Stephen Hearn

Chief Executive Officer, The Hearn Company

Hearn has ridden the waves of Chicago’s office market over decades, with the post-pandemic downturn sending some of his Loop towers into distress.

Hearn founded his Chicago-based real estate company in 1974, with a focus on distressed and underperforming commercial assets. For years, Hearn built a reputation as one of the city’s more aggressive office players, leaning into leasing risk and capital repositioning when others pulled back.

But in recent years, as vacancy surged and capital tightened, Hearn explored unconventional paths to preserve value, including proposals to convert portions of the 100-story former John Hancock Center building into medical office space tied to Streeterville’s hospital corridor.

Not every bet has landed. In 2024, Hearn and Fortress Investment Group surrendered the keys to 2 North LaSalle Street to avoid foreclosure. Another tower Hearn co-owned, at 70 West Madison Street, was hit with a foreclosure lawsuit in 2024, and the owners sold the building in 2025 at a 77 percent discount.

His signature deal came in 2013, when he acquired the office and parking components of the former Hancock building, now known as 875 North Michigan Avenue, for $145 million. Hearn and his partners poured capital into the property, upgrading common areas and stabilizing tenancy before refinancing with a $210 million loan — a transaction that allowed investors to pull out significant equity ahead of the office sector’s broader decline. 

Hearn’s career reflects the full arc of Chicago office real estate: bold contrarian bets, well-timed exits — and, more recently, the reality that even seasoned distress hunters can get caught when demand evaporates faster than capital can adjust.

— Caleb McCullough