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Trump Says Pete Rose Had “Bad Timing,” As LeBron James Rides To Work Every Day In A Helicopter From Fanatics, Which Also Runs A Sportsbook

The president called Pete Rose unlucky while LeBron James rides a helicopter owned by a company running a sportsbook. Two October moments reveal just how tangled money, gambling, and sports have become.

By AJ Tiarsmith
Published October 9, 2026, 5:46am ET · 3 min read

Market Pulse desk. Editor: AJ Tiarsmith, PhD.

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President Trump at White House
Donald Trump points to reporters as he takes questions in The Oval Office © Shutterstock

Two scenes from October show how far sports gambling has moved. The president called baseball’s most famous banned gambler unlucky. Meanwhile, LeBron James commutes by helicopter owned by a company that also runs a sportsbook.

A Rally Aside on Pete Rose

Yahoo and MySA reported that the president said he would award former pitcher Roger Clemens the Presidential Medal of Freedom. According to a transcript of his rally in San Antonio, the president then turned to Pete Rose, according to The Singju Post. He said Rose had “bad timing” and that life is all about timing. He also said Rose always bet on “his own team.”

Two Claims That Need Dates

Rose died in September 2024. Major League Baseball reinstated him on May 13, 2025, making him eligible for the Hall of Fame ballot, though he has never appeared on one.

Sports betting is legal in 39 states plus the District of Columbia as of May 2026. Baseball imposes a lifetime ban for betting on games in which a person has a duty to perform. The other major leagues also bar betting on their own sport.

A Helicopter Commute Under a Card Deal

Front Office Sports reported that James’ Fanatics deal includes helicopter use. Bleacher Report linked the flights to his Fanatics contract, and PhillyVoice reported the rides are paid for by Fanatics. James signed the trading card partnership in January 2024. It reportedly runs past his playing career, and its value has not been disclosed. A James spokesperson confirmed that the deal, signed “almost three years ago,” includes access to Fanatics’ corporate aviation.

Flight records show that a Leonardo AW139 with Fanatics graphics made about 12 round trips between Philadelphia and New York in the week before the Front Office Sports report. Those records follow the aircraft and do not list passengers. They show how often the helicopter flew. Gulf News described James as paying $0 for the trips.

Fanatics also runs sportsbooks and a prediction market. In September 2026 it launched one app that combines its sportsbook, iGaming and prediction market products. The helicopter is a corporate aircraft provided under the merchandise deal.

A $15 Million Endorsement on the Side, according to Yahoo Sports

Yahoo Sports reported that James’ separate deal with Polymarket is worth $15 million a year. The same outlet later reported that he will make nearly 4x more from Polymarket than from playing for the 76ers, according to Yahoo Sports. His contract is a two-year, $8 million deal that pays $3.87 million this season. Reports describe his Polymarket role as solely promotional, in a campaign centered on football.

Yahoo Sports has run several critical pieces. One covered the $15M deal amid questions over betting legality, according to Yahoo Sports. Another said his Polymarket deal raises questions for the NBA, according to Yahoo Sports. A third described growing scrutiny of the $15 million deal after his comments about Victor Wembanyama, according to Yahoo Sports. League rules do not bar players from backing prediction markets.

Leagues Have Signed On

The Supreme Court cleared the way for legal sports betting in 2018. US sports betting revenue reached $16.96 billion in 2025, growth of 22.8% on $166.94 billion wagered.

MLB announced an official Polymarket partnership on March 19, 2026. The NHL signed with Polymarket and Kalshi in October 2025. The NBA is reportedly in talks but has not signed a deal.

Lifetime Bans Still Land

Betting has led to live scandals. The NBA banned Jontay Porter for life in April 2024. On October 23, 2025, federal authorities arrested three people connected to basketball on betting-related charges. Those cases remain open.

A Sponsor With a Rulebook Attached

Rose bet in secret and lost everything. Today betting sponsors the sport, on jerseys, in apps and through league partnerships. Betting by people inside the game is still prohibited, and lifetime bans are still being handed down. That gap between the sport’s commercial position and its disciplinary rules shapes how leagues now police gambling.

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AJ Tiarsmith

AJ spent 10 years writing about financial markets at The Motley Fool. His coverage centers on technology stocks and the broader macroeconomic trends, from interest rates to geopolitics,  that shape where markets are headed next. AJ is drawn to the stories where big-picture economics and individual companies collide.

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