Yankees: How to extend their championship window
As for Judge, Sanchez, and Severino, extensions for them would be great for the team but seem to be less likely. They have all established themselves as stars already and because of this, they are poised to get substantial pay raises once they start arbitration following the 2019 season. One benefit for Scott Kingery signing his deal is that he is now guaranteed to receive a life-changing amount of money without the risk of injury or poor performance.
This factor is substantially reduced for the three Yankee stars, as their accomplishments thus far have already guaranteed them life-changing money through arbitration, which rewards players for their performance and even more so when they excel. Judge’s top two MVP finish, Sevy’s top three Cy Young finish, and Sanchez’ Silver Slugger award will all add dollars to their arbitration salaries.
Plus, especially for Judge, all three players have endorsement money to keep them comfortable until their salaries rise. Knowing what kind of monstrous payday awaits them once they hit free agency, it seems less likely they would agree to an extension.
However, the one factor the Yankees do have in their favor is the respective ages the Yankees trio will be once free agency finally arrives. Will Judge be the same player he is now when he’s 31 years old? Will Sanchez still be a viable catcher when he’s 30? Will Severino’s arm hold up after logging so many innings?
These are all questions the Yankees should leverage in negotiations, especially given the hesitancy of front offices across the league to give out huge deals to players past their prime.