After the destruction of Unity, Harold left the Hub and traveled in Texas to Carbon where he had a sexual encounter with Carbon's prostitute, Ruby. He then traveled to the ghoul-city of Los around 2208.
He wanted to have a good time in Los, but the arrival of super mutants and the loss of his hand, toe and eye in the city changed the deal. The Initiate helped Harold to recover his members so he could leave the city before its destruction.