That's according to Tristar Gym trainer Firas Zahabi, who served as the main coach for UFC legend Georges St-Pierre in his glittering fighting career.
Paul, who has competed professionally twice, will enter the squared circle again against Askren on 17th April at the Mercedes-Benz Stadium in Atlanta, Georgia.
And ex-Bellator and ONE Championship welterweight champ Askren, who retired from MMA in 2019, managed to rattle the 24-year-old American YouTuber by talking about his older brother, Logan Paul.
Now, Zahabi believes that Askren will emerge victorious in the fight as he expects him to "dirty box" Paul.
Speaking on the Tristar Gym YouTube channel, he said: "I think Ben Askren wins.
"Here's why, I saw Jake Paul's last fight, he'd knocked out some guy with a couple overhand rights, stunned him a few times, dropped him. But here's where Jake Paul -- I don't think he knows what he's getting into.
"Number one, Ben Askren is a wrestler, yes and his forte is not striking, we all know that. He's not the greatest striker. But he's been in there with killers. He's been in there with like legitimately dangerous human beings.
"Robbie Lawler, Douglas Lima -- I can go on and on, the list is super long. He's been in there with real killers, and I know he didn't use boxing, but he took shots from these guys... it was some serious shots. Ben Askren never wavered.
"The computer was still working, he didn't panic. He's a true competitor.
"He's been training in MMA, he's been learning how to strike. Let's call it 15 years, he's been striking -- let's call it 10 years, let's be very reserved here.
"It's not only boxing offense that's the issue. I guarantee you that he takes a shot better than Jake, I can guarantee you that, I'm guaranteeing you that right now.
"So Jake's going to go in there, and in the first two, three rounds he's going to be dancing around and he's going to jab Askren. He's going to look alright, he's going to look good.
"Askren's going to hit him back and it's going to be a give and take. But here's what Jake doesn't know, Askren has proven that he's got an incredible chin."
Zahabi has suggested that he wouldn't be surprised if Askren is "disqualified," saying he "will be all over" Paul in the fight.
St-Pierre's long-time coach and trainer explained: "Ben Askren is going to maul him in the clinch, dirty box him. He's going to get warned by the referee, but it doesn't matter.
"Barring the exception that Askren's chin is finished [after that Jorge Masvidal KO], Askren is going to maul him.
"It's not going to be pretty. It's going to be a dirty fight. It's going to be a seesaw battle a little bit early on, then all of a sudden Jake is going to fatigue and Ben Askren will be all over him.
"He'll throw him on the floor, ragdoll him. Maybe even picks up and slams Jake Paul once or twice. It would not surprise me.
"Ben Askren probably doesn't have a clause where if he gets disqualified, he doesn't get paid. In my opinion, Ben Askren doesn't care if he gets disqualified.
"He's going to pull on his head, step on his feet -- shove him so he's off balance, and it's going to be a mauling.
"How is he going to pick and poke, stick and move and stay away from Askren? Once they lock up, once they lock up, I guarantee you, Jake's battery is going to start to drain."
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