that point, Perry no longer felt it should be eliminated. 

In politics, timing is everything, and few politicians have learned that lesson as brutally as Jeb Bush did in 2016. When he was elected governor of Florida in 1998, the second son of George H.W. Bush seemed poised to one day take the White House. He just had to wait for his older brother George W. to serve out his two terms. But by 2008, the country had enough of the Bush family. He’d have to wait a little longer. Taking on Obama in 2012 would have been suicidal, but by 2016, it was now or never. The entire GOP apparatus got behind him, and money began pouring in by the tens of millions. This was his moment to be the chosen one. The only problem was that a narcissistic real estate developer from New York wanted to be president, too. And he took particular delight in viciously mocking Jeb on the campaign trail, somehow turning “low energy” into a stinging insult. Before long, a dejected Jeb was forced to tell a tiny crowd “Please clap” during a lackluster campaign event. In the end, Jeb raised $130 million and had little to show for it besides months and months of ritualistic humiliation. What initially seemed like a coronation had transformed into the cringiest comedy in recent political memory. 

Many political figures have been removed from office and prosecuted over the years due to sexual harassment, sexual assaults, or old-fashioned graft. In nearly every case, authorities had to build airtight cases against the figures based on the testimony of other people. After all, it’s not like anyone would be dumb enough to maintain detailed diaries chronicling their own crimes. Let’s rephrase that. Nobody besides former Oregon Sen. Robert Packwood would be dumb enough to keep such diaries. When allegations surfaced in a 1992 Washington Post story that Packwood had a long history of assaulting female staffers, the world learned that he’d maintained a diary for decades. The books contained names of women he’d assaulted, details of the incidents, and even confessions that he’d accepted money in exchange for political favors. It was a gift to investigators, and it forced him to resign in disgrace. 

It may be hard for anyone under the age of 30 to believe, but Rudy Giuliani was once a beloved political figure that unified both sides of the political spectrum for his leadership as mayor of New York after 9/11. Time magazine named him Person of the Year in 2001, and everyone from Oprah Winfrey to David Letterman sang his praises. It was widely presumed that he’d be elected president one day. When word first surfaced that he was thinking about running in 2008, he became an early front-runner. But Rudy’s enemies knew a precious secret about him that would eventually be his undoing: He’s crazier than a shithouse rat. This didn’t become evident to the broader public until Donald Trump entered the political arena in 2015, and Rudy became one of his most eager lapdogs. When Trump lost the 2020 election, Giuliani was the loudest voice in his ear telling him to shred the Constitution and do whatever he could to retain his grip on power. We all remember the Four Seasons Total Landscaping press conference, the hair dye running down his face, the Borat 2 interview, and countless other media appearances in which he seemed ready for a straitjacket. It all culminated in a lawsuit by two Georgia election workers he falsely accused of manipulating vote totals. A jury came back with a $148 million judgment, forcing him to declare bankruptcy. All of this would have been avoided had Rudy merely stayed far from Trump’s orbit and kept his craziness hidden deep inside. 

The 2020 election took place before the first Covid vaccines were available to the public. That’s why states across the country took unprecedented steps to expand mail-in voting and the use of drop boxes. This was an opportunity for both parties to pad their margins prior to election day, but Trump refused to take advantage of it. He told his supporters that mail-in ballots were somehow tainted and they should only vote on Election Day in person. “[Ballots are] being sold and dumped in rivers,” he said without a shred of evidence. “This is a horrible thing for the country.” As anyone could have guessed, Biden cleaned up when it came to (100 percent legal and legitimate) ballots cast prior to Election Day. There was a decent chance Trump could have won if his own bullshit conspiracy theories hadn’t clouded his thinking. 

Take a good look at the image of the ballot above. Notice that Al Gore and Joe Lieberman are listed second. You see that second hole right next to the word “Democrat?” At first glance, that certainly looks like what you punch to vote for Gore/Liberman, right? This is the situation that many elderly Palm Beach County residents faced in 2000 when they went to vote for president. This “butterfly ballot” is so confusing that it’s in complete violation of Florida election law. And a large number of people either mistakenly voted for Pat Buchanan or punched both the second and third holes, destroying their ballots. George Bush wound up winning Florida by a mere 537 votes. There were 19,000 ballots in Palm Beach Country destroyed by overvotes. Every nonpartisan study after the election concluded that Al Gore would have won the state had Palm Beach County simply placed all the candidates for president in a single column. This was the ultimate “Butterfly Effect.” 

