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defintiely trade him. get anything you can. dump prospects you don't want and try to get one you do in return.
also, get rid of them before they regress to benchwarmers. otherwise on occasion you will have to cut them. as they age you should be drafting 2-3 potential replacements of varying qualities anyway.
i will start with the shop player around feature and look for a team that stands out by what they are offering. otherwise, i look for a team with a very weak starter at that position (color code in trade screen or various reports). if more than one team fits the description, weigh the different offers.
i am very conscientious of contracts and length. know how long you intend to keep each player. you should always have options planned out years in advance - except in extreme cases of injury, aggressive early aging (rare), or whatever other rare events you can think of.
like ra7c7er said, keep cotracts for 35-36+ short and sweet. overpaying a couple years is better than a complete lump istting on your bench for 20million/year the last few years of a long contract. if they're personality is good i don't mind signing batters in their 30's with option years at age 36 and 37. pitchers are trickier imo. you can make similar guidelines (maybe a year younger). regardless, don't write anything in stone.
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