Ambassador Deals Between Pro Athletes & Sportsbooks Are Booming, Erasing Stigma

Written By Brant James on July 1, 2021 - Last Updated on September 10, 2021

A few weeks before Portuguese soccer superstar Cristiano Ronaldo became a Coca-Cola brand adversary by removing a bottle of soda from the interview table at Euro 2020, one of his peers in international sports celebrity was busy making friends.

In a deal announced at the Seminole Hard Rock Hotel and Casino in Hollywood, Fla., in June 2021, Argentine megastar Lionel Messi became the first athlete brand ambassador for Hard Rock International. That encompasses the entirety of Seminole Tribe of Florida’s prized brand asset: restaurant, hotel and gambling. And therefore, it is big.

This move was not only a thunderstroke for the Seminoles, whose veritable monopoly on gambling in Florida – newly including sports betting – was hardened in May with a 30-year compact signed by Gov. Ron DeSantis and approved by the Department of the Interior in August. But it was a watershed moment for athletes lending their fame to promote legal sports betting in the United States.

Hard Rock currently takes bets only in New Jersey and Iowa, but will eventually add Florida and has global aspirations through Hard Rock Digital.

The taboo of gambling, and particularly sports betting, has been mitigated in the mainstream since 2018 and the fall of the Professional and Amateur Sports Protection Act. Professional leagues and media outlets now scramble to acquire sportsbook partners.

But whether a superstar or not, an athlete still competing as a professional and lending their personal gravitas to a gambling venture was something new.

Sure, Hard Rock is burgers and expensive jackets, too. But the Messi announcement was made at a casino property, and the former Barcelona sniper can make the company buckets of revenue by luring fans to the blackjack table.

A recent study released by YouGov and SBC Americas asserted that 35% of 18-to-34-year-old bettors deemed celebrity endorsements as a key deciding factor on which companies to patronize.

Will athlete deals with sportsbooks get … Messi-er?

Kevin Mercuri, founder and CEO of Propheta Communications, which has represented multiple gaming sector clients, once believed that athletes would never avail themselves of gambling deals until their Hall of Fame aspirations had played out. Not anymore.

“Times have certainly changed,” he told PlayUSA. “Fifteen years ago, athletes avoided sports betting for fear of running afoul of their league’s ethics guidelines. Retired athletes also avoided shilling for a sports betting site because they worried that doing so may negatively affect their Hall of Fame candidacy. We’ve worked with many sports betting sites in the past and had great difficulty finding sports figures who were willing to collaborate.

“Today, perceptions around sports betting have shifted 180 degrees. The old perception of the degenerate sports gambler has been eclipsed by newer marketing personas portraying sports gamblers as wholesome sports fans with disposable income. It’s far easier for a professional athlete to align him or herself with the industry now.”

DraftKings made a deal with US Open champion Bryson DeChambeau, and sportsbook sponsorships of NASCAR teams had begun in February with BetMGM aligning with Richard Childress Racing. But even though drivers Austin Dillon and Tyler Reddick wear the company’s signage and promote BetMGM (as DeChambeau does with DraftKings), the Messi deal feels different.

This goes beyond a logo and a name-drop and feels more like the first full-throated, compensated endorsement of gambling enterprises by an active athlete.

Can only Messi-level athletes pull this off? Only non-Americans? Mercuri wonders if these types of deals will be the start or the finish of a trend.

“It is significant in that some of these practices haven’t been adequately regulated,” he observed. “They’re not forbidden, so bold companies like DraftKings are willing to take the chance and reap the benefits. If they were to get slapped down in a year or two, they still benefitted, so why not take the chance? Americans don’t like leaving money on the proverbial table.”

So far, retired American athletes are the only ones making the grab domestically, with the exception of sponsor-driven sports like NASCAR and the PGA, which in 2020 added DraftKings as its first official betting partner.

The path in following Messi seems messy, indeed, for his American counterparts because of the murkiness of collective bargaining agreements in the “Big Four” leagues. MLB, NBA and NHL are operating under deals written before PASPA fell.

The NFL’s 2020 pact is laden with gambling stipulations, but just one ambiguous line stating that a player who “knowingly associates with gamblers or gambling activity” can be punished, when their team owners and the league itself are so at high levels.