As the governor of New York and the state’s former attorney general, Eliot Spitzer should have known what happens when you arrange for an escort to cross state lines for a liaison, and then pay for her services with a wire transfer. It leaves a paper trial and bumps the offense up to a federal crime. But back in 2008, Spitzer obviously wasn’t thinking too clearly. He’d come across the Emperor’s Club VIP escort-service website and was sending them thousands of dollars for intimate encounters with strangers. At one point, he arranged for 22-year-old Ashley Dupré to travel from New York for a meetup in a D.C. hotel. Once the world learned of this, Spitzer was in deep trouble with the law. It was also the end of his political career. 

It’s difficult to think of a more dramatic moment in the recent history of the United States Senate than July 28, 2017. Republicans had spent the past seven years desperately trying to repeal the Affordable Care Act, Barack Obama’s signature domestic policy achievement as president, and the moment to do it was finally right in front of them. The House had already voted to strike down the law. Donald Trump was president. Republicans controlled the Senate. The only problem was that moderate Republican Sens. Susan Collins and Lisa Murkowski were on record as votes against the bill. It was all going to come down to John McCain. The Arizona senator opposed the law, and since Barack Obama denied him the presidency back in 2008, this was a chance to enact sweet revenge. But Trump had mercilessly attacked McCain over the past couple of years, even mocking his service in the Vietnam War. McCain was also undergoing treatment for an aggressive form of brain cancer. He knew the odds were very low he’d be able to beat it. In other words, he was out of fucks to give. On that fateful night, he walked into the Senate Chamber, listened to the desperate pleas of his Republican colleagues begging him to support the repeal bill, and then gave a thumbs down when his name was called. Obamacare lived. Millions of people kept their health insurance. It was a huge blow to Trump. It might have all gone very differently if Trump had only shown proper respect to a beloved war hero and not belittled him out of petty jealousy. Once again, he could have gotten his way if only he hadn’t acted like a dumb bully.

This is a tricky one. Gerald Ford’s decision to pardon Richard Nixon of all crimes related to Watergate within the first month of his presidency had a lot of positive repercussions for the country. As Ford himself put it, the pardon ended our “long national nightmare” of Watergate and allowed America to finally start looking ahead. If Nixon had been put on trial, it would have hopelessly divided Americans and been an absolute circus. It’s easy to argue that losing the presidency was a pretty fitting punishment for Watergate. Throwing Nixon into a prison cell on top of that wouldn’t have accomplished much. On the other hand, the pardon caused Ford’s popularity to plummet. Conspiracy theorists felt it was a part of a secret deal that Nixon made with Ford when he appointed him vice president. That’s never been proved and almost certainly isn’t true, but the whole thing was a political nightmare for Ford and became the defining moment of his brief, accidental presidency. It may have been a brave move that benefited America, but it was a dumb political move for Ford. 

In 1948, South Carolina Gov. Strom Thurmond was so infuriated with President Harry Truman’s stance on civil rights, particularly his decision to desegregate the armed forces, that he left the Democratic party and ran for president on the pro-segregation Dixiecrat ticket. Fifty-four years later, at Thurmond’s 100th-birthday party, Senate Minority Leader Trent Lott shared some thoughts with the event’s attendees. “’When Strom Thurmond ran for president, we voted for him,” he said. “We’re proud of it. And if the rest of the country had followed our lead, we wouldn’t have had all these problems over the years, either.” To give Lott the benefit of every doubt, he was possibly just trying to flatter an extremely old and feeble man. But he explicitly said America would be better off had a segregationist been elected president in 1948. He also suggested the Civil Rights Movement created unspecified “problems” we could have avoided had the South’s Jim Crow system stayed in place. Lott did everything he could to defend himself in the days that followed, but it was no use. He was forced to resign his leadership role in disgrace. 

For a brief moment in early 2020, Joe Biden looked like he was in real trouble in the Democratic primary. After leading in the polls for a year, he came in fourth in the Iowa caucus, and fifth in the New Hampshire primary. Bernie Sanders, meanwhile, was ascendent. This caused a complete freakout in the mainstream wing of the party since many felt that the self-described “socialist” was likely to get creamed by Trump in the general. This is when former New York Mayor Mike Bloomberg entered the story, thinking it was his duty to save America. In a period of just two months, Bloomberg somehow spent a billion dollars of his own fortune on a last-minute campaign. But just two minutes into his first debate, Elizabeth Warren threw him into a buzzsaw. “I’d like to talk about who we’re running against – a billionaire who calls women ‘fat broads’ and ‘horse-faced lesbians,’” she said. “And, no, I’m not talking about Donald Trump. I’m talking about Mayor Bloomberg.” By the time she was done, his campaign was a smoldering ruin. He wound up only winning delegates in American Samoa. In the history of politics, nobody has ever spent so much and achieved so little.

