Donald Trump surprised the world by winning the US presidential election in 2016, establishing a mystique as somebody who can break rules, violate norms, take crazy risks, and still win.
The mystique is gone.
Since 2018, Trump has endured a string of losses that should bury the idea that Trump somehow defies gravity in politics and business. The latest legal judgment against him, a gigantic $355 million fine for business fraud in New York state, could threaten the entire enterprise Trump’s father Fred established in the 1920s if it survives an appeal.
More setbacks seem likely. Trump faces 91 criminal charges in four separate cases and has astronomical legal bills. While he’s cruising to the Republican presidential nomination, and even leading the Democratic contender, President Joe Biden, in some polls, Trump is also amassing a record as a serial loser. Seven prominent examples:
The 2018 midterm elections. Voter disgust with Trump in the second year of his presidency helped Democrats flip 40 seats and recapture the House of Representatives from Trump’s Republican party. While it’s normal for the president’s party to lose ground in the midterms, exit polls in 2018 revealed unusually high levels of opposition to Trump, which fueled record turnout. Control of the House allowed Democrats to block Trump’s legislative agenda for the last two years of his presidency.
The 2020 presidential election. Trump was the first incumbent to lose a reelection bid since George H. W. Bush in 1992.
The 2020 Senate race. Control of the Senate in the 2020 election came down to two runoff races in Georgia that weren’t concluded until early January 2021. Two Democratic challengers ended up beating two incumbent Republicans, an improbable Hollywood ending for Democrats that gave them a one-vote majority and control of both houses of Congress. Many analysts, including Republicans, blamed Trump’s election denialism and his squabbling with fellow Republicans for the Georgia Senate losses. Those two Senate seats allowed Democrats to pass a huge stimulus bill in 2021 and a massive set of green energy incentives in 2022 that never would have happened had Republicans kept control of the Senate.
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Former US President Donald Trump speaks to the press as he arrives at Manhattan Criminal Court in New York City on February 15, 2024. (ANGELA WEISS/AFP via Getty Images) (ANGELA WEISS via Getty Images)
The 2022 midterms. Trump endorsed a variety of Republicans in 2022, including many incumbents with no chance of losing. In competitive races, however, most of Trump’s choices lost, including Senate candidates Herschel Walker in Georgia, Mehmet Oz in Pennsylvania, and Blake Masters in Arizona, allowing Democrats to keep the Senate. Republicans did win control of the House, but just barely, with Democrats overperforming. Once again, exit polls showed that Trump’s involvement hurt Republicans. The GOP’s tiny majority set the stage for the defenestration of House Speaker Kevin McCarthy last October — and the subsequent paralysis that Joe Biden is now exploiting in his reelection campaign.
Trump Organization fraud case. In December 2022, a New York jury convicted Trump’s real-estate company on 17 charges of tax fraud and other crimes. That’s the same case in which former CFO Allen Weisselberg pled guilty to tax crimes. A judge fined the company $1.6 million, the maximum allowed. Prosecutors didn’t charge Trump personally.
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E. Jean Carroll lawsuits. Last year, a federal jury found that Trump sexually abused and defamed the New York writer, ordering him to pay her $5 million. Trump continued to lambaste Carroll publicly, and in January, another jury ordered Trump to pay Carroll an additional $83.3 million. Trump has finally stopped attacking Carroll.
New York state fraud lawsuit. Last September, a judge found that Trump, his company, and several executives defrauded banks and insurance companies by substantially and repeatedly overstating the value of certain properties. On Feb. 17, the same judge hit Trump with $355 million in fines, plus interest likely to push the total over $450 million.
Trump famously said in 2016 that he could shoot somebody on Fifth Avenue in New York and suffer no consequences. He and his supporters should reassess. During the last few years, Trump has repeatedly suffered consequences for cheating, bullying, lying, and overestimating his capabilities. The stakes are about to get higher still.
In March, Trump will face a New York City criminal trial related to hush money payments during the 2016 election that Trump claimed as business expenses. A guilty verdict could entail up to four years in prison. Pending are one federal trial on Trump’s role in the Jan. 6, 2021, riots at the US Capitol and another on his misuse of classified documents after he left the White House. Then there’s the Fulton County, Georgia, trial on election fraud.
If Trump once seemed like he could get away with anything, he doesn’t anymore. Trump seems to win points with his supporters for mouthing off to judges and prosecutors, but he’s losing cases and an enormous amount of money. Some analysts speculate that Trump’s legal catastrophes may force him to declare personal bankruptcy.
As for the 2024 election, Trump seems set to defy the rules again by becoming the only major presidential candidate being prosecuted — and possibly convicted — of serious crimes while campaigning. He could even beat Biden in November and claim a second presidential term. But Trump is no longer an underdog, a dynasty destroyer, or a swamp-drainer. The establishment he wants to destroy is fighting back and racking up a sizable string of victories.
Rick Newman is a senior columnist for Yahoo Finance. Follow him on Twitter at @rickjnewman.
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