Why is Hellmuth checking in the dark?

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What he is saying is that Phil's betting strategy is not to overbet the pot very ofter, if ever. So, him checking is the same as his normal bet, which usually would get called.

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This is because Phil likes to play small-pot poker, not push his edges, not commit too much to any hand, keep players in pots, then complain when they outdraw him or beat him with aggression, usually to his wife or parents.