tRaMSt0p

You say he is on his left - which obviously puts you in a tough spot - especially if he is on your direct left.

But as some have said earlier, you do need to make some adjustments to your game while also knowing that he is definitely going to test you early to establish it as his table. 

The first time I open I would be prepared to be faced with a three-bet, and my reaction would be to try a four-bet to show that you aren't easily pushed around. Yeah he might five-bet/jam, but you also have to show that you're not afraid of the other big stack because if you react timidly, then he'll push you around quite a lot for the rest of the tournament and put you in awful spots going forward.

Oh I see ... thanks for clearing that up Grayson!

I think check-jamming the turn isn't the best play against the buttons range of hands with the line he has taken. Against a fairly wide range of hands that include straight draw, flush draw, top pair hand ranges, it's pretty much a flip (although the AK is slightly favored) and he is priced in with nearly all those draws (calling additional 27,000 to win 131,800).

Plus you've also got to consider the middle position player in the hand possibly getting tricky with a check on the turn to entice, but overall I don't love the line.

As played ... check-fold, but ideally either bet smaller on the flop or possibly check-jam semi-bluff.

Grayson ... firstly congrats on another deep Main Event run ... but I was wondering if you could elaborate on your line of "there are lots of players I would happily get it in against here." because you then state "Also, since this is the main event, which is a very unique tournament, a lot of players are not willing to get all-in without a very strong hand."

Getting it with 99 in the ME with a 50bb stack doesn't seem optimal (to me) vs the weaker player pool that the ME comprises of as a combination of experience/good structure/deep stacks will surely give you better spots to take advantage of player mistakes and weaknesses?