Ronald Reagan had always had a unique ability to avoid political scandals. Something about his sunny optimism and grandfatherly persona just made many Americans trust him. But his good luck ran out when the Iran Contra arms-for-hostages story broke during his second term. Reagan had spent months denying he knew anything about his administration’s elaborate secret plan to sell weapons to Iran in exchange for the release of American hostages in Lebanon, and then funnel the money to U.S.-backed right-wing insurgents in Nicaragua. But as the facts piled up, the Gipper’s story seemed less and less believable. Things came to a head March 17, 1987, when Reagan addressed the situation in a nationwide Oval Office speech. “A few months ago I told the American people I did not trade arms for hostages,” he said. “My heart and my best intentions still tell me that’s true, but the facts and the evidence tell me it is not.” The American people didn’t care what ridiculous, self-serving lies his heart and “best intentions” told him. They cared about what actually happened. They cared that he lied to them. The fiasco caused his approval rating to dramatically slip. The whole “my lying heart is to blame” excuse didn’t fly. 

When New York Rep. Anthony Weiner accidently posted a photo of his “man bulge” on Twitter on May 27, 2011, we all had a good laugh. Despite his initial claim that he’d been hacked, it was clear he meant to send the photo privately to a woman and had made a terrible mistake. We kept laughing weeks later when more photos emerged and he admitted to sexting with random young women he’d met online. Once a fully nude photo emerged and President Obama joined many other Democrats in calling for his resignation, we stopped laughing. The once promising political figure not only destroyed his career, but he’d placed his wife — Hillary Clinton aide Huma Abedin — into a nightmarish situation. Things didn’t grow really dark, however, until 2015, when reports surfaced that Weiner was sending nude photos to a 15-year-old girl. This was the final straw for Abedin, who finally filed for divorce. It was also the final straw for our legal system. He spent 15 months at the Federal Medical Center in Devens, Massachusetts. In the midst of all this, emails supposedly at the center of the FBI’s Hillary Clinton email investigation were found on his laptop.

Just 11 days before Americans headed to the polls in 2016, James Comey dropped one of the biggest October surprises in American history. “The FBI has learned of the existence of emails that appear to be pertinent to the investigation,” he wrote to a group of senators. “The FBI should take appropriate investigative steps designed to allow investigators to review these emails to determine whether they contain classified information, as well as to assess their importance to our investigation.” In other words, the investigation into Hillary Clinton’s emails — a media-feeding frenzy that found nothing warranting a criminal  prosecution–was back on thanks to Anthony Weiner’s laptop. This was a shameful dereliction of the FBI’s duty to avoid inserting itself into political matters right before an election. Comey eventually admitted this was a “serious error of judgment,” but by then it was way too late. Clinton spent the final days of the 2020 campaign under the cloud of a reopened investigation that (once again) ultimately went nowhere. Swing voters turned on her. According to many analysts, it played a huge role in handing Trump the White House. 

A major natural disaster can offer an opportunity for a president to showcase leadership, competence, and empathy — or to hemorrhage support if they botch the aftermath. George W. Bush learned that lesson in 2005 when he posted a photo of himself looking down at the devastation of Hurricane Katrina from the safety of Air Force One. The image went viral and made him look hopelessly out of touch. “I was the one who should have said: ‘(A) Don’t take my picture; (B) let’s land in Baton Rouge; (C) let’s don’t even come close to the area,’” Bush said in 2010. “The next place to be seen,” he said, “is in Washington at a command center. I mean it was my fault.” Once he did finally touch down on the ground, several days later, he turned to FEMA Director Michael Brown and uttered an immortal phrase, “Brownie, you’re doing a heck of a job.” Not a single other person in the state of Louisiana agreed with this assessment. Bush’s approval numbers went into a free fall. Thanks to his mishandling of Katrina and other public-relations calamities, like his ill-fated attempt to privatize social security, the Terri Schiavo controversy, and the Scooter Libby scandal, Bush spent 2005 and 2006 in one of longest losing streaks in presidential history and wound up losing both houses of Congress in the 2006 midterms. 

