The five questions facing the Yankees this offseason revolve around free agency:
Cole in the stocking?
Regardless of the outside noise relentlessly suggesting otherwise, the Yankees never planned to make a serious run at the top free agents of last year’s class – Bryce Harper and Manny Machado — and never did.
This year’s marquee name is Gerrit Cole. Though the free-agent process doesn’t officially begin until after the conclusion of the World Series, early indications are the Yankees will do more than kick the tires on the potential rotation difference-maker.
Cole, 29, went 20-5 with a 2.50 ERA and 326 strikeouts in 212 1/3 innings this season, including 11-0 with a 1.51 ERA in his last 13 regular-season starts. He struck out 143 and walked 16 in 89 2/3 innings in that stretch. In his last 25 starts, including the postseason, he is 19-0 and the Astros are 23-2.
What to do about Didi?
Two years ago, re-signing Didi Gregorius would have been considered a no-brainer. But the 29-year-old shortstop, a free-agent-to-be, is coming off a disappointing season that was dramatically shortened as he didn’t join the team until June because of offseason Tommy John surgery. Gregorius didn’t look the same in the field and wasn’t close to the same at the plate, compiling a .238/.276/.441 slash line with 16 homers and 61 RBIs in 82 games.
“I don’t even know where I’m going to be at [next year],” Gregorius told reporters after the Yankees' ALCS Game 6 loss to the Astros on Saturday night.
Asked if he wants to stay with the Yankees, he said: “Yes.”
How much the Yankees, who theoretically could move Gleyber Torres to shortstop, want to spend to make that happen is, of course, the question.
What about Dellin Betances?
The 31-year-old righthander, a Yankee since being drafted out of high school in 2006, was poised to at last strike it rich this offseason as a free agent. Instead, he experienced the most frustrating season of his career. He started the season on the injured list with a right shoulder impingement and then suffered a lat strain that kept him out until September. He made one appearance, Sept. 15 in Toronto, and tore his left Achilles when he jumped for joy after recording a strikeout. He’ll pitch somewhere in 2020 and it could be in pinstripes, but he won’t get anything close to the payday he would have enjoyed.
What about the team’s other free agents?
Brett Gardner, Austin Romine, Cameron Maybin, Edwin Encarnacion and Cory Gearrin all are eligible for free agency. Gardner, 36, who hit a career-best 28 homers after signing a one-year, $7.5 million deal last winter, is a clubhouse leader, is popular with the front office and wants to play next season. It wouldn’t be a shock to see him sign a similar one-year deal. Encarnacion, 36, fit seamlessly in the clubhouse after being acquired via trade in June and was mostly productive. If he wants to be back and isn’t looking to score a multiyear deal, that can’t be ruled out. Romine, 30, has been a Yankee since being drafted out of high school in 2007. This could be his one chance to make some money and land a starting job, which won’t happen with the Yankees. Gearrin and Maybin are not likely to return except at bare-bones prices.
Will Aroldis Chapman opt out?
A report in July suggested that Chapman, 31, plans to exercise the opt-out clause in his five-year, $86-million contract, though Chapman and multiple sources shot that down at the time.
“No player makes that decision in July,” one opposing executive said then. “Too many variables [that can change].”
The last pitch Chapman threw in 2019 resulted in the walk-off two-run homer by Jose Altuve in the ninth inning of ALCS Game 6 that ended the Yankees' season, but that shouldn’t obscure how good he’s been. He had 37 saves, one short of his career high, and a 2.21 ERA in 60 appearances this season. Chapman, who by all accounts loves being in pinstripes, has been one of baseball’s most reliable and durable relievers in his 10-year career, recording 273 saves with a 2.23 ERA and striking out 14.8 batters per nine innings. Don’t dismiss the possibility of his deal being tweaked a bit to give him a bit more, but ultimately, the closer is staying put.