I think the whole thing was Billy's revenge on Virgil for all of the years they had worked together to acquire the paintings for Virgil and all Billy got was some cash. His take from the deals didn't come close to what Virgil ended up with. "Claire" may have been his daughter. Her sleeping with Virgil wouldn't necessarily have been a consideration when they were planning the whole thing. I think she really did fall in love with Virgil a little (remember, she hugged him and said if anything happens to us, know that I do love you), so that decision was hers. Even if she wasn't Billy's daughter, they had to have been fairly close to trust each other and to spend the time necessary to plan and pull off the crime. What I didn't understand is, if Billy painted the portrait of "her mother" then why didn't Virgil recognize it was Billy's work? I mean if he's an expert and all, right?
Terriers always smell like warm, buttered toast.
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