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Massachusetts Sports Betting: Penn Took Wagers On NFL Game After It Ended

Bill Speros for Bookies.com

Bill Speros  | 22 mins

Massachusetts Sports Betting: Penn Took Wagers On NFL Game After It Ended

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BOSTON –  Penn Sports Interactive had nearly $50,000 in Massachusetts sports betting player prop wagers voided from the New York Giants-Arizona Cardinals game in Week 2 because the bets were placed after their outcomes were determined. 

Penn Sports Interactive (PSI) told the Massachusetts Gaming Commission 257 player prop wagers in 10 different markets were placed in Massachusetts on its Barstool Sports app after the conclusion of the Giants vs. Cardinals Week 2 NFL game played on September 17 in Glendale, Arizona. 

The operator said 59 customers placed $47,759.94 in wagers up to 90 minutes after the Giants 31-28 comeback victory. Similar wagers were reported in at least two other states, but likely occurred elsewhere. None of the wagers were paid. 

PSI is licensed in 16 states. Last month, it entered into a 10-year marketing and branding deal with ESPN Bet that carries a $150 million annual price tag. It also grants ESPN $500 million of stock warrants to buy approximately 31.8 million common shares of Penn. Simultaneously, PSI sold Barstool Sports back to Dave Portnoy for $1. 

The books are still being operated under the Barstool brand as the transition is not expected to be completed until later in the fall. ESPN Bet needs vendor approval in each state where PSI is licensed. 

How The Bets Were Allowed?

According the an item in the September 19 meeting agenda, PSI said the "primary root cause of the issue" occurred due to "technical data breakdown" with odds provider Swish Analytics.

"The secondary cause" occurred after their sports trading platform Vegas "experienced a significant increase in activity" at 4:15 p.m. Eastern, following the start of the day's late NFL games. The surge slowed the platform's ability to update its displays. Only once the latency issue was resolved, PSI confirmed the wagering anomalies on the event.

PSI said Swish Analytics is expected to have its issues resolved to process all player prop market updates and values with a "manual" fix ahead of the Week 3 NFL game Thursday night between the New York Giants and San Francisco 49ers.

MGC staff said the the company's provider could only process whole numbers. So wagers concerning items such as "1.5 sacks" or "1.5 interceptions" slowed the system. Wagers were placed as soon 6:02 p.m. after some of these props have already been decided. 

Also Thursday, Boston-based DraftKings received a brief extension to implement a regulation that mandates operators place "Over 21" language on fixed free-standing signage using the company's branding. BetMGM has already added "21+ To Wager" language to its painted sign on the Green Monster in Fenway Park. DraftKings has signage at Fenway Park, TD Garden, and inside Gillette Stadium, which it wanted fully exempt from the rule. The MGC is expected to revisit this issue in October. 

The MGC also agreed to add World Jai Alai wagering to the state's betting catalog.

Betting Numbers Rebound In August

Legal sports betting on the state's eight licensed mobile sites and three retail sports books saw a total handle of $314,923,841.60. That represents a 6.78% from the same figure in July. A total of $2.567 billion in bets have been settled since retail sports betting launched on January 31,

Operators and regulators are expecting a major spike in September with legal NFL betting taking place in Massachusetts for the first time. According to data from GeoComply, 9.2 million geolocation checks took place in the Bay State during Week 1 of the NFL season from Sept, 3-10. The company said there are 383,000 active online/mobile accounts in the state, while 59,000 new accounts were created during that same period. 

July's betting handle released was $294,924,777.29 for combined retail and mobile operations. That was the lowest in terms of handle, mobile sports betting began on March 10, continuing a trend that began in May. 

DraftKings Continues To Dominate Massachusetts Market 

DraftKings led the state in online handle for the sixth consecutive month in July with $161,921,969.35. Its hold stumbled to 6.9%, down from 10.17%. FanDuel held second place with $$79,421,282.92 in total handle and a hold of 9.60%, or more than $7.62 million. Both companies displayed adjusted net positive revenues overall in the the second quarter nationwide in earnings reports released this month. 