The Supreme Court is ostensibly an apolitical body. But as we all know, that’s complete bullshit in practice. The nine justices follow our national debate as close as any political pundit, and it shapes their jurisprudence in countless ways. It’s even true when it comes to the timing of their retirements. Conservative judges want Republican presidents to name their replacements. Liberal judges want Democratic presidents to name their replacements. Ruth Bader Ginsburg had a golden opportunity to do just that once Barack Obama took office in 2009 and Democrats controlled the Senate. She was 76 at the time, had already survived colon cancer, and was in the midst of battling pancreatic cancer. But she was a tough cookie and she refused to step down. This became a huge problem once Donald Trump took office in 2017 and her health declined further. She managed to somehow stick it out until Sept. 18, 2020. The presidential election was less than two months away. But there was plenty of time for Trump to name a successor after RBG passed and ram it through the Republican-controlled Senate, which is exactly what he did. This completely shifted the makeup of the court and paved the way for the repeal of Roe v. Wade. As the Supreme Court has lurched rightward, Ginsburg’s hubris has severely cut into her status as a liberal hero.

When running for president, it’s imperative to present yourself in a strong, dignified manner so voters can imagine you as a future commander in chief. You don’t want to give your opponents any sort of image they can use to make you look weak or unserious. That’s why President Obama refused to even put a football helmet on his head in 2013 when the Naval Academy football team visited the White House. “Here’s the general rule: You don’t put stuff on your head if you’re president,” Obama said. “That’s Politics 101. You never look good wearing something on your head.” Michael Dukakis didn’t take that class before running for president in 1988 — not only did he put a helmet on, but he also rode around in a tank in front of reporters. He was attempting to project strength and familiarity with the military at a time when the Cold War was still raging. But his name was written across his helmet like he was a preschooler. He looked like a small child playing war games on the playground. It was a gift from the heavens to the Bush campaign. They used it in a series of devastating attack ads that helped sink the Dukakis campaign.

On May 1st, 2003 — just six weeks after the start of the war in Iraq — President George W. Bush landed on the U.S.S. Abraham Lincoln aircraft carrier off the coast of San Diego. With cameras rolling and a crowd of cheering soldiers on board, he walked out of a Lockheed S-3 Viking airplane in a flight suit. A giant banner on the ship read “Mission Accomplished.” “Major combat operations in Iraq have ended,” he said. “In the battle of Iraq, the United States and our allies have prevailed.” But the mission wasn’t accomplished. The war was far from over. This was an insanely premature victory lap. And as the months ticked by and U.S. soldiers continued dying on the ground, it looked more and more ridiculous.

John McCain knew he needed to make a big move in the summer of 2008. Barack Obama was firing up liberals who were desperate to take back the White House after eight years of George W. Bush. McCain’s initial impulse was to send shockwaves through the system by picking Joe Lieberman as his running mate. They were longtime best friends, and McCain thought he could sell it since Lieberman had left the Democratic Party two years earlier. But Lieberman was still pro-choice, and he was still Al Gore’s former running mate. This simply wasn’t going to fly with the Republican Party. It would have led to a nasty floor battle at the convention. Without much time on the clock, McCain decided instead to select Alaska governor Sarah Palin despite knowing little about her or her background. As we all remember, this didn’t work out well for him in the long run. Palin simply wasn’t ready for the spotlight, and it became a huge distraction for McCain in the final weeks of his doomed campaign. 

There’s no way of looking back on Bill Clinton’s behavior toward Monica Lewinsky and feel anything but disgust. He was the leader of the free world. She was a 21-year-old White House intern. The power dynamic was tilted to an insane degree. It will forever tarnish his legacy. But once the truth of their relationship surfaced, he should have admitted to it and attempted to move on with the business of running the country. He instead decided to look into television cameras and lie his ass off. “I want to say one thing to the American people,” he said. “I want you to listen to me. I’m going to say this again: I did not have sexual relations with that woman, Miss Lewinsky. I never told anybody to lie, not a single time, never. These allegations are false.” This did nothing but dig him an even deeper hole.

