Andy Gloor

Chief Executive Officer, Sterling Bay

Gloor is viewed as the man who turned Sterling Bay from a scrappy local developer into an institutional behemoth backed by the likes of JP Morgan’s investment arm and other blue-chip financiers.

He joined the firm in 2002 and under his direction in the 2010s it ramped up on raising institutional capital, while landing marquee tenants like Google and McDonald’s and delivering projects such as 1K Fulton and 111 North Canal.

Gloor’s toughest test has been Lincoln Yards, Sterling Bay’s sprawling North Side megadevelopment along the Chicago River’s North Branch. After years of planning and infrastructure work, the project stalled amid rising interest rates and strained capital markets. In early 2025, Sterling Bay handed part of the site back to lender Bank OZK via deed in lieu of foreclosure — a rough public setback for the firm.

Another new buyer, John Novak, has emerged for more financially troubled Lincoln Yards land, and there’s speculation across the Chicago real estate scene on whether Sterling Bay will retain a stake under the new ownership.

Gloor characterized the move as a pause rather than a retreat and has said Sterling Bay intends to re-enter capital markets when conditions improve. Whether Lincoln Yards ultimately fulfills its original ambitions remains an open question, but the episode has reshaped perceptions of risk even for Chicago’s most established developers.

— Emma Whalen