Years before he became a controversy-courting media icon, gambling promoter, liquor pitchman and pizza reviewer, David S. Portnoy was drowning in debts.
He owed $59,000 to credit card companies and $18,000 to his father. In one year alone, he had lost $30,000 gambling, court documents show. In January 2004, the 26-year-old filed for bankruptcy protection.
Nearly two decades later, Mr. Portnoy rarely if ever mentions the bankruptcy. Yet he and his company, Barstool Sports, are urging their tens of millions of followers to dive into the fast-growing and lightly regulated world of online sports betting.
After starting out as a four-page newspaper, Barstool evolved into a constellation of sports and entertainment podcasts, blogs and social media accounts with more than 100 million fans. Mr. Portnoy is Barstool’s ringleader, an influencer with nearly 12 million social media followers.
Mr. Portnoy, 45, rose to fame by capitalizing on misogyny and other offensive behavior. He once said that some women “kind of deserve to be raped.” He wouldn’t remove photos showing a toddler’s penis from his blog until police showed up at his door. He made what he acknowledged were racist statements, including using the N-word repeatedly. He outed women who accused him of sexual misconduct, threatened to fire employees engaged in unionizing and repeatedly incited attacks on his critics.
Today, Mr. Portnoy’s reach is greater than ever. The publicly traded casino company Penn Entertainment is poised to take over Barstool, following a 2020 deal in which it bought a 36 percent stake. Mr. Portnoy has been catapulted into the role of public spokesman for the sports-betting industry.
The self-described “degenerate gambler” uses that perch to regale his followers with his betting exploits and cajole them to join him.
From the moment that the Supreme Court opened the door to legalized sports gambling in 2018, businesses and governments have been racing to secure slices of what some analysts predict could be a $240 billion a year market. Companies are shelling out hundreds of millions of dollars on ads and promotions to lure customers. States are vying to offer the lowest tax rates.
Mr. Portnoy’s rapid rise is one of the most vivid manifestations of the frenzy, according to a New York Times investigation based on thousands of pages of court filings, financial documents and communications obtained through open-records requests along with interviews with dozens of current and former Barstool and Penn employees and state regulators.
Instead of flooding the airwaves with advertisements, Penn Entertainment’s play was to slap Barstool’s brand onto a new online sports-betting platform as well as brick-and-mortar casinos. Far from being turned off by Mr. Portnoy’s behavior, Penn executives sought to harness his notoriety to woo a new generation of gamblers.
Regulators, too, have largely looked the other way — a sign of how, with the federal government not overseeing sports betting, states have at times relaxed the scrutiny they previously applied to the gambling industry.
In states like Nevada and New Jersey, gambling regulators have long used painstaking licensing processes to weed out people toting financial or legal baggage such as past bankruptcies, criminal records or gambling problems. Top executives at gambling companies received close attention, but so did those with even peripheral connections to the casinos; some states, for example, required reviews of major shareholders and marketing partners.
Initially, the goal was to keep organized crime at bay. Later, it expanded to combat the appearance of an unscrupulous industry that preys on vulnerable customers.
The mandate for regulators was “not only make sure the games are fair,” said Anthony Cabot, a law professor at the University of Nevada, Las Vegas and an authority on gambling regulation. “They are also there to maintain the public confidence that the gaming industry is not associating with people that they shouldn’t be associating with.”
But with states hustling to attract sports-betting companies and the tax revenue they are expected to generate, some of that oversight has eased.
At least 12 states, for example, allow gambling companies and their affiliates to begin operating on a temporary basis before undergoing full licensing reviews. In other states, regulators have taken relatively narrow views of who should face reviews in the first place.
Penn and Barstool have been beneficiaries. Twelve of the 13 states in which the Barstool Sportsbook operates have not licensed Mr. Portnoy, in part because Penn has argued, and regulators agreed, that he was not involved in running the betting platform. One state, Pennsylvania, granted Mr. Portnoy a license.
The result is that someone who, by dint of his influential position promoting a gambling business, previously would have faced scrutiny by regulators has instead sailed through and become one of the industry’s loudest cheerleaders.
Industry watchdogs say that Mr. Portnoy, perhaps more than anyone else in the United States, is encouraging recklessness among his legions of followers. Most are young men, a group that researchers have found is at especially high risk of problem gambling.
