[skp]

Chicago Pro's play:

I think that his play was fine so long as he doesn't always play it this way i.e. now and then, he needs to shed the rope-a-dope and checkraise somewhere. Note betting out on the river after you have played rope-a-dope is a better play when your opponent had raised in a steal position. Here, that was not the case. Chicago raised UTG and Roy 3 bet. He certainly has a legit hand which includes AK. So, Chicago's checkcall on the river is also fine.

Roy's play:

The better play is for Roy to check KK on the turn. BTW, if the flop was A53 for example, he may also want to check QQ. I mean, how can the other dude call his flop bet with a King? With JJ, again, he might want to consider checking the turn as there is little danger that Chicago called the flop bet with a King or Queen in his hand without an Ace. But a turn bet might be supportable if Chicago would fold KK or QQ i.e., given the Ace on the board.

As for Roy's bet, it's not entirely bad either. Perhaps, he told himself that "if Chicago raises, he has an Ace for sure and I can lay down" or that "Chicago would have raised for sure on the flop if he had an Ace and that he is capable of calling me twice more with some lower pocket pair".

But on balance, Roy should probably check KK on the turn.