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Boxy Bennett was a mobster that had power in Gotham. He had confronted Batman a few times. Batman and Harley once went to his club to find the Joker. Harley distracted Boxy by singing a song and Batman with the help of Robin defeated Boxy and his men.
Boxy later had other businesses in Gotham. Harley came to him for help to get her out of Gotham. She managed to convince Boxy by kissing him. But Harley decides to call it off when Boxy wanted use Veronica as a hostage. Batman and Robin arrived and fought Boxy's goons. Boxy then used a delivery truck to chase down Harley and Veronica and ended up in a multi-way crash with Veronica's father's tank, Harvey Bullock's car, and the car Harley was using. He tried to run away but gets captured by Robin who delivers Bennett to the authorities (Detective Harvey Bullock).