This month, two events highlighted the outsize ambitions of Michael Rubin, the billionaire Fanatics C.E.O. who has reshaped the sports landscape through high-profile dealmaking. The first, of course, was Rubin’s annual all-white party over the Fourth of July weekend, held at his $50 million Hamptons oceanfront home. The celebrity guest list included the Kardashians, Tom Brady, Drake, Robert Kraft, and Leonardo DiCaprio, each of whom dutifully donned colorless outfits and left with a brand-new pair of custom Air Jordan 1s. Rubin, never one to miss an opportunity to promote himself,  then posted multiple videos of the whole affair on his Instagram.

The second, more subdued event took place Monday in a Boston courtroom, where questions surrounding Rubin’s recruitment of the head of Fanatics’ L.A. office, Michael Hermalyn, were being adjudicated before the 1st U.S. Circuit Court of Appeals. The case is tied to a January dinner at Rubin’s New York City apartment, when he approached Hermalyn, a former CBS executive charged with handling V.I.P. partnerships at DraftKings, about spearheading a new Fanatics division aimed at cultivating celebrities and influencers. A few days later, the two men reconvened in Pennsylvania, and Hermalyn agreed to come aboard, pending the resolution of some final issues.