Andrea Guerra

It’s hard to recognize Jeff Sutton at No. 10 in the Power 100 for selling $1.8 billion in real estate to luxury brands without acknowledging the people he sold it to.

Prada has earned honorable mention for buying 724 Fifth Avenue for $425 million and 720 Fifth Avenue for $410 million, deals that have changed the outlook of commercial real estate in New York City and nationally among many looking to invest.

While it’s unclear who negotiated the deal for the Italian fashion house, it is obvious that Prada’s business strategy under CEO Andrea Guerra goes beyond handbags, and that Prada will pay a lot of cold, hard cash to own the spaces it occupies.

Prada knew what it was buying in 724 Fifth, having leased the ground-floor retail space for its New York City flagship store since the late 1990s. In December, Prada dropped Sutton a note encouraging a meeting when he was going to be in Milan, Italy. Upon arriving in northern Italy, Sutton and Prada met and came to an agreement within a single day. Hands were shaken and money was transferred three weeks later, according to a source.

One thing seems certain: Italians like to gossip, and word apparently got around that deals were being made.

With 720 Fifth Avenue, Prada also negotiated for an annex next door on East 56th Street that Sutton had managed to hold onto when he sold his stake in the Crown Building in 2019.

During the trip to Italy, Eastdil Secured’s Will Silverman and Gary Phillips set up another meeting in Paris for Sutton with Kering, the company that owns Gucci, Balenciaga and Alexander McQueen. Kering ended up buying 715-717 Fifth Avenue for $963 million.

The Kering deal would have the added benefit of rescuing Sutton and his joint venture partner SL Green Realty from distress as New York Life Insurance Company was trying to foreclose on the property and complicating their efforts to refinance a $300 million loan. 

As for Prada’s Guerra, he does have a bit of a background in commercial real estate. Prior to becoming that company’s CEO in January 2023, he worked at fellow luxury lifestyle vendor LVMH. One of his roles there included CEO of LVMH’s hotel and hospitality initiatives. Guerra was also executive chairman of epicurean food emporium Eataly for nearly four years until late 2019.