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Barstool Founder Dave Portnoy as we look at the details of the sports betting media partnership between Barstool Sports and DraftKings
Barstool Founder Dave Portnoy and Guy Fieri look on in the first quarter during Game 3 of the 2022 NBA Finals. Photo by Maddie Meyer/Getty Images/AFP.

A rumored partnership between Barstool Sports and DraftKings — one of our best sports betting sites — has come to fruition, according to a social media post from Barstool CEO and Founder Dave Portnoy Sunday night.

After losing its prior market partner when Penn Entertainment all but cast the Barstool brand aside in favor of ESPN BET, Portnoy's sports betting baby appears to have landed on its feet with an important tie-up with U.S. legal sports betting heavyweight DraftKings.

According to Portnoy, “We are back in the gambling business. We just formed a partnership with DraftKings. We’re back where we started. Big, huge deal. I don’t have the numbers, lot of zeroes, maybe the biggest deal in the gambling space with a partner. I don’t know.”

Timing was everything

Unfortunately for Barstool Sportsbook, the deal with DraftKings could not have commenced until the end of the Super Bowl. Hence the late Sunday announcement of the deal after the final whistle in the 2023-2024 NFL season by Dave Portnoy.

Barstool was subject to a non-compete order following its PENN breakup, in which it was prohibited from operating in the U.S. market for a set amount of time. The non-compete ended right after the NFL's Championship game.

While it is not ideal that Barstool was not active for the most active sports betting day on the U.S. calendar, March Madness, the second biggest sporting event on American soil, is just around the corner. DraftKings, which has been gaining ground on FanDuel as the most popular sportsbook in America, will likely get a boost in time for the annual NCAA Basketball tournament. Bettors can take advantage of what DraftKings has to offer by using our DraftKings promo code.

Portnoy the big winner

Despite losing his affiliation with Penn Entertainment last summer, Barstool CEO and Founder Dave Portnoy looks like the big winner in the newly announced partnership with DraftKings.

Portnoy originally sold the Barstool brand to Penn for $500 million, only for Penn to give up on it and sell it back to Portnoy for $1 once the Penn/ESPN BET partnership was consummated.

While no financial details of its DraftKings partnership have been announced, the multi-year deal is expected to be lucrative, with Portnoy personally benefitting financially and his millions of stoolies getting back in the betting game.

Starting with a "Free Throw Challenge"

On Monday at 5 p.m. ET, Barstool Sports will mark its return to the legal sports betting realm and its new partnership with a free-to-play "Free Throw Challenge" that will award $100K in prizes. The announcement came on social media.

It is a contest at the Barstool offices with Barstool employees gathering, forming teams, and trying to sink 41 consecutive free throws. The contest will be streamed, and questions will be asked of viewers about the content of the contest.

Viewers who are able to answer the most questions during the streamed event will split $100K in prizes.