
i think the point of pearl was to show that jimmy was trying to connect with somebody whom he felt was more vulnerable than him, or equally vulnerable. in the end, it would always be gillian who held the key to his heart. he obviously struggled with that for his whole life and no matter how much he hated it, it would always be gillian. pearl and california was a glimpse for jimmy of what happiness might be.
(Source: boardwalkempireconfessions)
