A muscle bound giant of a man, Owlbear appears to be a mentally handicapped individual that Mister Plugg keeps as a 'pet' and orders to fight others. From evidence during the time he was brought out of his cage above deck for the fight against Lily, it appears that Mister Plugg or the crew tars and feathers the man to dress him up as his namesake.

After trying to run from the fight, only to be pushed back in by the crew, Owlbear lost the fight against Lily when he was laid out by her with a decisive punch, an outcome Mister Plugg was none to happy with. He has since been dragged back to his cage and locked up.

Since then, both Anastasia and Lily have sneaked into the area where Owlbear is kept locked up at night and have offered him fresh crabs (his favorite food) and talked with him, granting him a better disposition to the party as a whole.

They found out from him that he sees himself as nothing more than a pet of Harrigan, wanting to please his 'Master' in any way by following his orders. Both Lily and Anastasia have tried to convince him otherwise, and he seems to be warming up to the both of them.

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