3. Convince Aroldis Chapman to stay
All-Star closer Aroldis Chapman may have given up the home run that ended the Yankees 2019 season, but he remains one of the best ninth-inning men in the league. The 31-year-old has an opt-out in his contract this winter, and he should take it. The six-time All-Star would instantly become the best reliever in this year’s class of free agents and can find himself an additional two or three years of top pay on the open market.
Chapman signed a five-year, $86-million deal to return to the Yankees after helping the Chicago Cubs end their long World Series drought. The contract remains the largest ever for a reliever, and Chapman has lived up to the deal with no further off-field issues. The domestic abuse charges and suspension will always be a part of Chapman’s legacy.
Opting out of two more guaranteed years at $17.2 million per season is a dicey proposition given how the market for elite relievers has slowed down since Chapman and Kenley Jansen signed their $80-million contracts. Still, Chapman has enough leverage that it still makes sense for him to attempt to tack on additional years at the same annual value to his current deal. If the Yankees really want to get crazy, they could target San Francisco Giants closer Will Smith and keep building their mega bullpen with All-Star closers pitching the last three innings of every game.
Without a strong starting rotation, the Yankees have to be assured every lead they carry to the ninth inning will be preserved. Even as he enters his thirties, Chapman is that type of weapon at the back end of a bullpen. He has allowed only three runs in 16.1 innings with 29 strikeouts in the postseason since returning to the Yankees in 2017.