On the retail side, the WynnBET Encore Boston led with in 3,959,509.00 in handle, but it booked a loss of $48,027.

The state collected $4,542,587.68 in tax revenue from both its eight mobile and three retail sports betting sites in June. In total, sports betting has generated $50.35 million in tax revenue after just 165 days of mobile betting and four months plus one day of retail betting. Projections had the state making between $60-70 million in sports betting tax revenue per year.

According to a Bookies.com analysis of reported betting handles across the United States in the month of April, Massachusetts had the second-highest per-capita handle of any other legal start in the nation outside Nevada. New Jersey was first. 

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Raynham Park Seeks Partner, License On Hold

After Caesars Sportsbook pulled out of its deal to run a sports book at Raynham Park, the facility's owners Massasoit Greyhound Association will not be getting a sports betting license until they land a new partnership. 

Caesars terminated its operating lease agreement with the owners of Raynham Park and withdrew its application the MGC run the sportsbook at the former greyhound racing facility south of Boston in August. It would be the fourth retail betting site in the state.

The gaming commission voted to remove Christopher Carney from MGA's application. He is the son of longtime Raynham Park owner George Carney. That was a pivotal move given the concerns Christopher Carney's presence on the license raised with regulators. 

Raynham Park's retail sports betting license has featured five separate days of hearings going back to June. MGA asked to remove the younger Carney from its application on August 1.

Details of the MGC investigation into the Carney family found several violations cited by the Massachusetts Department of Environmental Protection concerning the handling and disposal of hazardous and/or construction-related materials were committed by companies operated by the Carney family. Those violations and the subsequent fines were not initially disclosed during the MGC's investigative process. 

MGC Interim Executive Director Todd Grossman said the MGC could not make a final decision on the license application given Caesar's removal from the process. 

"MGA is today without an entity to operate its sportsbook," Grossman said. "It would not be prudent to continue the review of MGA's application as planned where Caesars' role is a substantial part of the submitted application. As a matter of law, it's difficult to envision the applicant's move toward a temporary license being granted by the Commission." 

Neither Caesars nor representatives of the Carney family have responded to requests for comment. 

Caesars To Take Over WynnBET Encore Boston Harbor Book?

Caesars' mobile sports betting license in the state is tethered to the WynnBET-owned and operated Encore Boston Harbor casino. WynnBET last week closed its mobile sports book operations in eight states. Its online book is currently running in just Massachusetts and Nevada. 

WynnBET has said publicly that it has no plans to make any changes in its Massachusetts app and its retail book at Encore Boston Harbor. Industry sources, however, believe Wynn could make a deal with another operator to run its retail book in Everett. Given that it has already partnered with Caesars for a mobile license, a deal between Caesars and WynnBET on the retail side to run the sports book at Encore Boston Harbor would be feasible for both sides.

The first hearing on a potential Raynham Park betting license on June 12 lasted for more than 6 1/2 hours. The hearing was continued briefly on June 20. The request to withdraw Christopher Carney was not made until July 27.

The MGC and attorneys representing Massasoit Greyhound Association and Carney discussed how to proceed with the matter for 2 hours on August 1 before the Commission voted to move the matter back until Friday. Previously, attorneys told the Commission that Christopher Carney is not now and never has been an employee or officer of Raynham Park. 

That contradicts multiple local news stories in recent years that have named the younger Carney as an owner and/or operator of the facility. 

The former greyhound track and current simulcasting facility located south of Boston first opened in 1940. It was purchased by George Carney in 1966.

Among 'Largest Sports Gaming Destinations' In US 

The Raynham Park Sportsbook is projected to cover approximately 30,000 square feet. The book had originally been projected to open in June. The book requires both a license and a Certificate of Occupancy are issued by the MGC.

Massasoit Greyhound Association is still free to partner with up to 2 mobile operators, but has yet to do so. The other potential Category 2 licensee in Massachusetts, Sterling Suffolk Racecourse (Suffolk Downs), has yet to submit a formal application to the MGC. 

Raynham Park ran greyhound races from its pre-WWII opening until that sport was outlawed in the Bay State in 2009. 

