[soah]

The button played the hand poorly. He gave away his hand without charging people the proper price to draw out against it, and still went to the felt with it on the flop.

With regards to check-raising, I would be more inclined to do that against someone who had open-raised, especially from a later position, since they would presumably raise with many hands other than a big pair. Check-raising could win you some extra money if they choose to bet an unimproved AK (or worse) while they may fold if you lead into them. In this instance the reraiser is extremely likely to have an overpair, and they are unlikely to fold if you bet into them.

Additionally, if you routinely lead out with big hands, you may be more likely to get away with stealing the pot when you flop a draw or a weak made hand. Check-raising as a semi-bluff is expensive, and you hate to check-call with a draw when your opponent may only have ace high.