Meester's parents, Connie and Doug, were involved in a drug ring that smuggled marijuanaJamaica to the United States. Both were arrested for their involvement in the ring and involvement with Heavens Devils, and Connie was released on bail. While out, Connie became pregnant, and once she was convicted, she spent her pregnancy in a Texas state prison. Leighton was delivered in a Texas hospital, her mother was sentenced to ten years in prison. When she was 11, she moved with her aunt to New York City and soon after began working as a model with Wilhemina, booking a Ralph Lauren campaign shot by Bruce Weber and working with then photographer (now film maker) Sofia Coppola.
In Teen Vogue, Meester talked about her past: "I wasn't born in jail; I was born in a hospital. I lived with my mother for a few months in a halfway house, and then I went to stay with my grandmother for a few more before my mom got out. But I had a normal life." from After sixteen months of her sentence, her mother was released and resumed her role in Meester's life.
i just can't take my eyes of her, but when i heard that she actually grew up in a really weird family set up i felt so much respect for her.
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