Trump's finances under fire AGAIN as it's revealed he may owe $100M after 'double dipping' on tax breaks - as experts give their predictions

Donald Trump could owe a staggering $100 million in taxes after allegedly 'double dipping' on deductions, according to an IRS audit.

The inquiry, revealed by The New York Times and ProPublica, centers around the former president's glittering skyscraper in Chicago.

The 92-story structure opened over budget and during the recession, resulting in huge losses that Trump attempted to claim back.

However, the IRS, and several tax experts, believe he may have effectively written off the same losses twice resulting in massive tax breaks.

'I think he ripped off the tax system,' Walter Schwidetzky, a law professor at the University of Baltimore and an expert on partnership taxation, told the Times.

The first write-off took place in 2008 when Trump claimed the $847 million condo-hotel met the tax threshold of 'worthless' as spiraling debts meant he would never turn a profit.

Trump secured the former site of the Chicago-Sun Tribune in 2001 and made it the centerpiece of his TV show The Apprentice, offering the winner the 'mind-boggling job' of managing the facility.

Initially slated to open in 2007 at a cost of $650 million, various setbacks saw the deadline and the budget inch further and further away.

The arrival of the recession saw already sluggish sales of the condos stall further and Trump began to default on his loans. 

This allowed him report losses of up to $651 million for the year, The Times and ProPublica found. 

He would eventually go on to sue his lenders Deutsche Bank over the loans, claiming the recession was a force majeure, which the bank and its contemporaries had a hand in orchestrating.

His 2008 tax return saw him file business losses of $697 million, with experts suggesting the bulk of this came from the tower since this information is not publicly disclosed.

However just two years later, Trump's accountants appear to have attempted to extract further tax benefits from the losses by transferring the company that owned the tower into a new partnership.

This apparently allowed him to declare $168 million more losses over the next 10 years, according to the Times.

If he had left the set-up as it was in 2008, he would not have been able to claim the shortfall as losses again.

Continued losses meant he was allegedly able to evade tax liability for income through other sources such as his entertainment career and the unpaid debt from the tower. 

In 2010, his lenders forgave around $270 million of these debts, however, Trump was able to utilize a stimulus bill brought in by Obama post-recession to spread this over five years.

The 2010 merger maneuver is thought to be what set the IRS onto Trump's trail and was referenced in a memo by the federal agency exploring the legality of the strategy.

Trump was not named in the memo, but the Times identified him using details from New York attorney Letitia James' 2022 lawsuit against Trump and a number of Trump Organization executives for alleged financial fraud. 

The Technical Advice Memorandum, which is used to outline the IRS' position where the law is unclear, states that the agency believes the merger broke laws to prevent double dipping on tax-reducing losses.

The audit was mentioned in a congressional report in December of that year, however details on how it progressed would not be publicly available unless Trump choses to challenge to findings in open court.

The 'worthless' classification used by Trump occupies a gray area of tax law that states it can be partly decided by its owner.

However, several tax experts have taken a dim view of the tactics put in play by the Republican nominee.

IRS veteran Monte Jackel stated that including the debt in the deduction was 'just not right.'

'This matter was settled years ago, only to be brought back to life once my father ran for office,' Trump's son Eric, executive vice president of the Trump Organization, said.

'We are confident in our position, which is supported by opinion letters from various tax experts, including the former general counsel of the IRS.'

Interest in Trump's tax returns was piqued in 2016 during his run for the White House when he became the first candidate to defy tradition by refusing to publish citing an ongoing audit. 

The revelation is the latest threat to the presidential hopeful's finances and follows several expensive legal rulings including a $454 bill from James' civil fraud case and  $83 million in damages for defaming sexual attack accuser E. Jean Carroll.

He is also currently facing a criminal trial in Manhattan over alleged hush money payments he made to adult actress Stormy Daniels in the run up to the 2016 election. 

A rep for the Trump Organization did not immediately respond to the DailyMail.com's request for comment.