Charles Barkley made an insane Western Conference bet on national television

NEW YORK, NY - JUNE 26: Charles Barkley speaks onstage during the 2017 NBA Awards Live on TNT on June 26, 2017 in New York, New York. 27111_002 (Photo by Kevin Mazur/Getty Images for TNT)
NEW YORK, NY - JUNE 26: Charles Barkley speaks onstage during the 2017 NBA Awards Live on TNT on June 26, 2017 in New York, New York. 27111_002 (Photo by Kevin Mazur/Getty Images for TNT) /
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The TNT analyst placed a hefty long-shot wager on Portland to reach the 2021 NBA Finals.

Charles Barkley is looking to earn some serious Dame D.O.L.L.As.

On Tuesday’s opening night edition of TNT’s “Inside the NBA”, the Chuckster — while announcing his partnership with FanDuel — placed $100,000 on the Portland Trail Blazers to win the Western Conference in 2020-21.

At the time of the bet, Portland had +2800 odds (per FanDuel), meaning Barkley would earn $2.8 million if Damian Lillard, C.J. McCollum, and co. can prove to be the best in the West this coming spring.

Portland advanced to the conference finals in 2019, only to be swept by the Golden State Warriors. Last season, an injury-depleted Blazers squad limped to a 28-37 record pre-hiatus, but found a groove in the bubble with a healthy Jusuf Nurkic, going 7-2 in mostly “must-win” seeding games. They ran out of gas against the eventual champion Los Angeles Lakers after winning Game 1, falling in five games.

Will Charles Barkley’s bet on the Trail Blazers pay off?

Barkley has shown outsized faith in the Blazers before. Before the Restart, he dubbed the Blazers as a sleeper title contender on ESPN’s “Get Up“. Coming off the seeding games, he picked Portland to upset the Lakers (whoops).

In March 2019, Barkley picked Portland to win the West before their conference finals run.

Evidently, Chuck has not lost his faith in Rip City.

Blazers GM Neil Olshey was busy this off-season as the franchise looks to return to their 2019 success and maximize the rest of Lillard’s prime. Olshey brought back Rodney Hood and Carmelo Anthony, traded for Robert Covington and Enes Kanter, and signed Derrick Jones Jr. and Harry Giles.

As Barkley explained, those moves — combined with a presumably healthy Zach Collins and Nurkic for a full season — is why he’s betting on the Trail Blazers to reach its first Finals since 1992.

(In Barkley’s defense, the odds are admittedly not terrible here, considering the talent in the Blazers backcourt, their potential depth, and playoff experience.)

The long-shot future may be Championship Chuck’s first bet with FanDuel, but he’s far from a gambling neophyte. In an interview with ESPN in 2006, Barkley estimated that he’d lost over $10 million at the casino over the years, including $2.5 million in a six-night stretch.

"“It’s a stupid, bad habit. I have a problem,” Barkley said. “But the problem is when you can’t afford it. I can afford to gamble. I didn’t kill myself when I lost two and a half million dollars. I like to gamble and I’m not going to quit.”"

Fortunately — for the sake of his own wager — Chuck didn’t “GUARANTEEEEE” this one.