That's the Ben Askren, if my knowledge serves, it is against Masvidal. I don't know about Askren specializing in wrestling being a problem, in my opinion it is not a problem, Askren got a 19-2 record to back up his reputation although the Masvidal's knee kick really did him good. No matter what we are hoping for, people that support Jake Paul will buy those tickets and other people who wants to watch it will always buy one, one thing that I hope is that it is for charity.
He's definitely known for his wrestling more than his striking. Ben is a very good wrestler in fact, and that's why hes been in with the big names, such as the mentioned Masvidal. The thing is, he's never been known for his boxing...well that's not entirely true, hes been criticized before for being a one dimensional fighter, and relying on his wrestling. Although, I'm not sure how one can criticize that as wrestling is in fact quite versatile, and seems to be the bane of some of the greatest fighters we've seen in the UFC. Its why I think Khabib has been so successful, other than being a fantastic wrestler himself, some of his opponents were known for their striking ability, and not their wrestling.
However, in this fight it comes down to striking. Ben we know didn't have the best striking in the MMA scene, but that doesn't mean hes going to be bad when compared with Jake. Looking at Jake he has decent technique, but that will go out of the window once hes gets pressured by Ben, because Ben certainly isn't going to be afraid of getting tagged. This pressure is what I think will cause Jake the most problems, since he hasn't really been training long enough to solidify that muscle memory which comes from years, and years of practice, especially when your getting hit back.
In all of his fights, he hasn't been hit back, so we really don't know what to expect once he does. For anyone thinking that Ben simply won't land, I personally think they are overlooking Ben. Ben will catch Jake, and he will be a test despite his apparent lack of ability striking.
For the sake of MMA saving face, I'm really hoping that Ben puts Jake away early in the fight. However, Jake likely won't just disappear, he'll just say he lost to a professional fighter. Its a win, win for Jake. Whereas, all Ben benefits from this is the money involved, which is likely swayed heavily in Jake's favour, since a few other fighters like Bisping were also approached, and made counter offers.