Damon. First, the Yankees are a more hated rivalry than the Heat. Second, Ray never commented about how signing with the Heat would be a slap in the face to the fans, and never stated that he wouldn't do it (unlike Damon).
Last, the Red Sox didn't try to trade Damon multiple years, and then go out and sign a replacement that would eat up a lot of his playing time in free agency. I still hope Ray comes back, but if he leaves, I can't really fault him.