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The 33 worst days of Trump’s political career, ranked

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Tuesday was a bad day for Donald Trump.

The former president invested heavily in the election of his old friend Herschel Walker to the Senate from Georgia. That Walker failed to win outright in November was one of many ways in which the limits of Trump’s political power were shown by the 2022 midterms, but at least Trump might see redemption if Walker prevailed in the runoff.

He didn’t. And not only did Walker not win, but his loss came only hours after Trump’s private business was found to have committed tax fraud — a rare loss for the Trump Organization in its long-standing battles against enforcement authorities.

Again: It was a bad day. But it seems useful to consider how bad it was, relative to the various other bad days Trump has seen since he decided to run for president back in 2015. There have been a lot of bad days. So, how bad was this one?

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This is a subjective thing to assess, certainly, with unclear boundaries. What do we mean by “bad,” for example? Bad for whom? How?

Our subjective answer was to focus on days that helped define how Trump has come to be understood as a politician, days that reinforced or established negative characteristics that will continue to linger around the 2024 candidate. Days that helped cement Republican skepticism or that bolstered voter concerns about his leadership.

It’s possible, given that Trump’s political career now stretches back more than seven years, that we’ve forgotten some egregious examples. But we did pick out 33 particular days — including Tuesday — that seemed like they might be ones that stand out as exceptionally bad for the former president.

They are presented below, from least to most bad for Trump.

33. Dec. 18, 2018: Trump Foundation forced to close. Questions about Trump’s use of his personal nonprofit had lingered for months, thanks largely to reporting from The Washington Post. It came to a head in the second year of his presidency, when he agreed to shutter the entity following revelations that it was used to aid his 2016 election.

32. July 31, 2017: Anthony Scaramucci fired. The firing of Scaramucci as White House communications director after only 11 days did not alter the trajectory of the administration. But it was representative of the tumult that plagued Trump’s tenure — and of his approach to staffing decisions.

31. May 10, 2017: Reveals classified info to Russian officials. During an unusual meeting in the Oval Office with senior Russian officials — a questionable decision in its own right — Trump revealed secret information obtained from Israel. The meeting came the day after he fired FBI Director James B. Comey, an act that he told the Russians would ease the pressure he faced.

30. Oct. 30, 2017: Paul Manafort indicted; court blocks military transgender ban. Trump’s 2016 campaign manager, Paul Manafort, and his top deputy were indicted as part of the Russia investigation. Ultimately, it would be revealed that Manafort had passed campaign polling data to a colleague linked to Russian intelligence. On the same day, a court blocked Trump’s effort to ban trans service members.

29. Jan. 30, 2017: Travel ban fight; acting attorney general fired. Soon after taking office, Trump enacted a ban on immigration from several heavily Muslim countries, triggering protests. The acting attorney general, Sally Q. Yates, refused to defend the policy and was fired.

28. Jan. 25, 2019: Capitulates on government shutdown. In late 2018, under pressure from right-wing commentators, Trump declined to sign a government funding bill in an attempt to force Congress to approve funding for a border wall. Congress declined. Without funding, the government shut down — until Trump finally capitulated.

27. Dec. 12, 2017: Roy Moore loses. Moore was not Trump’s first pick to run for Senate in Alabama, but his endorsed candidate lost the Republican nomination. So Trump switched to Moore — just in time for Moore to be saddled with one of the most damaging scandals in U.S. political history. Moore lost, setting up a pattern of iffy Trump-backed candidates failing to cross the finish line.

26. Dec. 18, 2020: Oval Office fight over election denial. More than a month after Trump lost his reelection bid, he hosted a group of allies in the White House for an hours-long meeting about trying to reverse the results. Trump entertained appointing attorney Sidney Powell — already discredited — as special counsel to investigate nonexistent fraud. Soon after the meeting, Trump tweeted about a rally at the Capitol on Jan. 6, 2021.

Peter Navarro releases 36-page report alleging election fraud ‘more than sufficient’ to swing victory to Trump https://t.co/D8KrMHnFdK. A great report by Peter. Statistically impossible to have lost the 2020 Election. Big protest in D.C. on January 6th. Be there, will be wild!

