Matthew Fiascone

Fiascone has been navigating a volatile environment for subsidized housing.

His firm Habitat got entangled in high-profile litigation tied to lead paint exposure at Chicago Housing Authority properties it managed, including a 2025 jury verdict and subsequent lawsuits that sharpened scrutiny of the firm’s CHA work. In late 2024, the company cut ties with the CHA entirely, a move that reduced political and legal exposure but also removed a source of income. In 2025 a jury found The Habitat Company not liable, placing responsibility with the Chicago Housing Authority.

At the same time, Fiascone has pushed forward with new development and recapitalization efforts. Habitat covered a roughly $20 million debt gap on a Wacker Drive multifamily property as refinancing conditions tightened, signaling a willingness to protect long-term holdings rather than hand keys back. The firm has also pitched new projects, including townhomes at the former Solo Cup site in Highland Park that drew local opposition over density and scale. Highland Park City Council in early 2026 unanimously approved Habitat’s project, set for groundbreaking later in the year.

Fiascone’s leadership of the firm, whose portfolio spans affordable, mixed-income and market-rate housing, coincided with a time of larger transition for the company in early 2025 following the death of longtime chairman and founder Daniel Levin at age 94. That closed a chapter for Habitat as it navigated leadership continuity amid mounting legal and capital pressures.

Fiascone joined Habitat in 2011 after decades at Inland Real Estate Development Corporation, where he oversaw more than $1 billion in joint ventures, and he has since become the public face of Habitat’s development, capital strategy and asset management.