(I don't have MLB The Show 20 yet, so this is on 19 and I will see if switching to 20 once I get it fixes the issue) My player has 7 years of MLB service and is eligible to go into free agency. After winning the WS I talked to my agent and pressed a button saying enter free agency. My contract is through 2026, and yet in the offseason I get no offers from any teams and I end up somehow resigned to the same team without choosing to be and in spring training signed for two more years. Does anyone else have this problem/solutions? I fortunately have a save right after winning the WS and right before going into the offseason so hopefully that helps. When I hit "begin offseason" I am immediately resigned for two more years to my current team without being able to go into free agency.
I don't know the answer as I've never gotten up to 7 years with my RTTS players, however I suggest if you don't get an answer here, ask the people on the Operation Sports MLB The Show forum as they seem to have a lot of in-depth knowledge on the under-the-hood stuff in RTTS and Franchise.
I’ve never had that issue though I have purposely went all offseason without signing on purpose to see what would happen and it let me pick any team I wanted for a tryout during spring training; after ST I was offered a contract by that team.