Upton has hit .250 with 23 homers and 68 RBI with the Rays this year. He also has 30 stolen bases in 128 games. I realize that a .250 batting average isn't that great, but Upton is a 30-30 hitter who plays above-average defense. It's possible that the Rays could let him go this winter, because they have younger players, most notably Desmond Jennings, waiting under him on the depth chart. Anyway, the outfield market this winter isn't that bad, and Upton will be one of the top outfielders out there. You'll definitely see a lot of teams go after Josh Hamilton and Michael Bourn, but Upton might lay low and wait until there is more of a demand for him.
I have a strong feeling that Upton is going to leave the Rays this winter, regardless of whether they make the post-season or not. I personally think that Upton is should get a five year deal worth around $60 million, but we all know that there is that one team every year that will overpay to get what they want. Because of that, Upton could possibly get a contract that would be around $85-$100 million for 5-6 years. Overall, it will definitely be interesting to see how Upton does this off-season, and if he leaves the Rays, I don't think that their fans will be over-ally upset.
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