The POOL HALL BOYS are one of the toughest gangs in the game, at least until you get to the high school. Their cues have a long reach and unlike most armed enemies, they don't drop their weapons. If you haven't purchased the Acro Circus yet, this area can be a real pain.
A quick way to beat them is to go up to their leader and propose to him that Pool Halls aren't actually dens of vice and sin, and that in fact their entire gang is nothing but the fabrication of a con man named Harold Hill. Faced with the revelation that they don't actually exist, the Pool Hall Boys will vanish into the ether.
Note that if you use this method, they don't leave any money when defeated, as that would make no sense.
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