J.D. Martinez (Can Opt-Out after this season)
J.D. Martinez was a huge factor in the Boston Red Sox first and last championship in the Dave Dombrowski era, and if the Red Sox want him to contribute to another championship they will have to comply with his agent, Scott Boras.
Scott Boras is known for having his clients go out onto the market to establish themselves, and while that will most likely happen, recent history is in the Red Sox’s favor (kind of).
Xander Bogaerts signed an extension before this season and he is a Boras client, but I am not sure if Boras and Bogaerts himself were confident in getting more money from the free-agent market than he got in an extension.
The new Red Sox GM would have to give Martinez more money, which ownership might not want, for J.D. to stay because there are teams out there like the Yankees who are more than willing to spend money on a DH.
But the Red Sox may have leverage in this situation because there is a new CBA that will hopefully be settled, and Martinez would be a free agent then if he were to opt-in to his current contract.
The new CBA could be inserting a new rule that lets every team in major league baseball including the National League to have a DH, so Martinez (who would be getting older) would be getting 15 more possible suitors.
If he were to have a new deal restructured with the Red Sox, he might be a free agent before the new CBA kicks in, which might bring down his chances of getting a longer contract.
While Martinez could be in Boston for years to come, it is harder to predict if this starter will be…