“Our sportsbook will be one of the largest sports gaming destinations, not only in Massachusetts, but in the United States," Raynham Park owner Chris Carney has said.

Raynham had initially chosen bet365 as its mobile partner, but bet365 no longer plans to operate in the Commonwealth after voicing concerns over excessive regulation. A Massasoit Greyhound Association spokesman told Bookies.com its mobile license "remains open".

Suffolk Downs may be considering a downtown Boston site for its retail sportsbook. Its owners have not announced any plans, or even if they plan to partner with any outside operators. The former thoroughbred racing operator has been linked to BetRivers but could also partner with DraftKings to give the company a retail site in its home state. Suffolk has yet to submit its application.

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DFS Battle Lines Drawn In Bay State

Massachusetts Sports Betting: Penn Took Wagers On NFL Game After It Ended 1

The MGC has begun to examine what it terms to be the "overlap" between some daily fantasy sports activities and sports betting. The Commission collects taxes from both and DFS operators in the Commonwealth. 

On August 8, Grossman said the MGC noted that there's been "of late, a great deal of activity surrounding the boundaries of sports wagering relative to daily fantasy sports and whether there's been some overlap between the two." 

Some DFS activities being offered have been considered sports betting activities elsewhere, Grossman said. He said an investigation is underway into the situation in Massachusetts and that the MGC could address this at a future date. 

A schism in the DFS space has developed. Established operators such as DraftKings and FanDuel who also operate in the regulated sports betting space believe some DFS operators are essentially offering prop bets and parlays under the guise of fantasy. Those on the other side, including PrizePicks and Underdog Fantasy, argue these plays fit within the fantasy sports space. 

Grossman's remarks are seen at the very least a nod to the licensed sports betting operators that the MGC is looking into the matter. 

Several DFS companies have been in the news as of late. Last week, Betr launched Betr Picks, a pick ’em-style fantasy game in 24 states. Among those were Florida, California, and Texas. None of those three states, the three largest (by population) in the nation, have sports betting up and running. Betr has a Category 3 mobile betting license in the Bay State. It is noteworthy that Betr did not launch Betr Picks in Ohio and Massachusetts, the two states in which it currently is a sports betting licensee. 

DFS operator No House Advantage has been accused by customers on social media of not paying on attempted withdrawals. Attempts to reach that company or its founder, Kevin F. Koeppel, have been unsuccessful. 

3 Massachusetts Sportsbooks Fined Total Of $50K

The three retail sportsbook operators in Massachusetts have been fined a combined total of $50,000 for taking illegal wagers on games involving in-state colleges this past February. 

The announced fines for MGM-Springfield, Plainridge Park Casino, and Encore Boston Harbor on July 24 after each book accepted bets on basketball games involving teams based in the Bay State. The law in Massachusetts prohibits wagering on in-state colleges unless they are involved in a tournament involving four or more teams. All of the operators fined self-reported the incidents and cooperated with the MGC in its investigation.

EBH accepted one wager on February 2, 2023, Boston College vs. Notre Dame women’s regular season basketball game at a kiosk through its WynnBET-branded book. The wager was part of a parlay. The fine was $10,000. The book subsequently stopped taking wagers on all women's college games to avoid any such errors in the future. 

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MGM-Springfield was fined $20,000 after it took wagers on two Harvard University men's basketball games on Feb. 3 and 4 (against Yale and Brown, respectively) at its BetMGM-branded book. Wagering was offered for approximately 21 hours and 20 hours on each event respectively, and twenty-eight tickets were sold that included wagers on the two events. 

All wagers were placed at kiosks, and two winning tickets were redeemed at the book's counter. Two other winning tickets were redeemed at a kiosk. BetMGM had incorrectly designated Harvard as being in Connecticut. The Cambridge-based university opened its doors in 1636. 

PPC was fined $20,000 after taking 33 wagers across 27 tickets on February 2, 2023, Merrimack College vs. Long Island University men’s regular season basketball game. Its Barstool-branded book incorrectly listed Andover-based Merrimack as being located in Florida. 

