Guess who’s betting on Trump Tower?

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It’s been eight years since ground was broken on the Trump International Hotel and Tower, which was one of Donald Trump’s last major (and risky) real estate moves–one that left him with debt-related lawsuits and an unexpected number of empty condos. But the famed businessman is back, doing what he does best and making real estate bets.

The curious thing is: Mr. Trump is in Chicago doubling his wager on the Trump Tower.

Mr. Trump originally invested $73 million in the tower, and this from his own pocket. He also acquired $770 million in loans–a $640 million construction loan was backed by Deutsche Bank AG and $130 million of junior debt was originated by Fortress Investment Group.

Wall Street Journal has now reported that in February of this year, Mr. Trump paid another $48 million to buy out the junior creditors. He still owes approximately $125 million on the construction loan, which is due July 2013.

Throwing in his chips as he is, Mr. Trump is apparently confident in the real estate market’s recovery and believes that demand for condos like those at Trump Tower–which range in price from $400,000 to more than $3.5 million–will rise quickly.

Trump Tower features 486 residential condos and, at the end of 2011, buyers had closed on 337 of them. Just last month, Chicago Bulls star Derrick Rose purchased a $2.8 million unit on the 84th floor and also hinted at plans to purchase the single-bedroom unit next door.

Along with its traditional units, the tower also includes 339 hotel-condos on floors 18-27. These are sold to investors, who occupy the unit at will, and are then rented out to guests while the owner is absent. At the close of 2011, only 159 of these units had sold.

Of course, Trump Tower condos are not without competition in the Chicago market. According to Appraisal Research Counselors, a Chicago-based appraisal firm, there are currently 2,400 condos listed in the local market and will take up to three years to sell.

In a recent interview, Mr. Trump declared that his original investment represents “a sunk cost.” The question now is, does Mr. Trump expect to profit from his new wager.

“Call me in five years,” he said.