On February 11, the “inventor” of Barstool Sports, Dave “El Presidente” Portnoy, used his social media to make the big announcement regarding the new multi-million-dollar partnership that his company and DraftKings have agreed upon.  

Portnoy, who is also the owner of #DDTG Global and a “Brick Watch Man” and “2-time bee sting survivor” as he describes himself on his X (former Twitter) account, officially confirmed that the two companies have completed the multi-year sports betting media partnership, a deal that was initially reported by Sportico in January. 

His X message said “We’re back to our roots. DK is once again the exclusive sports betting partner of Barstool Sports. The more things change, the more they stay the same.”

The Partnership, Completed at the End of the Super Bowl

The agreement could only be completed after the Super Bowl came to an end, with the Kansas City Chiefs edging the San Francisco 49ers. 

The reason was a non-compete clause that Barstool Sports had to respect. The clause referred to the closing of the company’s relationship with PENN Entertainment after the operator decided to give up on its Barstool Sportsbook in favor of a new partnership with ESPN.

PENN paid $1.5 billion to obtain the licensing rights for ESPN Bet. 

In August 2023, the most innovative provider of gaming entertainment in North America sold 100% of outstanding Barstool Sports shares to Portnoy after inking an agreement with ESPN to rebrand their current sportsbook while eliminating Barstool from the equation. 

Originally, PENN acquired a stake in Barstool in 2020, gaining complete control in February 2023 in a deal valued at $551 million that was paid over two tranches.

First on the List, a Free-Throw Challenge

The “multi-year monster deal with DraftKings,” as Portnoy called it, will first lead to the latter along with various other Barstool Sports personalities including Dave, Big Cat, Hank, Jersey Jerry, Steven Cheah, Rico Bo$co, Mark Titus, Brandon Walker, Big T, Kirk, and other Bullpen members from participating in a free-throw challenge.

The goal of the event has been set to 41 made free throws in a row, which is the National Basketball Association’s Record for most free throws in a row. 

The event will be commented on by PFT commenter Nick Turani and KB. During each new round, Portnoy and Dan will pick five participants to join them as a team and try to reach the 41 throws in a row. 

Each team member must complete at least two free throws and up to 10 free throws. Portnoy will need to hit the 15th, 30th, and 41st free throws. 

The group will start with 75 mulligans. Once all are used, the group will only receive one extra mulligan every three rounds.  

The challenge will be streamed live and incorporate a series of questions that viewers will need to answer based on what they think will happen during the stream.

Those viewers who answer the most questions correctly win a share of the set $100,000 prize pool.

Elsewhere, DraftKings executives Jason Robins, Paul Liberman, and Stanton Dodge sold close to $78.8 million worth of stock before the release of the company’s fourth quarter and 2023 results. 

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Barstool Sports, the leading sports media brand, founded by Dave Portnoy, may lay off some of its employees, its founder and current owner confirmed on Barstool Sports Radio recently. Initially founded in 2003, Barstool Sports was acquired by Penn Entertainment in a deal with a total price tag of $551 million, dating to 2020. After Penn spent years and some half a billion dollars to raise awareness of its betting brand through association with the famous sports media, the company decided to sell Barstool back to Portnoy.

Not even a full month after he retained ownership of Barstool, Portnoy confirmed the plans for layoffs. He said that he doesn’t only dislike but even hates cuts and layoffs, but pointed out that this is the only way Barstool can progress forward. According to Portnoy, the company loses more than $10 million a year, which pushed him to the difficult decision about the layoffs.

“I’ve been very clear. Anybody that’s paid attention, we are going to have layoffs and cuts, and they’ve started and it sucks. And people who know me from the beginning I hate firing people. You can be incompetent, not work and I generally don’t fire because I hate it so much. It’s the worst thing to f***ing do,“

explained Dave Portnoy on Barstool Sports Radio

Getting Back to Breaking Even

Addressing the seriousness of the situation, Portnoy said that it is a “no-brainer” considering that if there are no layoffs, everyone may lose their jobs. He stressed the difficulty of that decision and added that Barstool needs to become stable once again. Finally, Portnoy reiterated that the company is losing millions which is not a good thing.

