[riverboatking]

[ QUOTE ]
His biggest leak IMO is that he has a hard time laying down. I've seen him call off a lot of money with hands like bottom pair.

[/ QUOTE ]

if this is true why are you trying to get so cute?
why not either bet the flop or raise the turn?
either way i don't think it matters, with these stack sizes and your description of the player i think you have to be willing to play for all of his chips in this spot.
so however you end up getting it in is moot.