Feared dealmaker plots his next move

2 min read

Michael Rubin discovered a talent for wheeling and dealing as a teenager and now sits on a $31bn sports merchandising empire. He has his eye on new opportunities. Jane Lewis reports

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Billionaire Michael Rubin is best known outside the business world for hosting an annual July Fourth party at his $50m estate in the Hamptons, with a celebrity guest list that has made it the hottest event of the summer. Last year, Vanity Fair dubbed him “this generation’s Gatsby”.

Much of the mystique surrounding the fictional Jay Gatsby relates to the unknown origins of his fortune – author F. Scott Fitzgerald hinted it came from illegal activities such as bootlegging during Prohibition. No such mystery surrounds Rubin, 51, whose privately held sports merchandising empire, Fanatics, is now valued at roughly $31bn, says Bloomberg Businessweek. Nonetheless, this “aggressive entrepreneur” has been dubbed “the most feared dealmaker of his generation”.

With good reason. Rubin’s path to huge wealth has been studded with “hijacked” contracts, “scuttled” public offerings and “stealth acquisitions”. Thwarted opponents include Michael Eisner, the former Disney boss who was himself considered “one of the most feared executives ever to enter a boardroom”. Given Rubin’s reputation, it’s little wonder rappers such as Drake, Meek and Lil Baby consider him their “favourite billionaire”, says Vanity Fair.

In the years since they met, Rubin has come to see former jailbird Lil Baby as a brother. “I always say if I grew up how he grew up, I would have been the biggest drug dealer on the planet.”

His own background was rather more cushioned. Born in 1972 and raised in Lafayette Hill, Pennsylvania, young Mike “took to making money at an early age”, noted Forbes in 2006. As an enterprising 13-year-old with a love of skiing, he “transformed his parents’ home into a shop for tuning skis” and was soon selling gear out of the basement on a consignment basis for retailers looking to offload merchandise.

Rubin swiftly graduated to opening his own ski shop. By the age of 16, he was some $120,000 in debt but, thanks to some clever wheeler-dealing, grew the business into five shops by the time most kids were going to college. When the 1990s internet boom struck, he was “ready with a business model”. His venture, GSI Comme