Rick Porcello (Free Agent after 2019)
Rick Porcello has won the Cy Young, but ever since has been a mediocre pitcher that hasn’t had a great impact in his club winning games. According to Porcello, he’s “been terrible”.
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Porcello has a career-worst 5.83 ERA and already has 12 losses.
I believe that the new Red Sox GM would be unwilling to give Porcello any longer than a 2-3 year contract, as he is already 30 years old.
If the Red Sox GM were to not sign Porcello, then he would need to fill that spot with another starting pitcher. Obviously, if he didn’t sign Porcello, then he would not be signing any perennial All-Star starter, as they would be commanding a huge amount of money, so a trade would need to occur.
Boston could also play the waiting game with him and his agent. If they don’t want to offer him a lot of money, then they can hope other teams don’t want to either and they can persuade him to sign with them.
All three of these decisions will shape the Boston Red Sox future for years to come and they could go one of two routes: retool and try to go for it in an attempt to come back from a bad season or irritate the fan base and rebuild.