DraftKings Awaits Possible Fines From MGC

Boston-based DraftKings told the Commission that from March 10-22, it accepted a total of 864 wagers on three separate Universal Tennis Pro Series (UTR) events. The bets totaled $7,867. Betting on the UTR circuit is not allowed in the Bay State. 

An adjudicatory hearing on those tennis bets was held on July 24.  

The bets began on the day mobile betting launched in Massachusetts and continued until a member of the DraftKings compliance team realized the error 12 days later, the MGC said. In reporting the violation during a regularly scheduled meeting of the Commission, Zachery Mercer of the MGC said DraftKings blamed a "miscommunication between the trading team and the trading compliance team." 

The DraftKings tennis betting team copied the list of events that included UTR from another jurisdiction, MGC said, and subsequently removed the UTR circuit from its site, Mercer said. 

It is not known when the MGC will issue its finding and/or penalties in this case.

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Barstool Sports 'Can't Lose Parlay' Investigation Continues

Even though PENN Entertainment has sold Barstool Sports back to Dave Portnoy, the MGC's investigation into potential a potential gaming violation that occurred on the Barstool site in March continues.

Former MGC Internal Enforcement Bureau Director Loretta Lillios (who has since retired) in August said the review of Barstool Sports  is "still a relevant matter." Her remarks followed the news that PENN sold Barstool to back to Portnoy for $1 and joined forces with ESPN BET

PENN hopes to fully rebrand to ESPN Bet in the Massachusetts sports betting market by November, but no later than February of 2024. Commissioners said they will invite executives from PENN to speak. 

The company holds the retail sports betting license at Plainridge Park Casino in Plainville and the mobile license is currently being operated under the Barstool brand. 

PENN  announced a $2 billion, 10-year sponsorship deal with ESPN on August 8. 

PENN awaits word on any fines or penalties after an adjudicatory hearing of the MGC on June 7 over alleged violations of sports betting marketing regulations. When mobile sports betting launched in Massachusetts on March 10, a "Big Cat Can't Lose Parlay" was promoted on the Barstool Sports "interface" and in a tweet from Portnoy.

Penn Sports Interactive, a subsidiary of PENN Entertainment, was the first operator to face such a hearing for alleged violations concerning laws governing marketing and promotion that prohibit content that is "deceptive, false, misleading, or untrue, or tends to deceive or create a misleading impression." 

A two-hour hearing included the so-called "Crunch Berry Defense" used by Penn's attorneys to defend the promotion. The MGC will issue its finding, which could include fines and penalties, in writing. There is no set timetable to do so. 

The matter was initially raised during an MGC meeting on March 15. During that meeting, Lillios told the Commission about the wager, named for Barstool personality Dan "Big Cat" Katz. At that time, the MGC agreed to commence the investigation, set a hearing, and formally alert Penn Sports Interactive of the matter. 

The parlay in question focused on four college games: Ohio State vs. Michigan State, UAB vs. North Texas, Ohio vs. Toledo, and Indiana vs, Maryland. The promoted parlay hit. That same day, Portnoy shared a photo of the bet slip from the Barstool app showing he bet $13,458.70 on the parlay. 

PSI representatives notified the Commission about the CLP promotion two days after it occurred. Barstool has yet to offer the "Can't Miss Parlay" in Massachusetts since. Its attorneys said during the June 7 hearing. It is willing to permanently terminate the offer and do so in writing.

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Who Are The Players In Massachusetts?

State law allows for a total of 7 mobile betting licenses not tied to current casinos or parimutuel sites. Of those 7 slots, only four have been taken. 

The law also allows each of the state's three casinos and two licensed parimutuel sites to operate both a retail book and partner with up to 2 different mobile operators. The retail books can be run by any vendor chosen by the casino or racing operator. 

