David Portnoy

 Portnoy left Portnoy quit the Yankee Group after four years and launched Barstool Sports in 2003. The paper was a sports-themed four-page paper that Portnoy distributed on the streets and subway stations of Boston. This newspaper was designed to appeal to young men and was adamant about avoiding political right-wing slants. Early advertisers in the newspaper included offshore betting websites such as PartyPoker.com which was operating in the United States illegally. Portnoy was the first newspaper's writer. But he later included other freelance writers to the newspaper, including Todd McShay. In 2007, Barstool Sports began to create blogs. Portnoy developed his reputation as "El Presidente" which is a blunt and candid character. Portnoy's writing was well received by young men. The paper became an integral part of the bro-culture. In 2010 Portnoy made a joke about women being raped declaring that if you're 6 feet tall and wear skinny jeans you probably deserve to be assaulted. In 2016, Portnoy used the N-word in an Barstool video, which he later apologized for.Peter Chernin's The Chernin Group purchased a majority stake in Barstool on January 7, 2016 and was later stated that the headquarters would relocate to New York City. Penn National Gaming acquired 36% of Barstool Sports from its founders in 2020 for $163 million, that included $135 million in cash and $28,000,000 of Penn preferred stock that is non-voting. The Chernin Group retained a 36% share of the business. Portnoy, who continues to manage the site and maintains control of the site's creative direction, keeps the remaining 36%.