Jorge Masvidal drops big money on Sean Strickland beating Khamzat Chimaev

Middleweight Khamzat Chimaev will enter the UFC 328 main event title bout on May 8 against former champion Sean Strickland as a heavy betting favorite unless the lines dramatically change.

Most people are picking Chimaev to retain the title but the original BMF titleholder Jorge Masvidal thinks Strickland will hand Chimaev his first career loss. Masvidal is so confident in Strickland winning that he's placed a significant amount of money on it.

"Sean Strickland is different. He's come out to American Top Team a couple of times. I've also seen Sean train. You can take Sean down, and that's very hard, but it's even harder to hold this guy down," Masvidal said on Full Send MMA.

"And I've seen him go with good wrestlers. Chimaev might get a takedown or two on him, but he's going to get so tired because Sean always finds a way back to his feet. He has a system that he follows and he does it to everybody. He gets taken down, he's right back up. And that demoralizes people."

Masvidal isn't sold on Chimaev and pointed to times "Borz" has struggled, or faced adversity in previous fights.

"Chimaev, to me, though he looked great in that DDP [Dricus Du Plessis] fight, I don't think he's all that good, man. I'll be honest with you. I just don't," said Masvidal.

"Look at the [Kamaru] Usman fight. Usman was a 170-pounder. Took the fight on 11-days notice," Masvidal continued while revealing that he saw Usman out late in Miami having a good time two days before accepting the fight.

"I thought Chimaev lost that fight. He won the first round. Look at the tape. He won the first round, lost the second and third. Didn't get more takedowns. Got stuffed up and got punched in the face more. So, I definitely thought Usman won. That's a 170-pounder that's coming off the couch, literally. He's not training. He's not living that life. I know he (Chimaev) went up to 185 and did some big things, but I don' t think he beats Strickland. I don't think so."

"I'm dumping the house on Strickland on that one," said Masvidal. "I'm going to put up 100 bands. And I don't even think Chimaev fights him because they've trained a lot. You see my, on f**king PrizePicks, I put up 100 bands of my own money ... That's how confident I am Strickland beats him."

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This story was originally published April 29, 2026 at 3:27 AM.