Pat Ryan, the billionaire insurance mogul behind Aon and Ryan Specialty Group , is no stranger to bold bets. But his latest move wasn’t about business; it was about real estate, and it came with a steep loss.

Ryan and his wife, Shirley, the namesake of the Shirley Ryan AbilityLab , sold their three-bedroom condo on the 62nd floor of 900 N. Michigan Ave., better known as the Bloomingdale’s building. The deal closed on Aug. 19 for $1.75 million. That’s about 60 percent less than the $4.4 million they paid in 2018, according to Crain’s Chicago Business.

This marks the couple’s second time selling at a steep markdown in the building. Just last December, the couple sold another condo on the same floor for $1.3 million, well under the $1.9 million they paid back in 1

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