Surprised people are dismissing Masvidal's chances. His destruction of Diaz aside -- he showed a tremendous ability to pick out and exploit his opponents bad tendencies against both Till and Askren.
He zeroed in on Till's tendency to back up in a straight line while against Askren he exploited Ben's tendency to duck his head for a take-down when pressured. He exploited Till's tendency by not sitting on the jab, instead feinting it, then leaping in with a range finding straight right (instead of throwing it for power) and then clipping him with a left hook. Masvidal had to do this because Till had a significant height and range advantage, which meant that he couldn't close the distance fast enough behind a jab - straight - hook (1,2,3) combo. Smart strategy. And the Askren KO, is pretty self explanatory. Dude duck his head for the takedown when pressured? Flying knee.
These weren't just random KO's by a thuggish street-fighter, they were the fruits of hours of scouting, game planning, and drilling by Jorge and his camp. I don't think there's any doubt that Jorge is a different fighter than he was 2-3 years ago. He's really put it all together tactically, not just walking into the cage looking to punch, kick, and stuff takedowns, but actually putting in the work in camp to walk into the cage with ideas. Dudes gone from just being Game bred -- to having a Gameplan.
Now Usman is the bigger, rangier, stronger man, and is tough as nails. And he's obviously the far superior wrestler, but he's only human. He has tendencies, just like Till and Askren. I wouldn't bet the house against Masvidal exploiting them.
For instance, if i was Usman i would be very wary of exchanging with Masvidal at all with my chin hanging out like likes to do. Sure, Usman has gotten away with it. But he's been feasting on wrestlers and grapplers his whole career. Fact is: he hasn't faced a single top flight stand-up fighter. Not a single one.
I'd be wary of him having fallen in love with his striking, thinking he can go to to toe with Jorge. Again, Jorge is a far superior stand up fighter to the guys Usman has fought. Just look at his resume.
Not saying Usman won't wrestlefuck him, it's possible, but Masvidal is an extremely dangerous fight.