What's Really Going On With All Of Donald Trump's Real-Estate Challenges?

Ever since Donald Trump pursued a political career that led to his run as the 45th president of the United States, pretty much every aspect of the TV-star-turned-politician's life has been dissected. Critics of Trump have endlessly condemned him for misogynistic and xenophobic comments, as well as an apparent history of public lies and sexual assault allegations. Trump's money woes, including his tax return fiasco, have also been a huge topic of conversation.

Despite being the son of Fred Trump, a former prominent real-estate developer in New York City, who went from hosting "The Apprentice" to being America's commander-in-chief, Trump has actually experienced more money issues than some imagine. As Yahoo! Finance reported, the New York native has declared bankruptcy six times throughout his career. The first came in 1991, more than a decade after Trump acquired three casinos — Taj Mahal, Trump Plaza, and Trump Castle — in Atlantic City, New Jersey in the 1980s.

After the Taj Mahal declared bankruptcy in 1991, the Trump Plaza and Trump Castle quickly followed, as they were both bankrupt in 1992. Because loan lenders "restructured the debt rather than liquidate" it, as Yahoo!'s report stated, Trump put his casino holdings into a new company, though that went bankrupt in 2004. The reemerged company late went under in 2009, and Trump's sixth bankruptcy was NYC's Plaza Hotel in 1992. According to new reports, the world may be watching his seventh bankruptcy unfold — keep scrolling for details.

Donald Trump is apparently plotting his return to politics in hopes to get elected as president in 2024, but he may want to shift his focus to his real-estate challenges. According to data from banking giant Wells Fargo, a $100 million loan on Trump Tower in New York City has been placed on a debt watch list. Bloomberg reported the finding on September 17, revealing the decision was made in an effort to "lower average occupancy."

Wells Fargo, the master servicer of the loan, stated occupancy in Trump's Fifth Avenue building dipped to 78.9% from 85.9% over the last year, bringing the income to a total of $7.5 million in the first quarter of 2021. That is much lower compared to the tower's real-estate income for 2020, which was reported to be $33.7 million.

The extent of Trump's money and real-estate woes doesn't end there, though. As Insider reported, the Trump Organization sued the maker of Ivanka Trump's shoe line for $1.5 million earlier in 2020 over claims of unpaid rent. Trump's financial woes have also led to Illinois, where a property tax for his Chicago office tower was dropped by $300,000 after the value of the building was cut by nearly 37%. As the Chicago Sun-Times reported, the space was worth $12.5 million, down from $19.9 million, as most of the building has "remained vacant and left unfinished."