Power Poll: Ranking The Top Deals Between Sportsbooks & Pro Athletes

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.

Shaquille O’Neal: 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 into this deal. A few years ago, 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.
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.
Charlie Blackmon: The 35-year-old Colorado Rockies outfielder and 2017 National League batting champion signed an $1 with MaximBet in April, 2022. Blackmon became the first active Major League Baseball player to endorse a sportsbook after players earned that right in the 2022 Collective Bargaining Agreement that ended a 99-day lockout. MaximBet’s modest national reach, currently, tempers the deal, but it could unleash a raft of followers among the larger national sportsbooks with suddenly empowered superstars.
Jerry Rice: DraftKings deployed the greatest wide receiver of all time for a series of humorous television ads surrounding the Super Bowl in 2022.
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.
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?
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.
Mike Tyson: The former heavyweight champion, stage and screen actor, facial tattoo enthusiast and cannabis entrepreneur has represented Cypriot bookmaker Parimatch since 2019.
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.
The Manning Family: This one is a bit unfair, but this cast of Mannings – Archie, Peyton, Eli and …. Cooper? – joined the Caesars brand ambassador program as a powerhouse bloc in November of 2021. The pact is particularly interesting in how it can help Caesars dominate in Louisiana, where it has already snagged the naming rights to the Superdome. The Mannings, after all, maintain deep roots in New Orleans. Per a Caesars release: “For 35 of the NFL’s 102 seasons, there was a Manning family member starting at quarterback in the league. During their illustrious NFL careers, Archie, Peyton, and Eli combined for 48 seasons, 653 games, four Super Bowl championships, 20 Pro Bowls, 152,874 passing yards and 1,030 passing touchdowns. Even after retiring 37 years ago, Archie is the second-leading passer in New Orleans Saints history. Peyton, who starred in Indianapolis and Denver, was named NFL Most Valuable Player five times, two more than any other player in league history. Eli owns almost every passing record from his time in New York and is one of five players to be named Super Bowl MVP multiple times.” Caesars went long in signing their first sports betting brand ambassadors. In June of 2022, Caesars announced a deal with Peyton Manning’s Omaha Productions to launch a “full-service audio productions network.”
Cal Ripken Jr.: Baseball’s “Iron Man” became a special advisor and member of the DraftKings board in 2021.
Connor McDavid: A Hart Trophy and a cringe. The Edmonton Oilers superstar and reigning NHL most valuable player was announced as a BetMGM brand ambassador on March 4, 2022. He became the first active pro athlete in a North American top-four league (NFL, NBA, MLB, NHL) to enter into such an association. This is a big, big, ice-breaking deal, and honestly, an iffy look for the NHL. The league was obviously on board, though. Said NHL deputy commissioner Bill Daly to Catena Media, the parent company of PlayUSA: “We have negotiated extensively with the NHLPA over how, and on what terms, we can and will permit these types of relationships. We are very comfortable that we ultimately were able to strike the right balance, and that we incorporated appropriate and sufficient safeguards to ensure the integrity of our competition.” Game on.
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.
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.
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.
Marshawn Lynch: The purveyor of “Beast Quake” joined BetMGM in July of 2021. No word on if he’s being paid in Skittles.
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. Also, go check out his comments about the proliferation of sports betting in the United States.
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.
Drew Brees: The 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.
Auston Matthews: The Toronto Maple Leafs star signed a deal to promote the gray market Bet99 brand in Canada in February of 2022. He wasn’t technically the first active team sports athlete to ink a sports betting brand ambassador deal because he was technically promoting a free-to-play game. But the skate was right on the line.
Terry Bradshaw: Hall of Fame quarterback shills for FoxBet with his proverbial briefcase of money during his broadcast duties.
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. It must not have gone well. The company announced in 2022 that it would discontinue sports betting and iGaming.
Kevin Garnett: A former NBA champion and MVP in 2004, Garnett joined BetMGM in 2021. His gambling universe credibility includes playing a fictionalized version of himself in the 2019 movie Uncut Gems.
Julian Edelman: The three-time Super Bowl champion wide receiver used to catch passes from Tom Brady, but goes deep for WynnBET these days.
Henrik Lundqvist: A Ranger goaltender for 15 seasons and a future Hall of Fame lock, the Swede latched on with Caesars the weekend mobile sports betting launched in New York.
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.
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.
Allen Iverson: The 76ers legend teamed with Darrelle Revis to front PointsBet’s launch in the United States via New Jersey in 2018.
Rachel DeMita: The former All-American basketball player at Old Dominion University, first person to host a TV show through a video game (NBA 2KTV) and Instagram celebrity signed a deal as a content producer and brand ambassador with Caesars in December of 2021. She’s the highest-ranking female on the PlayUSA power chart.
Joakim Noah: A two-time NCAA champion at Florida and a nine-year vet of the Bulls, Noah signed on with Chicago-based Rush Street Interactive in March of 2022.
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.
Jalen Rose: The Fab Five cornerstone was a steady NBA contributor before becoming a ubiquitous ESPN mouthpiece. He became a BetMGM man in 2021.
Chris Long: A former No. 2 overall draft pick and two-time Super Bowl champion, Long blitzes for WynnBET these days.
Bobby Valentine: The former Major League Baseball player and outspoken Mets and Rangers manager joined BetRivers in January of 2022 to pitch the brand’s products and offer his copious opinions in a content campaign.
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.
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.
Shannon Sharpe: The Hall of Fame tight end for the Broncos is another of the heavily leveraged Fox celebrities.
Howie Long: The NFL Hall of Famer is a frequent and apparently eager mouthpiece for FoxBet as part of his weekly NFL commentary duties.
Chris Johnson: The Titans legend led the NFL with 2,006 rushing yards in 2009 and is just outside the league’s top 25 all-time. He took the handoff from BetMGM in November, 2021.
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.
AJ Andrews: A standout at LSU, a Major League Baseball Network analyst, and the first female to win the Rawlings Gold Glove Award while playing professional softball, Andrews joined BetMGM as a spokesperson and content creator in March of 2022.
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.
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.
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.

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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.
Amanda Serrano: A seven-division boxing champion and the first woman to headline a card at Madison Square Garden, she joined the FanDuel fold in April of 2022.
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.
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.
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.
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.
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.
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.
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.
Clint Bowyer: The gregarious former NASCAR driver is a member of the integrated Fox Sports and FoxBet enterprise.
Paige Spiranac: The former pro golfer and social media juggernaut now drives links for PointsBet.
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 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.