#4 vs. Kamaru Usman
Of all the fights on this list, we were probably closest to seeing this one. Had Askren been able to overcome Jorge Masvidal at UFC 239, rather than being knocked out in five seconds flat, the likelihood is that the UFC would’ve granted him a shot at their current Welterweight kingpin Kamaru Usman. And boy would that have been a fascinating fight.
Usman defeated Tyron Woodley for the title this past March – coincidentally on the same show that Askren made his UFC debut with a win over Robbie Lawler – and currently boasts a record of 15-1. He’s the most feared 170lber on the planet today, purely because thus far into his UFC career, nobody has been able to do a thing to prevent his powerful grappling game from allowing him to dominate inside the Octagon.
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But despite showing almost superhuman strength at times, Usman’s record as an amateur wrestler actually pales in comparison to that of Askren; ‘The Nigerian Nightmare’ won an NCAA wrestling championship as a collegiate athlete – but only at the Division II level, whereas Askren won two titles in Division I.
Could Askren have been the one to impose his own wrestling game on Usman? And if that were the case, how would Usman have reacted to being taken down in the Octagon for the first time? We’ll never find out now that Askren has retired, but it’s hard not to wonder what might’ve been had he avoided that flying knee from Masvidal!