Former President Donald Trump’s tax woes lead to the hot seat again as a government audit suggests Trump might owe over $100 million due to alleged double-dipping on tax losses linked to a prominent Chicago skyscraper.

This latest revelation casts a shadow over Trump’s bid to reclaim the White House, bringing renewed attention to his business dealings. Despite leveraging his real estate mogul persona and TV stardom to fuel a political movement, Trump has staunchly withheld his tax filings.

The scrutiny intensifies as details emerge from past tax filings unearthed by investigative reporting and congressional releases. Trump’s camp, led by son Eric Trump, insists that the IRS matter was resolved long ago, only resurfacing due to political motives.

Trump’s tax woes

At the heart of the issue lies Trump’s reported maneuver of transferring property ownership to mitigate tax burdens, allegedly claiming millions in losses twice over on the Trump International Hotel and Tower. While the audit’s current status remains undisclosed, the potential repercussions loom large, with penalties potentially stacking up to a hefty sum.

This isn’t the only legal battle Trump is embroiled in. Fresh from contesting a New York court’s ruling that accused him of inflating his wealth, Trump has posted a staggering bond to stave off a massive debt collection, buying time as he appeals the judgment.

The political landscape adds another layer of complexity, with President Joe Biden highlighting Trump’s financial background, attributing his wealth largely to inheritance rather than entrepreneurial prowess. Biden’s administration has ramped up IRS funding, aiming to crack down on tax evasion among the ultra-rich, a move vehemently opposed by the Trump camp.

As the saga unfolds, Trump’s narrative of economic stewardship clashes with mounting legal woes and political adversaries, setting the stage for a high-stakes battle over his financial legacy.

Cover Photo: Depositphotos

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