Jay Z The Gambler

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These days it’s not uncommon to hear celebrity entertainers, from actors to athletes, talking about their individual “brands.” As the iconic status of these celebrities grows, the money-making opportunities inspire many of them to seek side streams of revenue that often amount to entire careers in business, marketing, and even other avenues of entertainment. And for some, this journey is extremely interesting. Take, for example, Jay Z.

Widely recognized as one of the best hip-hop artists ever, Jay continues to make best-selling music. However, he’s also focused more and more in recent years on his personal brand outside of the rap game. And when it comes to Hov, that brand involves no shortage of gambles.

The latest example for Jay Z is in his journey into sports agency. A few years ago, the rapper famously sold his share of the New Jersey Nets (despite having helped move the team to Brooklyn) in order to pursue interests as a sports agent. One of his first moves thereafter was signing then-Yankees star Robinson Cano and pricing the New York Yankees out of the bidding. Once upon a time that sentence would have appeared to not make sense. But when Jay Z slapped a 10-year, $300 million-plus price tag on the player who was at the time his only major signee, even the Yankees (incidentally, his favorite team) balked at writing a check.

Depending on the report you believe, this was a $50 to $100 million gamble that some team out there would pay Cano that much more than the Yankees were willing to. Whether it paid off or not is debatable. Cano got his 10-year deal from the Mariners, for $240 million, which was more than the Yankees offered total, but less per season.

According to a Forbes report of this whole process, it wasn’t Jay’s first big gamble either, but rather an example of a known aspect of his personality. Interviewed in the article, Fab 5 Freddy says that Jay used to talk frequently about the game “Guts,” and said of the rapper’s interests, “I think there’s a connection between that and business. It’s all a gamble.” And with Jay, it turns out that interest in gambling has extended past his early days in hip-hop, connecting an old interest across his career and to his agency days.

The truth is, the rise of online gaming has helped to rope in a great deal of celebrity interest over the years. The boom began in 1996 when InterCasino became the first major online casino, ultimately offering arcade versions of table games and slots—you can sample the latter here—to allow players the flexibility to play these games online. This sort of easy leisure and real money gambling opportunity apparently appealed to a number of celebrities with expendable income, and now the list of celebrity poker players (who practice and play the game online at a number of established sites) is too long to count.

Jay Z, of course, is part of that list, and he has taken his interest in gambling activity to some serious high stakes environments. According to Gambling Beat, he even suffered a $500,000 loss at the Las Vegas poker tables back in 2008. Not quite a $100 million baseball gamble, but it may have been a preview of things to come!

Through it all, one thing seems clear: Jay Z is about as likely to make a high-profile business gamble as he is to release more music, which is to say it’s a virtual guarantee. It’ll be interesting to see where he takes his hobbies next.

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