David Portnoy

 Portnoy left Portnoy quit the Yankee Group after four years and founded Barstool Sports in 2003. It was a four-page sports newspaper that Portnoy published in the streets and subway stations of Boston. The newspaper was created to appeal to men of the era and averts the pitfalls of the notion of political right-wing slants. The first advertisers for the newspaper were betting websites that operated offshore, such as PartyPoker.com. The website was operating illegally within the United States. Portnoy was the newspaper's first 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" who is a blunt and candid character. Portnoy's writing was well-received by the younger generation of men. The paper became an integral part of the bro-culture. In 2010 Portnoy joked about female raped women, declaring that if you're 6 feet tall and wearing skinny jeans, you are probably destined to be sexually assaulted. Portnoy joked about female rape victims in 2016, when he used the word "N-word" to describe the content of a Barstool video. The video was later revealed that the Barstool headquarters were relocated to New York City. Penn National Gaming purchased 36% of Barstool Sports from its founders in 2020 for $163 million, that included $135 million in cash and $28 million in Penn preferred stock that is non-voting. The Chernin Group retained a 36% stake in the business. Portnoy, who continues to oversee the site and retains the creative control, holds the remaining 36 percent.