Jay Sugarman on MLS strategy
From Thinking Differently with Philadelphia Union's Jay Sugarman (Ep. 16) · · Bryn Mawr Trust
“So when I look at the Eastern Conference in MLS, it's over half the teams are owned by NFL owners or giant conglomerates. The idea that we're going to outspend them and get better players than them just didn't make sense to me. So we had to find something different, a different path. And you know, we came up with a strategy built on the pillars of development and style of play that would be different and innovation both because we think it will work and because it was the only path really available to us. And I love that last line in the Moneyball where Brad Pitt says, you know, if the if the New York and LAS win, everybody pops the champagne cork and it's great, but if we win, we change the game. And I think one of the things we're trying to do at the Philadelphia Union is change the landscape of American soccer to build American players who will succeed on an international scale and to help elevate uh the sport in this country to become one of the top sports.”
On , Jay Sugarman, Chief Executive Officer & Chairman at SAFEHOLD INC, spoke about MLS strategy during Thinking Differently with Philadelphia Union's Jay Sugarman (Ep. 16) on Bryn Mawr Trust.
About Jay Sugarman
Jay Sugarman, chairman and CEO of Safehold and principal owner of the Philadelphia Union, discussed his career and approach to decision-making on the "Planning Perspectives" podcast in April 2026. He described founding the real estate company Starwood in the late 1980s as a contrarian move, saying he and his partner saw opportunity when real estate was "finally hated enough." He said he aimed to modernize real estate finance by applying corporate-world methods, similar to his current work with ground leases. Sugarman also explained his investment in the Philadelphia Union, stating that during the 2000s internet boom he believed soccer would grow in the U.S. as the world's sport. He said the club chose to focus on youth development, style of play, and innovation rather than trying to outspend larger ownership groups in the Eastern Conference.