Askren has been one of the best mixed martial artists in recent times, despite having a poor UFC record when he joined the company at 33. In fact, "Funky" was 18-0 prior to his UFC debut against the legendary Robbie Lawler, where he won via bulldog choke in round one. Askren would then be knocked out in the most famous way possible at the hands of Jorge Masvidal, who left him unconscious within five seconds - a UFC record.
Askren's talents in the grand scheme of things as an MMA star cannot be disputed. The four-time All-American won the Bellator welterweight title and defended it a record four times, whilst he also won the ONE welterweight title and defended it three times before heading to the UFC.
However, in all of these 19 wins across an illustrious MMA career, the American never outboxed anybody or looked like a genuine threat in the standup department, leaving all his might down to his sensational wrestling game. Askren does have TKO wins on his record, six to be exact, but each of them have come through ground and pounds and not because of superior boxing skills.
In fact, he was looked at as one of the worst boxers in the UFC at the time of him joining, and his dismal striking display against Maia was evidence of how he might struggle against Paul. Unfortunately for Askren, he really is a poor boxer and clearly has never dedicated time to the trade, but in MMA, this isn't always needed.
This is a close one to call, because at the end of the day, Askren made his MMA debut when Paul was just 12 years old, so naturally, regardless of his boxing skills, the former Bellator champion should have some degree of boxing stored away. It might not be of an elite standard, as he was able to use his superior wrestling more so, but within 12 years of professional MMA, Askren must have something in his locker other than wrestling to put away a man who has just two years of boxing experience.
What will also be a struggle for Askren is the size difference. Once again, just like when Paul fought AnEsonGib and Robinson, the American will come in much taller (3 inches) and heavier, as Askren comfortably fought at 170 lbs throughout his career, whilst Paul weighed in at 189 lbs in his last bout. Again, a boxing federation simply would not have sanctioned this, as Paul is once again choosing the smaller man to build his portfolio, and this is why Askren is the 1/1 underdog.