Jay Sugarman

Jay Sugarman is the chairman and chief executive officer of both iStar and Safehold. The former is a real estate investment firm dating from the mid-1990s, and the latter is a publicly traded real estate investment trust that iStar launched in 2017 to specifically target investment in ground leases.

Before starting iStar, Sugarman managed private investment funds for the Burden and Ziff families. And, before that, he was an academic standout at Princeton, where he was nominated for valedictorian, and then at the Harvard Business School, where he graduated with distinction. Sugerman is also chairman and majority owner of the Philadelphia Union professional soccer franchise.

But, for commercial real estate purposes, he’s best-known for iStar and Safehold’s ground lease investments.

Sugarman’s Safehold picked a propitious time to engage the sector. The ground lease model has become increasingly more sophisticated and remunerative in recent years, especially for investors who can set themselves up in deals without the deep-seated risks and complications of eras past, which included sometimes opaque ownership structures for the land being leased.

By March 2021, about 40 percent of Safehold’s portfolio of around 75 ground leases was in the Northeast. These were together worth $3.2 billion in the fourth quarter of 2020.