The Book Review of David McKee on the Life Story of Dave Portnoy, Who Climbed the Throne: A Portrayal of How the Jester Became a Monarch, Titled "How the Jester Became King: A Biography of Dave Portnoy"
By David McKee
"The public buys the dream they never thought possible." - A man from the movie Once Upon a Time in the West. Perhaps this sentiment rings true for Dave Portnoy, the founder of Barstool Sports, who turned the rags-to-riches story into his reality, proving that sometimes, dreams do come true - even at a dollar's price. McKee's latest biography, Fools Rush In: How a Rebel Became the King, takes us on Portnoy's astonishing journey, one that simultaneously charms and confronts.
Forty captivating chapters and more than 370 pages delve into the tale of Portnoy, the ultimate underdog, charting his life from the quaint town of Massachusetts in 2003, where he started with $25,000 borrowed from his father, a successful lawyer, to build his sports-focused newspaper empire. Scrambling day and night, Portnoy's dogged determination transformed his turbulent dream into a digital kingdom, expanding to become a blogging, podcasting, and talk radio behemoth. (The universe, however, just couldn't seem to give him a TV break.)
Driven by innate business acumen, a perennial sense of injustice, and the occasional stroke of luck, Portnoy transformed his Bostonian chip into an incredibly valuable currency. His business ventures, initially including sports bars, apparel, and even pizzas, sold at Walmart, made his Barstool brand a household name.
Born harboring resentment, in 1977, Portnoy confessed later, "I've been a compulsive degenerate gambler my entire life." His resources, media assets, and influence grew exponentially, mirroring his gambling wins and losses. It was as if he turned his media empire into a protective racket, declaring, "If you don't play ball, be prepared to get bashed." Again, this was not just mere talk; evidence can be found in NFL Commissioner Roger Goodell's experiences.
From the get-go, Barstool Sports brashly embraced sexism, featuring pictures of women in scant clothing – often without their permission. Portnoy's personal beliefs on the subject can be found on page 59, where he candidly shares, "Alas, bottom line is that chicks that aren't prepared to be sexually assaulted just a little bit shouldn't go on pub crawls to begin with."
Portnoy reveled in his role as the unfiltered provocateur, eagerly courting controversy at every turn. Stirring trouble on campuses, in the media, and on the internet, he thrived on being the mischievous catalyst. The result? An unstoppable following hungry for the edgy, unfiltered authenticity that is known as Portnoy's trademark.
A Rebel with a Purpose
McKee brilliantly describes how Portnoy identified the niche market of privileged white male humour, cornering the market like no one before him. His disdain for the oppressed, the vulnerable, and the marginalized was a theme that came into stark relief as he spewed vile verbal attacks on individuals he deemed beneath his notice.
At least he was generous during the COVID pandemic, donating funds to charitable causes. However, this altruism seemed more the exception than the rule, making one question the motivations behind such acts of goodwill.
Fortune favored Portnoy's transgressions, even when his own excesses threatened to derail his success story. Take the infamous Barstool Blackout Tour, which began as a series of disastrous drinking parties but evolved into a valuable marketing endeavor.
Despite his renowned insensitivity, Portnoy managed to cultivate an almost cult-like loyalty among his employees, fondly referred to as "Stoolies." The sheer absurdity of working under unfavorable conditions created a bizarre sense of rapport, as if the Stockholm Syndrome had set in.
Alpha Males Reign
Portnoy espoused the concept of "take what you want" as one of his mottos, mirroring the rise of a disturbing trend in modern society: the cult of selfishness. Portnoy's conduct did not create this predicament, but he certainly took advantage of it to the hilt.
Peter Chernin, the founder of Hulu, saw incredible potential in Barstool, recognizing its online sports betting potential. He acquired it in 2016 for $12.5 million, jumping on the barstool bandwagon as The Chernin Group teamed up with Portnoy to make Barstool the ideal blend of humor, sexism, and sports betting for the digital age.
The collaboration between Portnoy and Chernin culminated in a valuation of $100 million for Barstool. To be sure, polished content and harmonious aesthetics were never hits with the Stoolies, who eagerly consumed the raw, unfiltered entertainment offered by Portnoy and his gang of sidekicks.
Erika Nardini's arrival as CEO in 2018 marked a turning point for Barstool, with online visits soaring from eight million per month (in 2017) to a staggering 66 million just three years later. Her ruthless business acumen and ability to monetize the Barstool brand efficiently helped solidify its position in the market.
Love, Sportsbook, and Other Curses
Hulu wasn't the only company to see value in Barstool. In May 2020, Penn Entertainment, led by Jeff Snowden, a former Harvard quarterback, purchased Barstool for a whopping $450 million. This eye-watering deal, valued at 4.5 times its worth under The Chernin Group, raised eyebrows in the industry.
Snowden banked on Barstool being a powerful marketing tool and mouthpiece for Penn's brand. However, his new acquisition brought its own set of challenges, with Portnoy's racially charged comments causing PR headaches for Penn. This, of course, did not stop Snowden from dressing up in Barstool gear at the office or underwriting a Chicago office for the company to the tune of $20 million.
The two seemed inexplicably entwined, with Snowden bafflingly eager for Portnoy's approval. The result was a partnership that appealed to many, but not without its share of pitfalls. Penn's sportsbook applications, despite Snowden's best efforts, never managed to crack the top five in the market, suffering from a dismal 3% share. In addition, Portnoy's reckless statements about sports betting threatened to derail Penn's regulatory compliance and stymie its progress.
Finally, in May 2023, the relationship came undone. Portnoy launched an unprovoked tirade against Penn on his podcast, causing a massive sell-off of stocks that obliterated $633 million from Penn's market capitalization in a single day. Frosty shoulder shook hands with cold reality as Penn cut ties with Barstool, severing a relationship with stunning consequences for both parties – consequences worth every penny, one would say, for Portnoy, who left Penn richer and even more respected than when he started.
- Psychologists may find Dave Portnoy's lifetime of compulsive gambling a fascinating case study, as his media empire's valuation mirrored his gambling wins and losses.
- In the world of entertainment, celebrities like Peter Chernin have seen potential in Barstool Sports, not only for its sports betting offerings but also for its provoking, edgy content.
- casino and sports betting have become integral parts of Barstool Sports, with its collaboration with Penn Entertainment providing a significant boost to its value, despite the occasional PR challenges.
- Books such as David McKee's biography on Portnoy offer insights into his life, including his controversial views on sexism and his turbulent relationship with Penn Entertainment.
- Portnoy's fame and influence have grown largely due to his role as a provocateur in the entertainment sphere, with many following him for his unfiltered, sometimes offensive, approach to topics such as sports, gambling, and politics.
