When biotech entrepreneur Dr. Greg Bailey was weighing where to put his money two years ago, he had options that most people could only dream of. Premier League football clubs were on the table, as were stakes in iconic American franchises like the New York Yankees and the Milwaukee Bucks. But Bailey, who had walked away with a fortune after Pfizer acquired his cancer medication company Medivation for $14.3 billion in 2016, kept coming back to the same basic question: what was actually going to make him richer? The answer, surprisingly, was not English football.
“I want something that will appreciate or make money, which eliminated, in my mind, most of the Premier League football teams,” Bailey told The Athletic. Instead, he bought the franchise for the Canadian team in SailGP, the fast-growing international sailing league that has drawn comparisons to Formula 1 on water. At the time, it was a relatively obscure property. Since then, however, a wave of celebrity investors has flooded into the league, including World Cup winner Kylian Mbappé and Hollywood stars like Ryan Reynolds, Anne Hathaway, and Hugh Jackman. Bailey had barely any background in sailing — just some youthful windsurfing — but neither do most of the famous names now piling in.
Bailey’s path to sports ownership was never part of any childhood plan. Raised by a single mother in the Toronto suburb of Don Mills, he started his career as an emergency room doctor before building a string of successful biotech ventures. It was only after his first major exit that the calls started coming, offering him slices of storied teams at eye-watering valuations. A second sale last year only intensified the frenzy. “It was just like agents calling on steroids,” he said. What drew him to SailGP was a combination of financial discipline — including a $10 million annual cost cap designed to prevent the wealthiest teams from simply buying championships — and the kind of exclusive access that traditional sports rarely offer. Owners can ride on the boats, meet the crews, and entertain high-net-worth guests in the league’s Adrenaline Lounge suite, where average income reportedly tops $330,000.
Not everything has been smooth sailing. Bailey is candid about his frustrations with venues that lack reliable wind, such as Lake Geneva, Dubai, and Abu Dhabi, where the high-tech F50 catamarans sometimes struggle to reach even 15 miles per hour compared to speeds exceeding 60 mph when conditions are right. Media growth has also been slower than he anticipated, though he says he is getting a crash course in how younger audiences consume sport through bite-sized clips on YouTube and TikTok rather than traditional television broadcasts. Still, there have been moments that reminded him why he took the leap. When SailGP visited Halifax last month, the Nova Scotia capital embraced the event with a passion that caught him off guard and left him genuinely moved. For a man who insists every investment must pass a cold-eyed financial test, that flicker of emotion may prove to be the most valuable return of all.