It depends on the terms of the trade. If the language is that the Angels have to pay the Rangers x amount at a certain point or points in time, then that's that. What the Rangers decide to do with the money is up to them. If the language is that the Angels have to pay the Rangers x amount at a certain point or points, but it can only used to pay for Hamilton's contract, then the Rangers would probably be obligated to forward that money to Hamilton's new team (or have the Angels send it directly, it doesn't matter). I don't understand your second sentence. If the Rangers can do what they wish with the money (which is possible), it's a trade lever. The team trading for Hamilton would probably want the money, but if the money is not contractually connected to Hamilton, the Rangers are not obligated to do anything with it. If Hamilton puts up a .300/.400/.500 line playing full time in the first half for the Rangers, there may well be a team who would trade for Hamilton whether they'd get the money from the Rangers or not, or at least not all of it. It has never happened before(pocketing the money so to speak) and there is probably a good reason for that. Every time a player like Hamilton comes up in trade rumors they are worth the cheaper part. Not $X to $X depending on how much money is sent over. How do we know he isn't getting two checks in the first place? Getting a check from LA is not going to effect any taxes. It will be the same exact amount if Texas were to pay it.