Former brokerage head Ryan D’Aprile faces $3M West Town foreclosure

A year after Ryan D’Aprile sold his Chicago-based brokerage to Coldwell Banker Real Estate Group, seemingly reaching the pinnacle of his real estate career, he has left the industry for good.

“I’m doing my own thing,” he told The Real Deal. “I’m out.”

In 2021, at its height, D’Aprile’s eponymous brokerage did more than $1.2 billion in deals, he claimed. But legal troubles related to his previous career are still following him, with the latest being a lender threatening to foreclose on D’Aprile’s former offices in West Town, public records show.

The building at 1732 West Hubbard Street where D’Aprile ran his brokerage is now being pursued by Belmont Bank & Trust Company for foreclosure. He is also facing a separate lawsuit over disputed use of tenant improvement money at another commercial property on the North Side.

Belmont last week filed a $2.9 million foreclosure lawsuit against D’Aprile last week over unpaid mortgage debt on his 24,000-square-foot building on Hubbard Street, Cook County court records show.

His loan was set to mature in 2029, and the lawsuit alleges D’Aprile stopped making payments in September. He told The Real Deal that rising taxes forced him to put the building on the market. When it wouldn’t sell, he decided to let the bank take back the keys.

In 2019, the building’s property taxes were $39,000. By 2022 they had risen to $164,000, according to records from the Cook County assessor’s office. In 2021, he tried to appeal his assessment to get a lower tax value and was unsuccessful.

“It’s been on the market since the taxes went up,” he said. “We have a problem in the city of Chicago.”

An LLC in D’Aprile’s name is listed as a defendant in the foreclosure along with three guarantors on the loan; D’Aprile, his wife Lindsay and Midwest Lending Corporation.

According to the lawsuit, Belmont wants to force a sale of the building, but also raises the possibility of going after the guarantors’ assets to cover $2.9 million in damages. Representatives of the lender were not immediately available for comment.

The foreclosure suit filed Jan. 17 is the latest in a string of legal woes for D’Aprile.

He is also the subject of a yearslong legal battle with North Side landlord Wildcat Properties. Wildcat’s lawsuit states that the company secured a $260,000 loan for D’Aprile to make tenant improvements to office buildings, including one at 3847 North Lincoln Avenue in the North Center area. Half of those funds were set aside for the Lincoln Avenue property D’Aprile rented.

He then allegedly failed to secure the necessary building permits that would allow him to accept the funds and work on improvements to the space.

The case has been delayed and dragged out with new motions since 2022. Responses filed by D’Aprile’s attorney deny that any delays in securing the necessary building permits were D’Aprile’s fault.

While Wildcat alleges that D’Aprile did not attempt to secure the permits in a timely manner, he told The Real Deal that he blames the city’s approval process, and felt it took too long.

Although that case is ongoing, D’Aprile resolved two other lawsuits in the past year.

In August, he dropped a complaint he brought against his brokerage’s former vice president of agent training and development, Pete Moulton. He initially alleged that Moulton “aggressively recruited” former agents of his firm after leaving for competing brokerage Fulton Grace Realty, which violated the terms of a non-soliciation agreement Moulton had signed.

“I made it clear that it was in his best interest to drop the lawsuit and he did,” Moulton told The Real Deal. He called D’Aprile’s claim “completely fabricated.”

In November, another lawsuit was dismissed between D’Aprile and co-owners of Hubbard Street Tite, a title company that he co-founded while he ran his own real estate firm.

His former co-owners in the title company alleged that he did not properly inform them that he planned to sell his brokerage to the Coldwell affiliate and that he started referring business to Coldwell’s preferred title company instead of Hubbard Street Title. They sought $5 million in damages in the initial filing. It is unclear what the plaintiffs were ultimately rewarded, if anything.

Legal representatives of Hubbard and Wildcat did not respond to requests for comment.

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