Category 1: Casino Retail (Operator)

  • Encore Boston Harbor (WynnBET)
  • MGM Springfield (BetMGM)
  • Plainridge Park Casino (Barstool)

Category 2: Racing Retail

  • Raynham Park - Awaiting Approval
  • Suffolk Downs - Pending (TBA)

Category 3: Mobile

  • DraftKings
  • FanDuel
  • BetMGM (Partner with MGM Springfield)
  • Barstool Sportsbook/ESPN Bet (Partner with PPC)
  • Caesars (Partner with EBH)
  • WynnBET (Partner with EBH)
  • Fanatics
  • Betr
  • Bally Bet (2023 Launch)
  • Betway (Q1 2024 Launch)

Since mobile betting began, DraftKings has dominated the market in handle, with FanDuel a distant second. 

Fanatics Becomes 8th Massachusetts Sportsbook

Fanatics Sportsbook began operations in Massachusetts in June. It became the 8th online book in the state. The operator said it "moved up our timelines" and invited a select group of its current customers in Massachusetts to download the app and join its "extended beta testing program" while others can download the app to join a waiting list.

The operator is officially licensed as FBG Enterprises Opco, LLC. Fanatics. 

The micro-betting site Betr began full cash-wagering operations in Massachusetts on May 10, becoming the seventh online wagering operator in the Commonwealth. Betr joined Caesars Sportsbook, BetMGM Sportsbook, WynnBET, FanDuel, Barstool/ESPN  Bet and DraftKings. 

Fanatics has a deal to buy PointsBetUSA for a reported $150 million. This industry-wide consolation will intensify in the coming year and will impact the market when it comes to consumer choice. PointsBetUSA had been given conditional approval to operate in Massachusetts but pulled out of the state before paying the $1 million annual fee. 

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Bally Bet has also been approved but won't go live until later in 2023. Betway won't launch until the first quarter of 2024. 

Betr offers a different product than the other books operating in Massachusetts. The site, co-founded by influencer Jake Paul and Joey Levy, views itself as a "disruptor" in the legacy sports betting space. Betr is also operating in Ohio. Its app is available on both the Android and iOS platforms. 

Betr focuses on both traditional pre-game and live betting, but also offers action on individual plays, such as at-bats, team possessions in basketball, and play and drive outcomes in NFL and college football games.

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How Sports Betting In Massachusetts Works

The law allows Massachusetts betting apps to serve those over 21 and physically present in the state.

Here’s an outline of the new law’s highlights:

Category Final Law
Retail Operator Tax15%
Mobile Operator Tax20%
Est. State Annual Revenue$60M
Minimum Age21
Betting Appsup to 15
College BettingOut of State teams*
Credit CardsProhibited from funding accounts
Debit CardsPermitted to fund accounts
Advertising LimitsNone
Licensing Fee$5M for 5 Years

* - College wagering for in-state schools is allowed for teams participating in tournaments that feature four or more teams, which would include the NCAA Hockey and Basketball Tournaments, ACC and Ivy League championships, and ice hockey’s Beanpot

History Of Massachusetts Betting

The Massachusetts Lottery celebrated its 50th anniversary in 2022. Gambling legislation in Massachusetts goes back to 1719, when the first laws were passed to prohibit lotteries. The first state lottery in Massachusetts was legalized in 1745 before it was outlawed again in 1833.

Parimutuel betting on horse and dog racing was legalized in 1934. Suffolk Downs was a mainstay on the national thoroughbred racing circuit until its final race in 2014. Greyhound tracks in Massachusetts included sites in Taunton/Raynham, Revere, and Plainfield. A 2009 law outlawed dog racing in the state.

Plainridge Park Casino in Plainfield hosts a limited harness racing season. Foxboro Raceway operated harness racing from 1947 to 1997 on what is now the current site of One Patriot Place, adjacent to Gillette Stadium.

Illegal betting has been a part of the fabric of the Bay State for centuries. Illegal bookmakers remain common place. A point-shaving scandal rocked Boston College in 1978-79 and was a real-life connection to the move “Goodfellas."

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About the Author

Bill Speros for Bookies.com
Bill Speros
Bill Speros is an award-winning journalist and editor whose career includes stops at USA Today Sports Network / Golfweek, Cox Media, ESPN, Orlando Sentinel and Denver Post.