Mr. Portnoy at times mocks the notion of gambling responsibly. He boasts that he typically wagers $25,000 a bet and as much as $500,000. He has encouraged fans to bet their “house, kids, family” on a single game. He has described gambling as “free money” and said it would be “wreckless” to not place a bet.
“David Portnoy pours kerosene on an already flaming situation,” said Brianne Doura-Schawohl, who advises companies on how to promote responsible gambling. “Everything he is promoting, endorsing and speaking to are actually things that could meet the criteria for a gambling addiction.”
Regulators in at least two states have signaled discomfort with Mr. Portnoy.
In Massachusetts, where sports betting is expected to start next year and Penn is awaiting regulatory approval, members of the state’s gambling commission voiced concerns about Mr. Portnoy’s fitness after allegations of sexual misconduct were reported by Insider.
In Nevada, the state’s Gaming Control Board said in a statement to The Times that it is investigating Penn’s compliance with gambling regulations, including its due diligence into Barstool and Mr. Portnoy before their 2020 partnership. Depending on the outcome of the investigation, the board could do nothing or impose penalties, such as forcing Penn to sever ties with Mr. Portnoy.
The Times provided Penn, Barstool and Mr. Portnoy with detailed questions about this article. Penn and Barstool executives did not respond to repeated messages. Mr. Portnoy did not provide answers.
“You have so many factual inaccuracies it’s actually laughable,” he wrote. “It’s below me to even dignify this hatchet job with a response.”
This fall, Mr. Portnoy is touring college campuses, broadcasting his bets in front of cheering students.
One Saturday in late September, Mr. Portnoy was in Knoxville, Tenn., for a University of Tennessee football game. He sat on an outdoor stage with other Barstool personalities and cans of High Noon, a vodka drink that he and Barstool are paid to promote. A raucous crowd of Tennessee fans yelled, cursed and pounded High Noon as Mr. Portnoy shared his latest wager: $100,000 on the University of Georgia to win the college football championship.
The company that would become Penn Entertainment got its start in 1972 as a thoroughbred horse racetrack in Grantville, Pa. Over the years, Penn grew into one of the country’s largest gambling companies, operating more than 40 casinos under the Hollywood, L’Auberge and other brands.
But Penn didn’t have the Las Vegas pizazz of companies like Caesars and MGM. Its focus was on slot machines, and its customers typically were older women. Its growth was slowing. Investors were antsy.
In 2018, the Supreme Court struck down a federal law that blocked sports gambling in most parts of the United States. A frenetic lobbying campaign was soon in motion. Upstart betting companies like FanDuel joined forces with casino giants and professional sports leagues to push states to permit sports gambling. Dozens of states, their officials salivating at the prospect of new tax revenue, rushed to comply.
Jay A. Snowden, the son of a Las Vegas poker dealer, was Penn’s chief operating officer and next in line to become chief executive. He recognized that to position Penn for this new era of digital gambling, the company needed a partner.
“The average age of our casino customers is in the mid-50s,” Mr. Snowden told investors. “How do we solve for that? Sports betting.”
Penn executives spent 15 months exploring deals with gambling and media companies. The talks didn’t get far. Some potential partners were scared off by the prospect of licensing reviews in the 19 states where Penn then operated, Mr. Snowden said.
Then Mr. Snowden met Mr. Portnoy and Barstool.
‘A Legitimate Degenerate’
Mr. Portnoy was a lifelong gambler. When he was 11, his father took him to a racetrack, and the boy was hooked. Mr. Portnoy has said that he placed bets with a Little League coach who happened to be a bookie. At the University of Michigan, Mr. Portnoy started a website called thegamblingman.com to publish his picks.
After graduating, he worked at a market research firm and burned his income on gambling, according to his parents.
“Anybody who thinks that my son is exaggerating his gambling issues, I wish he was,” Mr. Portnoy’s father once said. “Believe me, he is a legitimate degenerate.”
In 2003, Mr. Portnoy left his job and began handing out his self-published Barstool newspaper to Boston commuters. It was geared toward young men. Early advertisers included offshore websites where Mr. Portnoy has said he placed bets. At least one, PartyPoker.com, operated illegally in the United States.
