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Investigation Surfaces Following Dave Portnoy’s Tweets About Jose Canseco Taking A Dive

Barstool Sports deserves all the credit in the world for its efforts to raise money for small businesses that have been crushed by the coronavirus pandemic. As of the morning of February 15, The Barstool Fund has raised more than $35 million and supported 258 businesses.

The edgy company with its provocative president, Dave Portnoy, is not afraid to push the envelope on almost any issue. Sometimes, it is for the good of society and, at other times, the words uttered by Portnoy have the potential to put his own company at risk. A case in point concerns recent developments surrounding Barstool Sports’ Rough N’ Rowdy (RnR) event that took place in early February and featured a fight between former Major League Baseball player Jose Canseco and Barstool Sports’ intern Billy Football.

The fight lasted 10 seconds. People who paid to watch the event may have been upset that it was a very short-lived form of entertainment, but that is not the concern now, a couple of weeks after the fight. Instead, the issue is whether Canseco took a dive, which is exactly what Portnoy tweeted after the match.

“Jose [Canseco] 100% took a dive. We paid half up front and he got double if he won,” Portnoy tweeted. “We thought that would ensure he’d fight. We were wrong.”

He added, “Jose [Canseco] didn’t fight. He laid down in 5 seconds. We will now add a morality clause in future contracts[.]”

The lasting concern is that people actually bet on the outcome of the fight. While Barstool Sportsbook took the proper approach in voiding all bets that were placed on Canseco to prevail, that does not mean that the company is necessarily out of the woods on this issue.

According to PlayMichigan, a governing body in West Virginia is investigating the event that featured Canseco’s fight. That governing body, the State Athletic Commission, sanctioned the event and has reportedly not committed to sanctioning any future Rough N’ Rowdy cards.

Portnoy would be wise to exercise caution in the future when tweeting about the circumstances surrounding events that his company promotes and also accepts wagers on. His company is so completely involved in all aspects of the event that what seems like harmless commentary in the form of calling out Canseco for “taking a dive” can become a real concern in the legal, regulated sports betting space.

Taking all of the above into consideration, I am definitely hoping for a future Rough N’ Rowdy event featuring a fight between Barstool Sports’ PFT Commenter and The Action Network’s Darren Rovell.


Darren Heitner is the founder of Heitner Legal. He is the author of How to Play the Game: What Every Sports Attorney Needs to Know, published by the American Bar Association, and is an adjunct professor at the University of Florida Levin College of Law. You can reach him by email at heitner@gmail.com and follow him on Twitter at @DarrenHeitner.