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Yeah, it's not realistic and I don't think I'd do it myself. Not sure under what circumstances I would give out an 8-year deal to a 27 year-old.
Buuuut, I actually have gotten close. After the 2013 season I re-signed Jacoby Ellsbury to a 4/40 deal, and then traded him next offseason. I did it because his scouted rating at CF dropped suddenly from a 7 to a 3, making him basically unusable (started as the Sox in 2012, so Carl Crawford's truly unmoveable deal is manning LF).
I justified that because of the sudden ratings drop, the fact that it was 'only' 3/30 left and because it's believable that some other team might differ in their opinion of Jacoby's defensive chops (dealt him to Detroit for a C-prospect, and the Tigers don't seem to care too much about defense).
I'm slightly ashamed of that, but I think moving a seven year overpay would be a step too far. It bothers me when I see stars on big contracts dealt between AI teams (Fielder, Cabrera and Darvish have all been flipped in my game), so I'd prefer not to contribute to that issue.
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