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Id have given him a 8 year deal with the 7/8 years on team options and a player option for the 4th year on the hope that he opts out when hes 35.
But to be honest 50$ is a lot for any one player at that age. If he was 27 it would be different.
In my experience, as free agency goes along the players demands lower on the free agency player list. But once you open up the contract negotiation page the demand will be different, matching what their highest offer is.
I have also had a player that I was trying to keep for his whole career and he signed with the Dodgers for less years and money than what I offered. Either I was not paying good enough attention to his other offers or he just wanted to leave, not sure.
Anywho, good luck with the situation.
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