Re: I should have just pushed all-in pre-flop right?
His range should be extremely wide here, any 2. Calling here says you might have a good hand but are not willing to risk going in when there is 1 very short stack, and the other guy ain't to healthy either. You DON'T want to be called here, which is why you push preflop (to maximise folding equity). I really don't think this is a situation to get tricky, but to play it straight and let him know.
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