[sy_or_bust]

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I'm assuming the players in the big game are solid enough to fold a lot of hands for two bets cold. The crux of the play is the fold equity his raise generates from the players in the middle and also the button.

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I'd be careful about this. It's more likely that these players are good enough to do the opposite - call 2 cold with 'mediocre' hands, understanding exactly what is happening to them a fair % of the time in a 4-way raised pot. The DN analysis linked even estimates that either he or Grey will call 2 cold ~50% of the time - fairly staggering. Grey did call - getting ~6:1 for high with a gutshot, one pair, and a backdoor flush draw.

To make the raise Greenstein did, you have to assess the situation in a completely different way. The Button needs to be betting a huge range of hands, and your raise needs to make it heads-up (or win the pot outright) a much larger % of the time. This is a huge discrepancy, so it is logical that one would call the other's play non-optimal in this spot. Without knowing nearly enough about all the players and head games at this level, I wouldn't delve too deeply into the play here - little of it will apply to small/middle limit O/8, IMO.