Mr. Portnoy was walking a financial tightrope. He has said that he created fake advertisements in Barstool to spur rival companies to buy their own ads. He wrote under pseudonyms to make Barstool seem like it had a sizable staff. Months after the newspaper’s launch, Mr. Portnoy filed for bankruptcy. The court filing detailed $30,000 in gambling debts.
Barstool started generating buzz in 2004 when Mr. Portnoy put photographs of bikini-clad women on the cover. The newspaper went digital in 2007.
Mr. Portnoy and his colleagues reveled in their rejection of political correctness.
Barstool ran a “Grading the Sex Scandal” column, which ranked the attractiveness of women accused of abusing children. In one typical blog post, Mr. Portnoy wrote of a college student who had appeared in a viral video, “Would somebody for the love of god please stick a dick in this bitch’s mouth and shut her up already.”
Another time, he wrote that Barstool did not “condone rape,” before adding: “However, if a chick passes out, that’s a gray area.” And he repeatedly described Colin Kaepernick, the National Football League quarterback who knelt during the national anthem to protest racial injustice, as a terrorist who resembled Osama bin Laden.
Fueled by Mr. Portnoy’s pugnaciousness, Barstool attracted tens of millions of fans. Mr. Portnoy fondly called them “Stoolies.” They called him “El Presidente.”
In 2016, an investment group led by Peter Chernin, Rupert Murdoch’s longtime second-in-command, invested in Barstool, valuing it at up to $15 million. The high-profile financing accelerated Barstool’s rise. That year, Barstool hired Erika Nardini, a veteran of digital media, as its chief executive. She hosts a podcast called “Token CEO” and in her office displays a poster with the words “Toxic Masculinity.”
Soon Mr. Portnoy used his celebrity to score endorsement deals for products like spiked seltzer and frozen pizzas.
Naming a Price
Around the time that Mr. Snowden and Penn were scouting out partners, Barstool executives were exploring ways to get into sports betting. They talked with gambling companies including DraftKings, but no deals materialized.
“I was stunned,” Mr. Portnoy later said, wondering whether the companies thought he was “too risky.”
In the summer of 2019, a Barstool executive contacted Penn, whose sports-betting business was confined to a smattering of casinos. Rivals had already introduced sports-betting apps.
Mr. Snowden and Mr. Portnoy soon met. They clicked. Mr. Snowden later called Mr. Portnoy and his colleagues “geniuses.”
Here was a way for Penn to reach tens of millions of young, digitally savvy sports fans — a demographic primed for sports betting but less likely to set foot in a casino.
Penn agreed to pay $163 million for a 36 percent stake in Barstool, with the option to buy the company outright. The deal valued Barstool at $450 million — up from barely $15 million four years earlier. The deal included a long-term employment contract for Mr. Portnoy.
Penn planned to use the Barstool name to create a sports-betting app and website, which executives hoped would also offer digital casino games like blackjack. In addition, Penn planned to rebrand sports-betting venues inside its casinos as Barstool Sportsbooks and to open Barstool-branded bars and restaurants.
Barstool agreed to promote the new betting platform and Penn’s casinos to their audiences for up to 40 years.
“He needed us, we needed them, and we named our price,” Mr. Portnoy said later. “There was no negotiation.”
Tax Liens and Public Threats
Over the following months, Penn dug into Barstool’s finances and surveyed the drama that constantly trailed Mr. Portnoy, according to two former executives involved in the deal.
There was plenty to see.
In just the six months after investment talks commenced, but before a deal was announced, Mr. Portnoy said he was retiring from gambling after losing too much money (he was back soon); an $11,795 tax lien was filed against Mr. Portnoy in New York, at least the fourth time he’d faced such a lien; a sex tape featuring Mr. Portnoy leaked; and Barstool reached a settlement with the National Labor Relations Board after Mr. Portnoy threatened to fire employees if they tried to unionize.
Penn’s aming.com/-/media/png/corporate/pngcorporate/pdfs/penn-code-of-business-conduct-11221-final.pdf” rel=”noopener noreferrer” target=”_blank”>code of conduct at the time stated that employees must demonstrate the “highest standards of integrity” and “seek to avoid even the appearance of improper behavior.”
Regulators, too, had a keen interest in avoiding such appearances.
In the 1950s, authorities in Nevada, which had become a popular destination for the mafia after the legalization of gambling two decades earlier, adopted rules — such as requiring people to complete financial questionnaires — to fend off organized crime.
