New York, NY – Former president Donald J. Trump’s reputation as a “Teflon Don” who can evade consequences seems to be unraveling with his latest legal setback – a whopping $355 million fine for business fraud levied by a New York judge last week. This massive penalty is just the latest in a series of high-profile losses for the embattled ex-president since 2018.
The recent fraud ruling relates to Trump overvaluing properties to obtain favorable loans and tax breaks. With interest, his total penalties could swell to over $450 million. Coming on the heels of Trump Organization tax fraud convictions last December, it signals deepening legal woes for the former reality TV star.
Trump also suffered major political defeats in recent years. In the 2018 midterms, voter antipathy toward his administration led to Democrats flipping the House. In 2020, Trump became the first modern president to lose reelection. That same year, two Trump-backed Senate candidates lost hotly contested Georgia runoffs, handing Democrats razor-thin control of Congress’s upper chamber.
Tax Fraud Convictions and Lawsuits Mount
Beyond the massive civil penalties for financial statement fraud, Trump’s business also suffered a blow when a New York jury convicted the Trump Organization of tax crimes in late 2022. While Trump himself avoided charges in that case, prosecutors charged his company with facilitating executive tax avoidance schemes and falsifying records.
The guilty verdicts and $1.6 million fine add further reputational damage as Trump attempts a political comeback. They also showcase his vulnerability to New York’s investigatory apparatus after losing his presidential protections.
This pattern repeated in 2022’s midterms when key Trump-endorsed candidates lost races that could have given Republicans commanding congressional majorities. Instead, Democrats retained the Senate while eking out only a slim House majority.
Beyond politics, Trump lost high-profile defamation suits brought by writer E. Jean Carroll, who accused him of past sexual assault. Juries ordered Trump to pay Carroll over $5 million in damages last year, with another $83 million verdict arriving in January.
With a criminal trial looming this March over illegal hush money payments to adult film star Stormy Daniels, Trump’s legal bills continue ballooning. Further prosecutions related to the Capitol attack and document mishandling may follow. After years of seeming invincibility, his foes appear to be gaining ground.
For a politician who built his brand on winning, Trump’s lengthening streak of defeats in courts and at ballot boxes does not bode well for his rumored 2024 presidential run. Still, writing off Trump risks repeating old mistakes. This wounded, cornered figure seemingly thrives on bitter battles with the establishment he detests. Perhaps another unlikely comeback awaits.
