What is the future of Aaron Boone?
Boone’s contract expires after the season, the fourth in four tries in which he led the Yankees to the postseason. While Yankees fans have been critical of Boone on social media, don’t be surprised to see him return. He still is well-liked by general manager Brian Cashman, and indications are managing general partner Hal Steinbrenner, who enthusiastically endorsed the Boone hire four years ago, feels the same. Additionally, Boone remains wildly popular in his clubhouse.
Most significant? The vast majority of people inside the organization know that Boone has little, if anything, to do with many of the decisions he publicly takes the hit for. Many on Boone’s staff have expiring contracts and there could be some cosmetic changes there to appease an unhappy fan base.
Speaking of Cashman, is he safe?
Yes. Cashman, the Yankees’ general manager since 1998, has one year left on his contract, and there are no indications he’s in any kind of trouble. Not yet.
"Brian and I have been doing this a lot of years together," Steinbrenner said during a Zoom news conference July 1. "He's extremely intelligent . . . I think he’s done a good job."
It's a job, however, that doesn’t include a lifetime appointment. When things were at their worst in the early part of the season, Steinbrenner did start asking some pointed questions behind the scenes.
The owner also seemed genuinely caught by surprise during that July news conference when he was asked about the Yankees essentially having abandoned the opinions of their pro scouts when it comes to pretty much all baseball decisions, a process more than a few years in the making and among the worst-kept secrets in the game.
Expect Steinbrenner to address the organization’s overall baseball operations philosophy and approach at length with his GM — sooner rather than later.
Will the Yankees talk extension with Aaron Judge?
Judge, the hands-down face of the franchise, is due to hit free agency after next season. After the Yankees' loss to the Red Sox in the wild-card game, he certainly made it sound as if he’d like those talks to take place.
Steinbrenner’s policy generally has been to not do extensions and to let his employees’ contracts expire first. If there was ever a player for whom he might make an exception, Judge, an organizational draft pick beloved by the fan base and a significant clubhouse voice, would seem to be it.
Though Judge said after Tuesday’s loss that he wants to "be a Yankee for life," he has at times privately expressed discontent with how certain things have played out organizationally. He’s not fearful of going elsewhere, so there’s little chance of a hometown discount.
What will happen at first base?
Anthony Rizzo, an overall effective acquisition at the trade deadline who never was quite the same offensively after coming down with COVID-19, is a free agent and likely won’t come cheap. Still, if the Yankees make one big free-agent expenditure — and there are early indications that Steinbrenner still is committed to staying under the luxury tax threshold (if one exists in the next CBA, whenever that agreement gets reached) — it could be at this position.
Luke Voit has been a popular Yankee since being acquired in 2018 but, despite considerable work put in, he’s still a subpar defender and has been injury-prone. Though popular with his teammates, Voit didn’t do himself any favors with his many "I want to play more" comments after Rizzo’s acquisition.
First base is not considered an area of strength in the Yankees' farm system.
Did Brett Gardner play his last game in a Yankees uniform?
Gardner, a Yankee since being chosen by the organization in the third round of the 2005 draft, answered that exact question after the loss to Boston this way: "I hope not. I hope that I'm back next season."
The Yankees have a team option on the 38-year-old Gardner, who made $4 million this season, and it’s not inconceivable that the club will bring him back.
Centerfielder Aaron Hicks will be a question mark after undergoing season-ending surgery to repair a sheath tear in his left wrist — Mark Teixeira had a similar surgery in 2013 and it took him nearly two years to fully recover — and Giancarlo Stanton, though just fine in the field when given the opportunity in the season’s second half, nonetheless will never be seen as an everyday option there.
Clint Frazier, after a promising start to his Yankees career, has battled a variety of issues that have combined to all but sink his trade value and leave his future in pinstripes murky at best. Joey Gallo, a deadline acquisition who was an upgrade defensively but who continued the feast-or-famine offensive production that has characterized his career since his debut with the Rangers in 2015, is under Yankees control for one more season.