Bill Clinton didn’t just lie to the American people about his relationship with Monica Lewinsky. He also lied about it while under oath in a deposition related to the Paula Jones lawsuit. This gave the House of Representatives enough ammo to impeach him since that’s technically a crime, but the action ultimately boomeranged against them. As month after month ticked by and the Republicans simply couldn’t move on, the country started to rally behind Clinton. His approval rating began spiking upward. News came out that Speaker of the House Newt Gingrich had had an affair of his own. The Republicans lost seats in the 1998 midterms. Gingrich resigned from Congress in 1999. Clinton left office in 2001 with a 65-percent approval rating, which was higher than any departing president since Harry Truman in 1953. This would have all played out very differently had the Republicans not overplayed their hand by impeaching the president for lying under oath about an affair, but they simply couldn’t help themselves.

Die-hard supporters of Donald Trump believe that there’s always a method to his madness. They think that no matter what dumb thing he says or does at any given moment, it’s all part of some game of 4D chess only he can see. That was pretty tough to argue in April 2020 when Trump shared a passing thought with the world during a Covid briefing about the effectiveness of washing surfaces with bleach to kill the virus. “Supposing we hit the body with a tremendous — whether it’s ultraviolet or just very powerful light — and I think you said that that hasn’t been checked, but you’re going to test it,” he said. “And then I said, supposing you brought the light inside the body, which you can do either through the skin or in some other way, and I think you said you’re going to test that, too. It sounds interesting. And then I see the disinfectant, where it knocks it out in a minute. One minute. And is there a way we can do something like that, by injection inside or almost a cleaning. Because you see it gets in the lungs, and it does a tremendous number on the lungs. So it would be interesting to check that.” To summarize: The sitting president of the United States was telling the country that ingesting bleach might kill the virus. This wasn’t 4D chess. This wasn’t part of a master plan. It was yet more evidence that Trump is a complete moron.

From the very beginning of Gary Hart’s presidential campaign in 1987, rumors swirled that the Colorado senator was engaging in an extramarital affair. “Follow me around,” a frustrated Hart told the press in May 1987. “I don’t care. I’m serious. If anybody wants to put a tail on me, go ahead. They’ll be very bored.” This wasn’t smart. Reporters from the Miami Herald took up the challenge and started following him around. They saw campaign aide and model-actress Donna Rice enter his house and apparently spend the night. Hart and Rice both denied that anything happened, but the press was in a feeding frenzy at this point. He suspended his campaign days later. The following month, photos emerged of Rice and Hart together on a yacht called Monkey Business. We’ll never know what exact sort of monkey business took place between Hart and Rice, but in politics, perception is reality, and the perception of Hart as a two-timing liar sunk his candidacy. 

In May 2012, just as a bruising primary for the Republican nomination was winding up, Mitt Romey spoke at an off-the-record, closed-door campaign event in Florida for wealthy donors. During a Q&A, Romney was asked how he planned to defeat Barack Obama in the general election. “There are 47 percent of the people who will vote for the president no matter what,” he said. “They are dependent upon government, who believe that they are victims, who believe the government has a responsibility to care for them, who believe that they are entitled to health care, to food, to housing, to you-name-it.… [M]y job is not to worry about those people. I’ll never convince them they should take personal responsibility and care for their lives.” Little did he know that a bartender was secretly recording him or that the progressive magazine Mother Jones would wind up with video of the event thanks to work by Jimmy Carter’s grandson, James Carter IV. The Obama campaign wanted to paint Romney as a wealthy plutocrat with little regard for regular Americans, so the leaked video was a gift from the heavens. There are many reasons that Romney lost in 2012, but this supreme gaffe definitely played a role. It’s also a very good political lesson: There’s no such thing as a truly private speech or even a private moment on the campaign trail. Presume cameras are running at all times. And if you can, don’t say that nearly half of Americans are freeloading bums. They don’t like that.

About a week before the 2016 election, the Associated Press ran an article about Hillary Clinton’s odd decision to not visit Wisconsin a single time during the general-election campaign. “This ends a streak of at least 10 presidential elections in which both the Democratic and Republican candidates made appearances in Wisconsin,” read the report. “Clinton is clearly in the lead in Wisconsin, running about seven percentage points ahead in the polls.” But the 2016 polls drastically undercounted white working-class support for Donald Trump. And when election night came, Clinton lost the state by 22,748 votes. If she’d only poured resources into Midwest states like Wisconsin and Michigan, she might have pulled out a win.

