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 smackdown is his conviction in a New York City criminal trial on 34 counts of falsifying business records related to the notorious Stormy Daniels hush money payment right before the 2016 election. A jury found that a series of checks Trump signed to cover the payment were falsely labeled as legal expenses on his company's books, amounting to criminal felonies.
Trump could face jail time if his appeal fails to overturn the verdict, but it seems more likely he'll get off with probation. But jail time is still a possibility in three other criminal trials where Trump faces more than 50 additional criminal charges. He also faces astronomical legal bills.
Trump will get a much-needed win in July, when the Republican Party is due to make him their official candidate in the 2024 presidential race. But his mounting record as a serial loser should worry supporters. Here are seven other 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.
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.
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 pleaded 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 continued to bash Carroll, raising the possibility she could come back for even more.
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 that pushed 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.
Coming up next 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, Ga., trial on election fraud. Those probably won't get started until after this year's election, and Trump could withdraw the two federal cases if he becomes president again.
Trump seems to win points with his supporters for mouthing off to judges and prosecutors and proclaiming himself a political martyr, but he’s losing cases on the facts and elections on poor politicking. Some analysts speculate that Trump's legal catastrophes may force him to declare personal bankruptcy.
As for the 2024 election, Trump is defying the odds again by being the only presidential candidate of a major political party to be a convicted felon. But Trump is no longer the establishment wrecker he claimed to be in 2016. 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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