I feel like Ben suffered from the Kevin Lee syndrome, in that he has some big strengths, but he thinks he's way better than he really is, and so either didn't take his opponenets seriously enough, or didn't prepare/train to maximize his potential.
I bet on Masvidal to win by KO, but Askren could very well have held him down like he did to everyone else. In his mind Masvidal posed zero threat, and he paid for that.
He had ways to beat Maia too, but his pacing wasn't good at all, and he engaged Maia too much on the ground, which to me showed he either overestimated his grappling, or underestimated Maia's.
As strange as it sounds, for all his 'intelligence' talk, my impression was that he actually has very bad fight IQ, which in a way might be what Cormier jokingly meant by 'doesn't know how to fight'.