Over time, as other states legalized different types of gambling, the rules evolved to also encourage social responsibility and ensure public trust. Prospective casino operators often had to provide regulators with their tax returns, credit card statements, computer hard drives and mobile phones. Some regulators even insisted that people explain their tattoos and scars or grilled them on having hired undocumented immigrants as nannies.
Gambling licenses were considered a privilege. The burden was on applicants to prove they were of good character, honesty and integrity.
Those affiliated with or connected to gambling businesses — including major investors, vendors and marketing partners — also could face regulatory reviews, even if they didn’t need to be officially licensed.
One result was that casino companies rushed to cut ties with celebrities after even a whiff of controversy, fearful of upsetting regulators. Caesars ended its relationship with the chef Paula Deen in 2013 after she admitted to using the N-word. Las Vegas Sands closed Mario Batali restaurants in 2018 after women accused him of sexual misconduct.
State gambling regulators “generally have broad discretion to control or eliminate behaviors that are deemed to portray regulated gaming in a bad light,” said Richard Schuetz, who spent decades as a gambling executive and regulator in California.
Times, however, soon changed. Egged on by industry lobbyists, lawmakers and governors competed to get sports gambling up and running as quickly as possible. Some regulators wanted to be seen as the industry’s partners, not their policemen.
Before finalizing the Barstool deal, Penn told state regulators about the pending announcement. They discussed whether Mr. Portnoy and others at Barstool would need to obtain gambling licenses, according to the two executives.
Those conversations with regulators convinced Penn executives that as long as they controlled the gambling operations and kept Barstool employees in marketing roles, Mr. Portnoy and his colleagues wouldn’t face state licensing reviews, said Timothy J. Wilmott, Penn’s chief executive at the time.
“We certainly knew Barstool was edgy and that they had content out there that appealed to their audience, but we didn’t feel at the time that there was anything there that we could not manage,” Mr. Wilmott said in an interview.
Penn later lobbied officials in Arizona to limit licensing requirements to employees who have “the highest decision-making authority within an organization,” according to an email reviewed by The Times. That would mean that employees like Mr. Portnoy probably wouldn’t come under regulators’ gaze. Penn warned that more stringent requirements would needlessly slow down the rollout of sports betting in Arizona — and therefore delay the expected gusher of new gambling tax revenue.
Sports betting went live in Arizona months later, with regulators opting to grant licenses to entities, not individuals. Penn got a license for its Barstool app; Mr. Portnoy wasn’t scrutinized.
Regulators in other states applauded Penn’s deal with Barstool before it was made public.
“I’m excited for Penn and for Barstool,” Ronnie Jones, then the chairman of the Louisiana Gaming Control Board, wrote to Ms. Nardini, the Barstool chief executive. “I think this is a great partnership.” (The Times obtained the email via a public records request.) Louisiana permitted Penn to offer sports betting under the Barstool brand and didn’t require Mr. Portnoy to be licensed.
In an interview, Mr. Jones, who is no longer on the oversight board, said that he wasn’t familiar with Barstool at the time. “When the name Barstool first came up, most of my life experience had been with the piece of furniture,” he said.
It is not clear whether Penn told regulators about Mr. Portnoy’s bankruptcy and gambling losses, which experts said licensing authorities traditionally would have scrutinized.
Mr. Schuetz, the former regulator, said he was surprised that state regulators would conclude that Mr. Portnoy’s “questionable behaviors are consistent with a suitable means of operation in modern gaming regulation. In my 50-plus years in the industry, this is a very significant change.”
Penn and Barstool unveiled their deal on Jan. 29, 2020. Mr. Portnoy received tens of millions of dollars in cash and shares of Penn; he has said he’s worth about $100 million. And he was elevated into an elite position in the world of sports betting.
“This is kind of what I always wanted to do with my life, to be honest,” Mr. Portnoy said on a conference call with investors that day. “I wanted to be involved in shaping, kind of, the gambling industry.”
‘Come Bet WITH US’
When Penn’s Barstool betting app went live in Pennsylvania in September 2020, Mr. Portnoy made good on his promise to push it to his followers. “We’ve bet WITH YOU for the past 17 years,” exhorted a video that he posted on Twitter. “Now come bet WITH US.”
