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Trump's slippage was stark. In 2014, Trumps RevPAR of $296.39 ranked first among the eight hotels, according to STR data. The hotel ranked second in 2015. But by 2018, it ranked sixth, with a RevPAR of $258.38.

The Trump Chicago, which opened in 2008, may also have lost business to new luxury competitors that opened before and during his presidential campaign, according to Detlefsen. Seven upper-end hotels opened between 2013 and 2016, including the Langham Chicago a block away, the Loews in Streeterville and the Virgin and London House in the Loop.

Thats quite a bit of new supply over a short period of time in the upper upscale and luxury chain scales, Detlefsen wrote in his email. However, (Trumps peer group) ekes out a tiny RevPAR gain in 2016 when Trump RevPAR plummets.

The pandemic pummeled all downtown Chicago hotels, with Trumps losing $9 million in 2020 on an EBITDA basis. RevPAR at Trump fell 68% in 2020, versus a 77% decline for its competitors, according to STR data provided to the assessor.

The documents did not include complete data for 2021 or 2022, so it's difficult to determine whether the recent criminal investigations of the former president have hurt the hotel's results further. Through the first eight months of 2021, RevPAR at the Trump Chicago rose 55% over the same period in 2020, versus a 77% gain for its competitors, according to STR data. The downtown hotel market has rebounded further since then, lifted by a pickup in leisure travel.

Trump has not been charged with criminal wrongdoing and has denied allegations that he committed crimes during and after his presidency. He has said the multiple probes are part of a broader effort by his political enemies to bring him down.

Trump owns a majority of the rooms in the Chicago hotel, part of the Trump International Hotel & Tower at 401 N. Wabash Ave. When he developed the 92-story skyscraper, he had planned to sell off all the rooms as condominiums, but sales stalled as the market plunged during the financial crisis, and he retained ownership of 175.

The Trump Chicago has turned out to be a poor investment for many people who did buy hotel rooms in the building. Investors can buy and sell the rooms as they would with residential condos, and many who have sold have taken big losses. In March 2021, a 21st-floor hotel unit sold for $115,000, down from $248,000 in a prior sale in 2016. At the end of September, a bigger unit on the same floor sold for $415,000, down from the $874,000 that the seller paid Trump for the unit back in 2008.

Setting aside Trump's political controversies, a bigger problem for the Trump brand now may be that it represents something different than it did before he embarked on a political career, said branding consultant Allen Adamson. Trump has extremely passionate followers, but they're not the target demographic for his high-end hotels.

"As his political brand has overwhelmed his business brand, his core target is not luxury buyers," said Adamson, co-founder and managing partner of Metaforce, a New York-based brand consulting firm. "He may be better at selling pillows and beer than high-end luxury."

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As Donald Trump took over the White House, his Chicago hotel suffered - Crain's Chicago Business