Phil Denny

Denny earned the nickname “King of the West Loop” by buying and holding land in Fulton Market long before the neighborhood became one of Chicago’s most expensive submarkets.

A Chicago-based investor and principal at Peppercorn Capital, Denny assembled and held a dense collection of retail, office and mixed-use sites in and around Fulton Market well ahead of the area’s transformation. Rather than chasing large-scale development, his strategy centered on owning well-located parcels and street-level buildings, a bet that paid off as upzoning and institutional demand reshaped the district.

He has selectively cashed out — including a $10.3 million West Loop land sale in 2022 — while reinvesting nearby. More recently, he expanded beyond his core with a River North-area acquisition previously owned by Goldman Sachs, which he says quickly rebounded to nearly full occupancy.

The post-pandemic market has tested local owners like Denny. Office leasing slowed, financing tightened and development timelines stretched. In response, he has leaned into adaptive reuse and unconventional tenants, including backing a manufacturing incubator at 32 North Ashland Avenue.

Denny remains outspoken about why he stays geographically concentrated. “Why on earth would you ever leave Fulton Market or the West Loop?” he said, arguing that deep familiarity with zoning, parcels and politics lowers risk and reveals opportunities “between the cracks.”

As the proposed United Center redevelopment threatens to reshape surrounding land values — and reopen old turf battles with existing industrial users — Denny’s portfolio sits squarely in the path of change.