Joseph Chetrit, founder of the Chetrit Group, is one of New York’s most enigmatic and influential real estate investors, known for executing some of the city’s largest and most complex property deals with minimal public profile. After building an early fortune in textiles, Chetrit shifted into real estate in the 1990s, assembling a multibillion-dollar portfolio that includes office towers, residential conversions, hotels, and landmark properties across Manhattan, Miami, Los Angeles, and beyond. His firm has been involved in major transactions such as the Sears Tower sale, the Chelsea Hotel redevelopment, and large-scale waterfront projects. Chetrit’s combination of discretion, scale, and contrarian timing has made him a defining—if quietly spoken—force in American real estate.

Jerry Speyer, cofounder and chairman of Tishman Speyer, is one of the most influential real estate developers of the modern era, shaping skylines across New York, major U.S. cities, and global financial hubs. Since launching the firm in 1978 with his father-in-law, Robert Tishman, Speyer has overseen iconic projects such as Rockefeller Center, the MetLife Building, and Frankfurt’s MesseTurm, while expanding the company’s portfolio to more than 200 million square feet of office, residential, and mixed-use assets worldwide. Known for his disciplined investment approach, civic leadership, and long-term urban vision, Speyer remains a defining figure in institutional real estate.

Jeff Sutton, founder and president of Wharton Properties, is one of New York City’s most powerful retail real estate owners, known for assembling a blue-chip portfolio through off-market deals and long-term tenant relationships. Starting from modest beginnings, he built his empire by securing prime Manhattan corners and partnering with luxury brands and national retailers such as Nike, Zara, and American Eagle. Sutton’s strategy—favoring ground-floor retail in irreplaceable locations and maintaining conservative leverage—has made Wharton Properties a dominant force in high-street retail and one of the most valuable privately held real estate portfolios in the city.

Jed Walentas, CEO of Two Trees Management, is one of New York City’s most influential real estate developers, known for transforming Brooklyn’s DUMBO neighborhood from industrial waterfront to one of the city’s most desirable creative and residential hubs. Building on the vision of his father, David Walentas, he led marquee projects such as the Domino Sugar Refinery redevelopment on the Williamsburg waterfront—blending mixed-use design, public spaces, and architectural ambition. With a reputation for long-term, community-focused urban development, Walentas has shaped modern Brooklyn’s identity while solidifying Two Trees as a powerhouse in New York real estate.

Jay Paul, founder of the Jay Paul Company, is one of Silicon Valley’s most influential and discreet real estate developers, known for creating some of the region’s most valuable and sought-after corporate campuses. Since the 1970s, he has transformed underutilized land into cutting-edge office complexes occupied by tech giants such as Google, Amazon, and Apple, while reshaping skylines with projects like San Francisco’s landmark 181 Fremont tower. Renowned for his long-term vision, premium building standards, and exceptional tenant relationships, Paul has built a multibillion-dollar empire that underpins the infrastructure of the modern tech economy—all while maintaining a notably private personal profile.

Igor Olenicoff, billionaire real estate developer, is the founder and owner of Olen Properties, a privately held company with a vast portfolio of commercial and residential properties across the United States. Based in Newport Beach, California, Olen Properties controls tens of millions of square feet of office space and thousands of rental units, with a strong presence in California and Florida. Known for his aggressive growth and hands-on management style, Olenicoff has built one of the nation’s largest private real estate empires while maintaining a low public profile.

Roy Carroll II, founder, president, and CEO of The Carroll Companies, has built a diversified real estate empire spanning multifamily housing, commercial developments, self-storage, and luxury communities. Based in Greensboro, North Carolina, the privately held company oversees billions in assets with projects across the Southeastern United States. Known for his entrepreneurial drive and long-term investment vision, Carroll has positioned his firm as a leader in regional real estate while also supporting civic and philanthropic initiatives that strengthen local communities.

Harry Macklowe, New York real estate developer and art collector, is known for bold, high-stakes deals that reshaped the Manhattan skyline. Founder of Macklowe Properties, he developed iconic projects such as 432 Park Avenue, one of the tallest residential towers in the Western Hemisphere. His career has been marked by both spectacular successes and dramatic setbacks, including a leveraged $7 billion office portfolio purchase in 2007. Beyond real estate, Macklowe gained global attention for his blue-chip art collection, reinforcing his image as one of New York’s most colorful and audacious moguls.

Geoffrey H. Palmer, founder of G.H. Palmer Associates, is one of Los Angeles’s largest apartment developers, with more than 13,000 units across the metro. He stamped downtown with Italianate mega-complexes like the Medici, Orsini, Piero, Da Vinci, and Lorenzo, and reshaped policy with the 2009 appellate win Palmer v. City of Los Angeles, which limited rental inclusionary mandates under California’s Costa-Hawkins Act. A prolific Republican donor, he remains a powerful—if polarizing—force in L.A. real estate.

David Walentas is the self-made real estate developer behind Two Trees Management, the Brooklyn firm that transformed Dumbo and Williamsburg from industrial decline into high-end residential and creative districts. A University of Virginia alumnus, Walentas began with a small Manhattan partnership in 1968 and leveraged $12 million to acquire nearly 2 million sq ft in Dumbo, reshaping it through bold vision and rezoning advocacy.

Stephen M. Ross is a real estate magnate, philanthropist, and sports team owner known for founding Related Companies, the real estate firm behind iconic projects like Hudson Yards, and for owning the Miami Dolphins. With a significant influence in real estate, sports, and philanthropy.