Across its network of websites and social media accounts, Barstool promoted the gambling app. It also broadcast pregame shows and other videos in which Mr. Portnoy and others watched sports and discussed their wagers. Fans were encouraged to use the Barstool betting app to gamble alongside or against Mr. Portnoy and his Barstool colleagues.
Regulators in 13 states have permitted Penn to offer Barstool-branded sports betting, with four states also allowing digital casino games. Penn also has introduced Barstool bars and sports-betting venues in 12 locations.
The results for Penn have been mixed. The Barstool betting app is the seventh-largest in the country by revenue, according to research firm Eilers & Krejcik Gaming. It commands about 3 percent of the sports-betting market, less than half of what analysts had projected.
Penn, which has said it will exercise its option to buy Barstool outright in February, remains committed. The new Barstool Sportsbooks inside Penn’s casinos have enticed younger gamblers to visit. Once inside, Penn executives say, they spend money on gambling, food and beverages — and often return.
Thanks at least in part to the Barstool deal, customers who are between 21 and 44 years old now account for about 20 percent of Penn’s revenue — a figure that nearly doubled over the past few years, Mr. Snowden told analysts this month. He said Barstool and Mr. Portnoy have proven to be “amazing partners for us.”
They have also at times engaged in what critics describe as problematic behavior, including ridiculing the concept of responsible gambling and trumpeting his five- and six-figure bets.
In a September 2021 Twitter post, for instance, Mr. Portnoy said, “First. Always bet responsibly. 2nd. Here is how you win a quick ¼ million,” alongside a photo of a bet slip showing a $19,000 wager he placed on the Barstool app.
Later that month, Barstool and Penn agreed to pay a total of $17,500 to Indiana regulators after Barstool posted a TikTok video in which a young woman minimized the consequences of losing money. The video violated Indiana’s laws governing deceptive marketing of gambling. (Penn, realizing the video was inappropriate, flagged it to regulators in multiple states, but only Indiana appears to have taken disciplinary action.)
Keith Whyte, executive director of the National Council on Problem Gambling, said that Mr. Portnoy and Barstool routinely distort the risks of gambling. “He is normalizing sports betting in ways that frankly often come off as irresponsible,” Mr. Whyte said.
Circling the Wagons
On a Thursday morning in November 2021, an email arrived in the inboxes of gambling regulators across the country. The subject line: “Confidential — David Portnoy Article.”
Insider had just published an article detailing allegations from women who said they’d had sexual encounters with Mr. Portnoy that turned violent. Mr. Portnoy denied the claims and sued for defamation. (The suit was dismissed.)
“We wanted to reach out to let you know that we have seen the article, understand the serious nature of these allegations, and are reviewing it carefully,” Chris Soriano, Penn’s chief compliance officer, wrote in an email to regulators reviewed by The Times.
Penn had reason to be worried.
Three years earlier, sexual misconduct allegations against the casino magnate Steve Wynn prompted his departure from Wynn Resorts and led regulators in Nevada and Massachusetts to impose tens of millions of dollars in penalties.
Now many state regulators either looked past or ignored the accusations against Mr. Portnoy.
Some regulators privately expressed concerns. In Illinois, for example, the gambling board’s assistant general counsel wrote to colleagues that Mr. Portnoy was “a creep who has questionable sexual encounters with much younger” women. In Indiana, the head of the gambling commission told Mr. Soriano that regulators viewed the allegations “as very serious, requiring prompt communication regarding Penn’s planned course of action.”
Yet there is no sign that Illinois, Indiana or other states took disciplinary actions.
Executives at Penn and Barstool, meanwhile, circled the wagons.
Ms. Nardini said on her podcast that the company was taking the situation “incredibly seriously.” Then she added: “Dave Portnoy is the most honest, forthright person I have ever met.”
The next day, Mr. Snowden, who had become Penn’s chief executive in 2020, held a videoconference call for employees. He criticized the Insider article and defended Mr. Portnoy. Mr. Snowden was wearing a Barstool sweatshirt.
Even as Penn executives defended Mr. Portnoy, the company acknowledged the perils of being associated with him.
The list of “risk factors” that Penn discloses to investors includes the following warning: “Our relationships with state gaming regulators, stakeholders and business partners could be adversely affected as a result of our affiliation with Barstool Sports.”
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