Interesting Hand in the $2k NLH WSP event

[pokergripes]

The following hand came up at my table in the $2,000 buy-in nlh event at the Rio a couple of weeks ago, was wondering what you guys think of the turn play (anyone who already knows how this hand comes out, please don't reveal yet, I've heard a couple of guys I respect argue it different ways so far, and figured it's a close call but wanted to get thoughts without the outcome already being stated):

Full table with $2,000 of chips to start, a few hours in and the table has not been broken, playing $100-200 with no antes.

"Chip Leader" has around $6,500 and is sitting in seat #1 in the big blind, very aggresive player up to that point (almost never traps, just bets out), and also probably the best player at the table.

"Chuckles" is sitting utg in the #2 seat with around $3,100, and is a player prone to make "terrible call on the math" type mistakes when he has a good hand. I've been thinking for more than an hour about how I'm going to take all his chips when he bets at the wrong flop and then calls all-in (he seems kind of surprised to still be there and have chipped up, clearly playing over his head).

I'm sitting in the 6 seat with around $3,500 in chips, above average for the table (probably the 3rd stack or so).

I pick up pocket fives and am the second limper after Chuckles limps utg, small blind folds and Chip Leader checks.

Flop comes down AQ4 of spades, checked around quickly.

Turn is the 5d, Chuckles bets out $800 into the $700 pot, I push, Chip Leader thinks for thirty seconds or so and then calls, Chuckles almost instantly over-calls after that.

So, I'm all in, Chuckles is all in for around $400 less, and Chip Leader has around $3,500 of his $6,500 in the pot.

Thoughts?