Title Examining the Life Story of Barstool Sports Founder, Dave Portnoy: A Deep Analysis
Unvarnished Account of Dave Portnoy's Unpredictable Journey to the Top
By David McKee
"Better to be a pirate than to join the navy." - Steve Jobs
In Dave Portnoy's case, the expulsion from his corporate navy led him to the uncharted seas of online media and the kingdom he calls Barstool Sports. Knocked down and betrayed by the establishment, Portnoy didn't just reinvent himself. He made a mockery of it. So, peek into the pages of Charlie Stanton's new biography, How the Jester Became King (Post Hill Press), to find out what america truly loves: the unexpected, the audacious, the rebel with a cause.
Dive into the rough-and-tumble story of the David versus Goliath saga that spans more than two decades, and explore the rise of a man who started with a borrowed loan of $25,000 and ended up having his Barstool Sports empire sold back to him for a measly buck. Sounds too good to be true? Keep reading to find out how it's all part of the underdog charm.
The book, meticulously researched and compellingly written, chronicles Portnoy's zany escapades, his unapologetic brashness, and the sheer ambition that catapulted his brand to the top tiers of the media world. Forty chapters and 374 pages later, the overarching lesson learned is that fish definitely stink from the head down.
Born with a chip on his shoulder in 1977, Portnoy became a degenerate gambler early on, readily confessing to his self-proclaimed addiction[2]. It's no surprise then, that he'd employ his media assets like a protection racket, often going toe-to-toe with industry titans, cracking jokes about the NFL Commissioner Roger Goodell, and flaunting his business acumen as an audacious stunt double for Ike Turner.
Portnoy's Barstool empire, spawned from a sports-talk newspaper, metastasized into a digital empire that includes blogging, podcasting, sports bars, apparel, and even a line of pizzas. With an undeniable business vision, a bottomless sense of grievance, and a penchant for luck, Portnoy turned his massive chip into a money-making machine.
The book stands out with its no-holds-barred approach, delving into Portnoy's sexist persona that prominently features photos of scantily clad women on Barstool Sports[3]. Besides, one doesn't have to dig deep to find unprintable comments about female reporters[3].
Similar to the boy who cried wolf, Portnoy relished his role as the irresponsible provocateur, stirring the pot on university campuses and inciting riots, often with shock jock tactics that employed half-truths, twisted facts, and sheer defiance of established norms.
Despite the controversy, Portnoy's antics found favor with millions, cornering the market on white privileged male humor[4]. Early success enabled him to dabble in philanthropy during the covid-19 pandemic, but such excursions were largely out of character.
Behind the scenes, however, lay a worker bee with unparalleled tenacity, tirelessly pushing papers around the clock and pushing the boundaries of workplace decorum with a managerial approach that bordered on abuse. His systematic exploitation of his followers and underlings created a Stockholm Syndrome-like sense of loyalty among the inner core of "Stoolies."
Here's the kicker: Portnoy's questionable business practices earned him a hefty $450 million deal with casino operator Penn Entertainment[2]. But his racism and blatant sexism didn't just stir up public relations headaches. It also opened the door to a friendship with Donald Trump and right-wing media.
Hulu founder Peter Chernin saw the value in Barstool, buying it in 2016 for $12.5 million[4]. However, Chernin's cooperation set the stage for Portnoy's eventual exit, selling the company back to him for a mere dollar[5].
The once-in-a-lifetime story does come with a caveat: Portnoy's style of leadership, questionable business practices, and slew of scandals have left a trail of broken relationships and damaged reputations. The infamous sex tape scandal and the resurfacing of his sexually abusive past send Penn Entertainment shares plummeting[5].
Sultan of Squandered Opportunities
What is it about Portnoy that inspires such loyalty and yet fuels such ire? Perhaps it's the self-made man in a materialistic world, a testament to the power of determination and grit. Or maybe people look up to him because deep down they want to say or do the things he dares to do, without censoring themselves.
Whatever the reason, Portnoy's brand power continues to grow. Though his empire seems to have plateaued, he remains a symbol of irreverence and nonconformity. In 2023, he made an arrangement to be an advertising partner of DraftKings, keeping a safe distance from his troublesome past[5].
Written in a breezy, engaging style, How the Jester Became King offers a raw and candid look into the life of an opinionated influencer with questionable morals, but one who undeniably captured the hearts and minds of millions of followers. It's a book that's hard to put down, a rambunctious ride through the enigmatic life of Dave Portnoy.
**** This exclusive book review was originally published in Casino Life Magazine Issue August 2025****
**Enrichment Data**
- Dave Portnoy (born 1977) is an American entrepreneur and media personality who founded Barstool Sports. The biography, How the Jester Became King (Post Hill Press), by journalist Charlie Stanton chronicles Portnoy's rise from his Massachusetts roots to heading the Barstool Sports empire. Initially starting with a sports-talk newspaper in 2003, Portnoy expanded his media footprint into digital media through blogging, podcasting, sports bars, apparel, and even a line of pizzas. He courted controversy through his sexist persona, often featuring scantily clad women on Barstool Sports[1].
- Portnoy's success came with a price, as fans and critics alike debated the ethics and coarseness of his behavior[2]. In 2016, he sold Barstool Sports to Hulu founder Peter Chernin for $12.5 million[4]. Chernin later sold the company back to Portnoy in 2023 for $1[5].
- The controversy surrounding Portnoy is not limited to his focus on women, as he often made sexist and unprintable comments about female reporters[3]. He has also been embroiled in sex scandals, including the infamous sex tape scandal, which sent Penn Entertainment shares plummeting[5].
- Despite the controversies, Portnoy's brand appealed to millions and continued to grow[4]. In August 2023, he made an arrangement to be an advertising partner of DraftKings[5].
- Portnoy's abrasive leadership style and questionable business practices burned bridges and left a trail of broken relationships and damaged reputations in his wake[5]. At the height of his fame, an unflattering documentary, Barstool Presents: Dave Portnoy, aired on HBO in 2021[5]. The documentary shined a light on his damaging business practices, particularly towards his employees[6].
- Dave Portnoy's empire, originally a sports-talk newspaper, expanded to include casino-related ventures, such as partnering with DraftKings in 2023, reflecting his interest in both sports and gambling.
- Throughout the journey chronicled in the biography How the Jester Became King (Post Hill Press), Portnoy's media brand, Barstool Sports, also delved into the world of entertainment, showcasing celebrities and their scandals, maintaining a connection with the entertainment industry.