“We’ll all not have jobs. So we have to get back to a break-even thing. We’re losing a lot and it sucks,“

added Portnoy

Barstool’s founder did not confirm how many employees will be affected by the upcoming layoffs. However, a recent report released by the New York Post suggested that the company may lay off an estimated 25% of its workforce. Currently, Barstool has approximately 430 employees. This means that approximately 100 jobs may be affected by the layoffs if that projection becomes reality.

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Gaming and entertainment giant PENN Entertainment achieved a significant milestone by successfully migrating its Barstool Sportsbook & Casino brand to its proprietary online gaming platform. This strategic undertaking marks a vital step in PENN’s digital expansion ambitions, allowing Barstool to better compete with other leading operators.

The Move Went without a Hitch

Barstool announced the planned migration on 7 July, informing customers of an impending 72-hour shutdown. Fortunately for the operator, the transition finished flawlessly across all 16 states where the brand is active, completing a significant milestone in the brand’s efforts to achieve technological independence. Barstool regarded the move as a significant achievement, allowing it to better compete with industry heavyweights like FanDuel, BetMGM, and DraftKings.

Despite the inconveniences related to the temporary shutdown, Barstool was confident the results would justify the downtime. The new platform offers a user-friendly interface, intuitive navigation, and improved features that cater to online gaming enthusiasts’ evolving needs and preferences. Head of Penn Interactive, Benjie Levy, congratulated the team on their achievement, expressing optimism for the company’s future.

I am extremely proud of our Interactive team who stepped up to the challenge to execute this complex project on time and with minimal disruption to customers.

Benjie Levy, head of Penn Interactive, president & COO of theScore

According to Levy, the migration would grant PENN’s in-house team complete control of all operations and product development, elevating Barstool’s casino experience to a world-class level. The new platform has features specifically designed for the North American market, allowing rapid expansion into new jurisdictions and swift adaptation to changing regulatory requirements.

With complete control over the technology and infrastructure, PENN Entertainment can remain flexible, introducing new features, meeting player demands, and staying at the forefront of industry trends. The new proprietary platform provides a solid foundation for Barstool’s digital expansion plans and positions the brand for continued success in the highly competitive online gaming market.

PENN’s continued investments in the Barstool brand hope to bolster its presence across the USA, improving its position in the country’s highly competitive sportsbook market. The group’s consistent Q1 results provide a stable base for expansion, while its Penn Game Studios subsidiary significantly enhanced the company’s technological base. These efforts place Barstool in the perfect position to improve its market share and grasp new expansion opportunities.

Barstool’s migration to its proprietary gaming platform signifies a significant milestone in the operator’s digital journey. The seamless transition will enhance the user experience, allow exclusive features, and expand players’ betting options. With a strong focus on security, reliability, and innovation, PENN Entertainment is well-positioned to drive growth and provide an exceptional online gaming experience for its customers, opening the doors to new and exciting opportunities.

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In mid-February, PENN Entertainment announced it finished the acquisition of Barstool Sports, Inc. after previously acquiring a 36% stake in the company three years ago. The remaining interest in the media brand specialized in sports, entertainment, and lifestyle was acquired for around $388 million.

Now, Barstool Sports has announced it leased a new office space in Chicago, this way marking its second launch in the third-largest city in the US.

While other corporations are leaving the city scared by the high crime rate, the company founded in the suburban parts of Boston decided to go forward and open a second office measuring 400,000 square feet.

The New Location to Host a Full-Size Basketball Court & a Golf Simulator

Located west of the Chicago Loop at 400 N. Noble St. nearby Fulton Market, the industrial building purchased by Jeff Shapack and Alec Litowitz will host a full-size basketball court along with a golf simulator, several music studios, and additional spaces that will be used for media creation of media content.

The new location will also be near a plethora of office and large apartment building projects that are currently under construction.