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The PlayUSA brand athlete power poll

Let’s have some fun with this while also gauging the sheer swiftness of these deals all being put together. Compared to a few years ago, what a change of tune, indeed.

The PlayUSA poll considers career accomplishment, overall star power of the athlete and how their endorsement pushes legal sports betting further into the mainstream. Only athletes who have transacted to represent or otherwise work for a sportsbook in some official way are considered. 

  1. Michael Jordan: His gambling exploits were well-known as he was winning six titles with the Bulls and minting himself the greatest basketball player of all time. Casinos, making it interesting on the golf course, etc., even became fodder for “Saturday Night Live” sketches decades later. Now he’s a special advisor and board member at DraftKings. He’s not apologizing.

  2. Shaquille O’Neal: Already a pitchman for PointsBet in Australia, the four-time NBA champion became a spokesperson for WynnBet in the United States in August of 2021, adding gambling to his expansive business/endorsement portfolio that includes Aunt Annie’s, Papa John’s (and at one time, 155 Five Guys). He sold his stake in the Sacramento Kings by NBA rule, to enter in this deal. The Big Aristotle is being paid an equity stake in the company by PointsBet in Australia. A few years go, O’Neal filed a trademark for the brilliantly named “SHAQPOT” as a means to provide “online betting, gaming, gambling and wagering services related to sporting events.” Now ShapPot will be a free-to-play game inside the WynnBet app. This is a massive mainstreaming move for sports betting in the United States, given O’Neal’s popularity and ubiquity.

  3.  Wayne Gretzky: “The Great One” became a spokesperson for BetMGM as the operator readied to expand its American footprint and awaited the eventually successful push to legalize sports betting into Gretzky’s native Canada.

  4. Lionel Messi: 2009, 2010, 2011, 2012 & 2015 Ballon d’Or winner, La Liga all-time top goal-scorer, Argentina’s all-time top goal-scorer …. How much time do we have here? Oh, and now the public face of the Seminole Tribe of Florida.

  5. Pete Rose: The all-time hit king has made some bad choices related to sports betting, most prominently betting on baseball – including his Reds – while managing them and being subsequently banished Hall of Fame consideration. Aligning with tout service Upick Trade was another swing and a miss, but for the nexus of star power and betting proclivity, Rose is impossible to ignore.

  6. Mike Tyson: The former heavyweight champion, stage and screen actor, facial tattoo enthusiast and cannabis entrepreneur has represented Cypriot bookmaker Parimatch since 2019.

  7. Conor McGregor: The former UFC champion and Floyd Mayweather antagonist took time away from promoting his whisky brand to join Tyson at Parimatch in 2019.

  8. Brett Favre: The three-time MVP quarterback inked a multi-year deal in 2021 to become the face of BetAmerica’s transition into TwinSpires Sportsbook and its “Bet Dedicated” campaign.

  9. Cal Ripken Jr.: Baseball’s “Iron Man” became a special advisor and member of the DraftKings board in 2021.

  10. Mike Ditka: One of just two to have won a Super Bowl as a player, an assistant coach, and head coach, and the first pure tight end elected to the Hall of Fame, the Bears legend made for a savvy pick-up for Chicago-based Rush Street Interactive’s BetRivers.

  11. Barry Sanders: The Heisman Trophy winner, NFL MVP and arguably greatest running back of all time hits the holes for BetMGM’s Michigan sports betting efforts, where his former Lions team also has a sports betting deal with the company.

  12. David Ortiz: ‘Big Papi’ is a beloved three-time World Series champion, a member of the 500-homer club, a lifetime .286 hitter and a seven-time silver slugger. But when he told an aching town in a pregame ceremony the week after the Boston Marathon bombing in 2013 that “this is our f—–g city” and that they would persevere together, he became one of the most important sports icons in New England history. Throwing money at fans as part of his FoxBet duties at the All-Star game didn’t resonate as Boston-strongly, but his power to influence can’t be underestimated.

  13. Marshawn Lynch: The purveyor of “Beast Quake” joined BetMGM in July of 2021. No word on if he’s being paid in Skittles.

  14. Drew Brees: The just-retired NFL leader in several categories including regular season passing yards is a former Super Bowl winner with New Orleans and a shiny new face for sports betting for PointsBet. He could be the benevolent face of the enterprise in Louisiana and a lot of other places as a very current emissary.

