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Harry was the Boss, or head, of the Molehill Mob, one of the many mafia gangs in Gotham City. He aligned himself with the Riddler when the Joking Jackanape sought to sue Batman and make off with treasures from Moldavia.

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Harry tended bar at the What a Way to Go-Go Club, which he and the Molehill Mob ran as a front for their criminal activities. In one case, he served Batman a drugged orange juice to incapacitate him while his moll Molly further distracted the Caped Crusader by asking him to dance.

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