In the 2000 election, 97,488 Floridians went to the polls and voted for Ralph Nader over Al Gore or George W. Bush. The vast majority of them were disaffected liberals who saw little difference between the two candidates and voted for Nader as a means to protest the two-party system. A handful of them possibly thought that Nader had a legit chance of becoming president, but they were fooling themselves. These were symbolic votes. The only problem is that in an election that close — as all the polls predicted it would be — every single vote mattered, even the symbolic ones. If a mere 538 out of those 97,488 people voted for Gore, he would have won. The entire 21st century would have unfolded in a radically different way. The Iraq War may never have happened, and it’s very likely Donald Trump would never have been elected president. Most dumb decisions on this list were made by politicians, but this one is on the voters – and in this case voters who prided themselves on how smart and righteous they were. Those 97,488 people made a very dumb decision. We’ve been paying for it ever since.

Mitch McConnell and Donald Trump make no effort to hide the fact that they absolutely despise each other. Trump sees the Senate Minority Leader as a wimpy, establishment tool who was never allied with the MAGA right during his presidency. McConnell, meanwhile, sees Trump as an undisciplined buffoon who squandered opportunity after opportunity to muscle conservative bills through congress during a period when Republicans controlled both houses. The Republicans lost the Senate on Jan. 5, 2021, because Trump told Georgia voters it was fruitless to vote in the state’s “rigged” runoff elections. He basically tried to overthrow the U.S. government the following day. On that infamous night, McConnell gave a powerful address where he defended the integrity of the 2020 election and decried efforts by some Republican members of Congress to block its certification. “We’ll either hasten down a poisonous path where only the winners of election actually accept the results,” he said, “or show we can still muster the patriotic courage that our forebears showed not only in victory, but in defeat.” But when the House impeached Trump a few weeks later and the Senate had the chance to convict him, barring the disgraced ex-president from holding elected office again, McConnell lost his courage. He didn’t whip any votes against Trump, and he didn’t even vote for conviction himself. “We have a criminal-justice system in this country,” he said. “We have civil litigation. And former presidents are not immune from being held accountable by either one.” He didn’t understand that efforts to hold Trump accountable via the courts would only increase his popularity with the deranged Republican base. McConnell didn’t understand that Trump’s supporters wouldn’t turn on him even if he was convicted of a felony, and that Trump would simply pardon himself if he won. The one chance to stop Trump in 2024 was in the Senate in 2021. McConnell didn’t want to take the political heat for doing it. If he could go back now, he’d probably make a different choice.

For the past few decades, the White House Correspondents’ dinner has been a chance for presidents to put politics aside and try their hand at stand-up comedy. The room is often packed with celebrities, which naturally leads to some gentle roasting. In 2011, The Washington Post invited Donald Trump to attend the event, and then-president Obama couldn’t resist zinging the world’s foremost birther, comparing his absurd racist theories on the legitimacy of the president’s birth certificate to moon-landing deniers and UFO obsessives. He closed by mocking Trump’s reality show The Celebrity Apprentice. “The men’s cooking team did not impress the judges from Omaha Steaks,” Obama said. “And there was a lot of blame to go around. But you, Mr. Trump, recognized that the real problem was a lack of leadership. And so ultimately, you didn’t blame Lil Jon or Meatloaf. You fired Gary Busey. And these are the kind of decisions that would keep me up at night. Well handled, sir. Well handled.” Trump tried to laugh off the remarks, but he was fuming on the inside. “I think that is the night he resolved to run for president,” Trump toady Roger Stone said years later. “I think that he is kind of motivated by it: ‘Maybe I’ll just run. Maybe I’ll show them all.’” Nobody could have anticipated how the dominos would fall after that night, but if Obama could go back in time, he probably wouldn’t have humiliated Trump in public like that.

Almost everyone who visited Richard Nixon in the Oval Office between February 1971 and July 1973 had no clue that their every word was being picked up by tiny, hidden microphones, and recorded on a series of Sony TC-800B machines running in a back room. The system was put in place by the president so he’d have 100-percent accurate records of everything that happened during his time in office. Nixon assumed he’d use the flattering parts for his memoirs and private archive, and no one would ever hear the rest. That’s why he was so comfortable using foul language, making shockingly racist and misogynistic comments, and plotting illegal ways to get the White House out of the Watergate mess. That last part became a big issue in the summer of 1973 when White House aide Alexander Butterfield told Congress about the taping system, and a bigger issue in July 1974 when the Supreme Court ordered Nixon to release the Watergate tapes. If the tapes didn’t exist, he could have kept on declaring his innocence and possibly saved his presidency. But the White House tapes destroyed any chance of that. He had only himself to blame. If you’re going to commit crimes, don’t painstakingly document yourself doing them.