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I always try to extend my players I want to keep before they go free agent. I also try to extend players that are going to get fat raises in arbitration. You can save a lot of money by doing this. If you let them hit the free agent market their asking price starts at ridiculous and goes up from there. I have yet to actually sign a big free agent in my game because they will hem and haw for months on end and then sign with a AI team for way more money than I am willing to give them. If you don't think you can sign them due to cost or the fact they are just plain jerks when you try, then trade them and at least get something out of the deal.
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