— Donald J. Trump (@realDonaldTrump) December 19, 2020

25. Nov. 6, 2018: Midterm election debacle. The first midterm elections of a new presidency often go against the president. But Trump built his political brand on “winning.” When Republicans lost the House in 2018, his party got another sign that he was not able to deliver victories beyond party primaries.

24. Dec. 6, 2022: Herschel Walker loses; Trump Organization convicted. That the 2022 midterms didn’t go against the new president’s party can be attributed at least in part to Trump. His elevation of candidates like Herschel Walker in Georgia helped Democratic Senate candidates win close races. That Walker’s loss came on the same day that the Trump Organization was convicted on fraud charges only amplified the difficulty of the day for Trump.

23. Jan. 12, 2018: Disparagement of African countries. During a meeting at the White House, Trump used a vulgar term to deride people from Haiti, El Salvador and African countries, helping solidify the impression that his views of geopolitics intertwined with his views on race.

22. July 8, 2017: Trump Tower meeting reported. The New York Times’s report about a meeting at Trump Tower involving a Kremlin-linked attorney and Donald Trump’s eldest son, son-in-law and campaign chairman demonstrated one of the first concrete connections between Russian actors and the campaign. More were soon to emerge, but the Trump Tower meeting made obvious that the Russia probe wasn’t solely a “witch hunt.”

21. Oct. 2, 2018: Jamal Khashoggi is murdered. The murder of a Washington Post contributing columnist at the hands of killers working for Saudi Arabia’s crown prince forced Trump to pick between siding with a U.S. resident journalist and siding with a foreign leader who had consistently played to his ego. Trump chose the crown prince.

20. Nov. 8, 2022: Another midterm collapse. The GOP’s failures in 2022 were easy to lay at Trump’s feet, if not always fairly. It was the third election cycle in a row that Republican candidates had stumbled or underperformed — and the third in a row for which Trump’s opponents could blame him.

19. Oct. 2, 2020: Announces covid-19 diagnosis. Shortly before the 2020 election, the seemingly inevitable happened: Trump got covid-19. He had rapidly pivoted from support for containing the coronavirus to — with an eye on his reelection — a laissez-faire approach that he himself embodied. The illness forced him off the campaign trail and raised questions about his policy choices. It also made him far sicker than he admitted.

18. Jan. 13, 2021: Impeached for Capitol riot. Trump’s second impeachment, for putting the events that led to the Capitol riot into motion, was less politically damaging, given that he was already a lame duck. But numerous members of his party in the House and Senate voted to hold him to account, dealing him a rebuke to an extent that no president had previously faced.

17. Aug. 21, 2018: Paul Manafort and Michael Cohen face justice. On one day in the summer of 2018, two former Trump allies — his longtime attorney and his 2016 campaign manager — were in court. Cohen was pleading guilty to federal charges and implicating Trump in the process. Manafort was being found guilty on charges related to financial crimes.

16. April 23, 2020: Using disinfectant to treat covid. There are plenty of questions that could be raised about Trump’s handling of the coronavirus pandemic, but few compare to his musing at a news conference that maybe disinfectant could be injected into people as a way to fight the virus. It exemplified his science-averse, off-the-cuff response to the virus.

15. Nov. 23, 2022: Nick Fuentes dinner at Mar-a-Lago. Trump’s ability to avoid rebuke from members of his own party faltered after he sat down for dinner with Ye, the rapper born Kanye West who had become notorious for antisemitic comments, and Nick Fuentes, an antisemite and white supremacist. Trump’s best defense was that he didn’t screen his dinner guests, which was not reassuring.

14. Jan. 20, 2021: Joe Biden inaugurated. The inauguration of President Biden — and Trump’s quiet departure from Washington hours earlier, avoiding the traditional process of transferring power — cemented Trump’s inability to accept the will of the electorate.

13. Jan. 21, 2020: First coronavirus case in the U.S. The arrival of the coronavirus has been identified by Trump himself as the moment that his reelection became uncertain.