Barstool Sports’ spokesperson Debra Duffy announced that the company’s employees will swap their New York offices with the brand new Chicago office.

While these amenities are usually found with most offices belonging to gaming companies, they have gradually started to be eliminated across a number of different other industries in the context of certain corporations trying to cut their expenses to get ready for a potential upcoming recession.

Rampant Crime in Chicago Scaring Off Big Players

As mentioned earlier, the decision to open a second office also came in the context of big corporations fleeing the city because of the rampant crime rates.

The list includes prestigious names like Boeing, Tyson Foods, and Caterpillar. They all decided to relocate to different states or different parts of Illinois because of the growing crime, even though Boeing did not specifically use the city’s crime as a primary argument for the decision to relocate to Northern Virginia.

Located on the outskirts of Chicago, McDonald’s also expressed concerns regarding the criminal activity in the area, even though there are no palpable plans to move out of the city or out of state.

In 2022, American billionaire, hedge fund manager, entrepreneur, and founder, CEO, co-CIO, and 80% owner of Citadel LLC Ken Griffin announced he would be taking his $57 billion hedge fund to Miami, again using Chicago’s crime and budget woes as a main reason.

PENN Entertainment currently operates four separate casinos in Illinois while Barstool Sportsbook also provides mobile sports betting services in the Prairie State.

Barstool Sports’ first office in the Windy City is found in the Lakeview area where it hosts a sports bar in the River North.

Last November, Barstool Sportsbook went live in Maryland, allowing customers in the state to place wagers on top global sports leagues.

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Casino gaming and sports betting company PENN Entertainment announced the completion of its previously announced acquisition of the remaining share of Barstool Sports for approximately $388 million.

The acquisition of the remaining interest in Barstool Sports completed the second stage of the acquisition of the sports media brand in which PENN acquired a 36% stake in February 2020.

Pleased to welcome Barstool Sports fully into the PENN family, PENN’s chief executive officer and president, Jay Snowden, outlined Barstool’s credentials which lured PENN into the acquisition.

Barstool is a proven, powerful media brand with an authentic voice and vast, loyal audience that provides us with a strong top of funnel for new customer acquisition and organic cross-selling opportunities across our growing interactive division.

Jay Snowden, CEO & President, PENN

He further highlighted that the combination “with theScore’s reach and highly engaged user base” would help propel the brand and PENN’s integrated media and gaming business by creating “a massive digital footprint and ecosystem.”

Another benefit for Barstool would be its migration to PENN’s proprietary technology stack as it would “significantly enhance the overall product offering and deliver meaningful upside,” Snowden concluded.

Partners since 2020

PENN Entertainment initially announced the acquisition of the remaining interest in Barstool Sports in August last year after several years of working together with the brand since the $163 million initial interest acquisition deal in 2020 which followed the exclusive sports betting and iCasino partnership agreed upon by the parties in January 2020.

The acquisition took place during times when the founded as a free sports and gambling newspaper brand by Dave Portnoy in 2003 celebrates its 20^th anniversary – a period during which Barstool Sports has evolved into a major player on the digital scene, operating across sports, lifestyle and entertainment.

“Barstool Sports is bigger than ever and has become more than I ever dreamed of,” Portnoy commented, thankful to the Barstool team and everyone who has been along for the ride, looking forward to the brand’s next chapter with PENN.

Boasting a loyal fan base of over 200 million, Barstool Sports affirmed itself as a multimedia brand, creating over 100 sports and comedy shows and delivering content via span podcasts, video, social media, live events, pay-per-view, and its growing commerce business.

Also commenting on the announcement, Barstool Sports’ chief executive officer, Erika Ayers, underscored the huge moment that was made possible after a lot of effort had been put in by a lot of people, stressing Barstool’s objective of creating “relevant and entertaining content” for the fans, as well as delivering “strong results” for its partners.

“It’s exciting to have that vision recognized and to be able to put it to work inside of PENN,” Ayers added, paying tribute to “the best fan base on the planet” and eager to deliver more for the fans “with PENN’s support.”

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