  15. Charles Barkley: The Hall of Fame forward and always-interesting NBA commentator became a FanDuel content provider, brand ambassador and spokesperson in December 2020. Considering the amount of money he admits to losing while gambling, take him as a cautionary tale as you chuckle along.

  16. Pat McAfee: The former Colts kicker wields his considerable post-career social media presence for FanDuel. His sports betting, daily fantasy sports, casino, and horse racing “official provider” deal is believed to be the first between a sportsbook and a media personality.                                                    

  17. Chad ‘Ochocinco’ Johnson: An 11-year NFL career of excellence – despite controversy – provides the on-field credibility and more than five million followers on Twitter and Instagram mint him as an influencer for WynnBet, which signed him in July of 2021.

  18. Jordan Speith: The three-time major champion became the “face of FanDuel’s golf products,” according to a company release, in August, 2021. Speith won the 2015 Masters and US Open at age 21 and two years later he won the Open Championship.

  19. Allen Iverson: The 76ers legend teamed with Darrelle Revis to front PointsBet’s launch in the United States via New Jersey in 2018.

  20. Charles Woodson: The Hall of Fame defensive back and former Super Bowl champion launched a double role as a FOX Sports broadcaster and FOX Bet spokesperson in 2021.

  21. Jalen Rose: The Fab Five cornerstone was a steady NBA contributor before becoming a ubiquitous ESPN mouthpiece. He became a BetMGM man in 2021.

  22. Tim Howard: In 2014, AdWeek pondered if the goalkeeper, now a TV analyst, veteran of two World Cups and a participant in the most games ever for the US Men’s National team, was the perfect brand ambassador. That was a long time ago, but Howard’s influence and respect, especially within the soccer community, should benefit WynnBet. He joined the company in July of 2021.

  23. Terry Bradshaw: Hall of Fame quarterback shills for FoxBet with his proverbial briefcase of money during his broadcast duties.

  24. Jaromir Jagr: A hockey legend whose gambling habits caused the NHL consternation, Jagr has lent his image and name to a line of casino games.

  25. Shannon Sharpe: The Hall of Fame tight end for the Broncos is another of the heavily leveraged Fox celebrities.

  26. Howie Long: The NFL Hall of Famer is a frequent and apparently eager mouthpiece for FoxBet as part of his weekly NFL commentary duties.

  27. Kenny Smith: The two-time NBA champion and analyst for TNT’s “Inside the NBA” landed his own content deal, as FanDuel is now his exclusive sports betting and daily fantasy provider.

  28.  Mark Schlereth: “Stink,” a three-time Super Bowl champion, 12-year guard and veteran broadcaster, joined BetRivers in August of 2021 to create “unique content for Broncos fans throughout Colorado and NFL fans throughout the U.S., on the BetRivers and PlaySugarHouse platforms,” according to a press release.

  29. Bryson DeChambeau: The US Open champ became the first active player to represent DraftKings golf products in a deal announced in November of 2020. The blame-the-driver incident and vaccine obstinance after missing the Olympics with a positive COVID test hurt him.

  30. James Harrison: The former Steelers linebacker, investigated by the NFL in 2017 for co-hosting a charity arm-wrestling match in a casino, amused everyone in a FanDuel commercial.
  31. Darrelle Revis: A four-time All-Pro and Super Bowl winner, Revis became a spokesperson for PointsBet in 2019, lending his reputation as a Jet to promote the company in New Jersey.

  32. James Blake: A winner of 10 singles and seven doubles titles over a 14-year-career, the American climbed as high as No. 4 in the world rankings in 2006. In August of 2021 he signed up to serve as a brand ambassador for BetRivers.

  33. Kevin Harvick: A former NASCAR Cup series champion and Daytona 500 winner, the veteran became a Unibet ambassador in June of 2021 when his Stewart-Haas Racing team acquired an official sportsbook partner.

  34. Morton Andersen: The “Great Dane” and NFL Hall of Fame kicker is a ubiquitous figure at national sports betting conventions, schmoozing conventioneers with his gold jacket and free-flowing Carlsberg beer.

  35. George Karl: Sixth on the all-time wins list for NBA coaches – he was a player, too! – Karl has a BetRivers content deal under the “Bet With A Winner” campaign.

  36. Rip Hamilton: The NBA champion and three-time all-star became the face of PointsBet‘s expanded sportsbook deal with his former Pistons teams in 2021.

