Jonathan Bennett

President at AmTrustRE

Speaker

Jonathan Bennett is President of AmTrustRE, a national owner-operator with more than 12 million square feet of commercial, mixed-use, and residential properties across the Northeast, Midwest, and Sunbelt. Jonathan oversees the firm’s portfolio strategy, investment activity, capital improvements, and leasing initiatives, while leading a team of more than 100 professionals across New York and Chicago.

In New York, Bennett has expanded AmTrustRE’s Midtown footprint with acquisitions including 260 Madison Avenue and 360 Lexington Avenue, while driving strong leasing momentum across the portfolio. At 250 Broadway, he recently secured major leases with WeWork and Rose & Rose, further reinforcing the appeal of high-quality, amenitized office space.

In Chicago, Bennett is leading the adaptive reuse of the historic Field Building, now 135 S. LaSalle, into 386 residential units and 92,000 square feet of commercial space, alongside major repositioning efforts at One East Wacker and 33 North Dearborn. These multi-million-dollar upgrades have already spurred significant leasing activity and enhanced tenant experience.

Across markets, Bennett is known for transforming underperforming assets into modern, high-performing destinations through strategic reinvestment, repositioning, and adaptive reuse.

A seasoned real estate executive with more than 20 years of experience, Bennett previously served as Managing Director at Nakash Holdings, where he oversaw a multi-billion-dollar, multi-asset portfolio spanning retail, office, multifamily, and hospitality. He began his career in investment banking at American Express, building a strong foundation in capital markets and asset management.