12. May 29, 2020: Forced to shelter in White House bunker. As protests continued in Washington following the death of George Floyd at the hands of police in Minnesota, Trump was forced to seek refuge in a bunker at the White House. It was a demonstration of weakness that ran against Trump’s heavily cultivated image of toughness and probably contributed to his decision to walk across the square outside the White House for a photo op.

11. Aug. 8, 2022: Mar-a-Lago searched. The FBI’s search of Trump’s Mar-a-Lago event space was the culmination of a months-long back-and-forth in which Trump apparently tried to retain possession of government documents. It was an unusual step, certainly, but one that reinforced the weight of the political baggage that Trump carries.

10. Nov. 3, 2020: The effort to overturn the election begins. Trump hoped that 2020 might go the way 2016 did, with his overperforming polls and securing a close victory. But he was prepared if not. For months, he stoked unfounded concern about mail ballots, allowing him the option to proclaim victory before votes were counted. Hours after polls closed on Election Day, he tried to do exactly that, setting in motion the effort to reverse his election loss.

9. Dec. 18, 2019: Impeached over Ukraine. Trump’s first impeachment in late 2019 followed a well-documented effort to get Ukraine to announce an investigation into Joe Biden before the United States would provide military and other assistance. It cemented Trump’s place in the history books, revealed how far he would go to retain power — and reflected new light after Russia’s invasion of Ukraine made obvious just how necessary such military aid was.

8. July 28, 2017: John McCain kills Obamacare overhaul. Echoing conservative media, Trump pledged to overhaul the Affordable Care Act if elected. In his first year in office, he and congressional Republicans moved to do so. But that effort collapsed in dramatic fashion when Sen. John McCain (R-Ariz.) emerged to vote down the party’s last-ditch proposal. Trump’s grudge against McCain continued even past the senator’s death.

Sen. John McCain (R-Ariz.) on July 28, 2017, voted against the Republican “skinny repeal” health-care bill. (Video: U.S. Senate)

7. June 20, 2018: Trump ends child separation. In an effort to curtail immigration, Trump’s Justice Department instituted a policy separating children from their parents, with one goal being to provide a visceral, cruel disincentive for coming to the United States. The policy came to help define Trump’s administration, and his eventual reversal of the policy did little to change that perception.

6. Aug. 12, 2017: Charlottesville. When a right-wing rally in Charlottesville led to the murder of a counterprotester, Trump was slow to criticize racist extremists whose presence had triggered violence. Ultimately, he blamed and praised both sides — the extremists and the counterprotesters.

5. Feb. 1, 2016: Loses Iowa caucuses. The very first political contest in which Trump took part, he underperformed. In the 2016 Iowa caucuses, Sen. Ted Cruz (R-Tex.) emerged victorious, beating the polls. Trump’s response? He claimed that Cruz cheated and that the results were somehow fraudulent. It was a good preview of the next five years.

4. Oct. 7, 2016: “Access Hollywood” tape released. The Washington Post’s publication of a tape in which Trump admitted groping women forced the then-candidate to release a video of apology — something he didn’t normally do. But the day included other important developments: WikiLeaks began dumping documents stolen from an adviser to Trump’s opponent, Hillary Clinton, which both shaped the rest of the election and became part of the investigation into Russian interference that would hang over Trump’s presidency.

3. Jan. 6, 2021: Capitol riot; social media ban. The riot at the Capitol will forever define Trump’s response to his election loss. But it also triggered his ban from social media, prompting him to create his own platform and inflicting damage that Trump felt very personally.

2. May 17, 2017: Robert S. Mueller III appointed special counsel. The Mueller appointment, like the McCain vote on Obamacare, nestled deeply in Trump’s brain. He railed against Mueller and the Russia probe unrelentingly. He still rails against the Russia probe, in fact. It was a signal moment when Trump realized that the federal government was not his to control. It was also when he learned he might face some accountability that, as the head of a privately owned business, he was usually able to avoid.

1. Nov. 7, 2020: Election called for Biden. Perhaps no other day in Trump’s life has had such a profound effect on him and on how others perceive him.

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