  37. Devin Hester: One of the greatest punt-returners in NFL history made a fair catch for PointsBet as a business partner before it readied to enter the Illinois sports betting market in 2020.

  38. Martin Gramatica: “Automatica” debuted in a short DraftKings spot during the 2021 NFL-season-opening Bucs-Cowboys affair, undoubtedly confusing locals who either didn’t know legal sports betting would soon be available or that DraftKings is likely to be shut out by Hard Rock Digital.

  39. Clint Bowyer: The gregarious former NASCAR driver is a member of the integrated Fox Sports and FoxBet enterprise.

  40. Paige Spiranac: The former pro golfer and social media juggernaut now drives links for PointsBet.
  41. Austin Dillon: The former Daytona 500 winner advocated sports betting as an engagement tool before it was cool or lucrative or even encouraged by NASCAR. The multi-race sponsorship deal his Richard Childress Racing team struck with BetMGM this season is the first in North American motorsports.

  42. Bubba Wallace: His 23XI race team – which is co-owned by Jordan – will sport DraftKings signage this season, though so far it’s been as a sticker instead of a full paint scheme. As part of the agreement, DraftKings became the official sports betting partner for the team of Wallace, a six-time truck series winner and the only full-time African American driver in Cup.

  43. Notah Begay III: The four-time winner on the PGA TOUR is an NBC Sports and GOLF Channel analyst, hired in August, 20211 to serve multiple advisory and functional roles with PointsBet, including ‘golf ambassador.’ He’s the only full-blooded Native American to play on the PGA TOUR and one of three in the history of professional golf to shoot a 59 in a PGA Tour sanctioned event.

  44. Tyler Reddick: The younger (25) and so far winless member of the RCR Cup roster also brandishes the BetMGM scheme in various races but won’t be a potent pitchman until he becomes a recognizable figure outside NASCAR.

  45. Eddie George: Legendary Titans running back became the benevolent face of FanDuel for the launch of Tennessee sports betting. That relationship would figure to end now that he’s the head coach at Tennessee State, but he had a good … run. He should be much higher on the list, but he’s inactive while coaching.

  46. Nick Mangold: The seven-time Pro Bowl offensive lineman for the Jets became a WynnBet spokesperson in July of 2021. To this point, Mangold seems bad at bets.

  47. Anthony Alfredo: GoldenNuggetCasino.com signed on as a primary sponsor for the Front Row Motorsports driver in two races in the 2021 NASCAR Cup season.

Honorable mention:

Gisele Bündchen – The philanthropist, environmentalist and former supermodel is a special advisor to DraftKings’ Board of Directors. While those jobs (and former one) are undoubtedly notable on their own, the Brazilian makes this specific list because she might one day be able to one day grease the skids for husband Tom Brady to join the board, and, therefore this list. Although, his NFT deal might get him there on his own.


American sportsbook ambassador list

PointsBet (7): Shaquille O’Neal, Drew Brees, Allen Iverson, Darrelle Revis, Devin Hester, Paige Spiranac, Notah Begay

BetMGM (6): Wayne Gretzky, Barry Sanders, Marshawn Lynch, Jalen Rose, Austin Dillon, Tyler Reddick

FanDuel (6): Charles Barkley; Pat McAfee, Jordan Speith, Kenny Smith, James Harrison, Eddie George

FoxBet (6): David Ortiz, Charles Woodson, Terry Bradshaw, Shannon Sharp, Howie Long, Clint Bowyer

BetRivers (5): Mike Ditka, Mark Schlereth, James Blake, George Karl, Rip Hamilton

DraftKings (5): Michael Jordan, Cal Ripken Jr., Bryson DeChambeau, Martin Gramatica, Bubba Wallace

WynnBet (4): Shaquille O’Neal, Chad Johnson, Tim Howard, Nick Mangold

Hard Rock (1): Lionel Messi

TwinSpires (1): Brett Favre

Unibet (1): Kevin Harvick

Photo by Kin Cheung / Associated Press
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Brant James

Brant James is a veteran journalist who has twice been recognized in the Associated Press Sports Editors Awards, most recently in 2020. He's covered motorsports, the National Hockey League and Major League Baseball among a myriad of others beats and written enterprise and sports business for publications including USA TODAY, ESPN.com, SI.com.

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