5 questions facing the Yankees this offseason

November 2nd, 2019

The offseason arrived about a week and a half too early for the Yankees’ tastes, as their plans to host World Series games at Yankee Stadium swiftly transitioned into planning for 2020.

General manager Brian Cashman will soon head the club’s organizational meetings, in which the focus will be how to upgrade a team that posted 103 regular season victories but was unable to notch the six that separated them from a parade through the Canyon of Heroes.

Here are five questions that the Yankees must tackle between now and February, when pitchers and catchers will once again report to George M. Steinbrenner Field in Tampa, Fla.:

1. Which free agents should they attempt to retain?
Before they get a crack at the open market, a group that includes Cashman’s ‘great white whale’ in Astros right-hander , the Yankees have decisions to make regarding their own impending free agents.

has said that he hopes to return, and after earning $11.75 million for his injury-shortened 2019 campaign, the shortstop is a candidate to receive a qualifying offer valued at $17.8 million for 2020. Are the Yankees comfortable with that commitment? And even if they are, would Gregorius bypass a possible multi-year deal elsewhere?

Other prominent free agents include outfielder ($7.5 million in 2019), right-handed reliever ($7.25 million), catcher ($1.8 million) and outfielder (1.26 million).

The Yankees declined to pick up first baseman 's $20 million option for next season, electing instead to pay a $5 million buyout. Closer could have opted out of the remaining two years and $30 million on his contract, but the 31-year-old left-hander will reportedly remain with the Yankees through 2022 after reworking his contract.

2. Will this be a big-spending Yankees winter?
We’ve seen two offseasons during the Hal Steinbrenner era when the Yankees resorted to wielding their wallet as a weapon. One resulted in a World Series championship (2008-09: , , ), while the other (2013-14: , , ) didn’t work out quite so well.

If the Yankees want to spend on a starting pitcher, this seems to be the winter to do it. In addition to the aforementioned Cole -- a twice-sought Yankees target who could reasonably seek a seven-year deal in excess of $245 million -- the rest of the starting pitching wish list could include , , , , and/or .

According to Spotrac, the Yankees’ 2020 adjusted payroll before adding new contracts is approximately $164.6 million. From that, there will be funds accolated to arbitration-eligible players, perhaps some pre-arb deals and miscellaneous expenses, and it is a safe bet that the Yankees will attempt to stay under the second luxury tax threshold of $228 million.

3. What is the status of their injured players, and how do they keep players off the injured list?
After seeing a Major League-record 30 players land on the injured list (39 stints) this past season, it is reasonable to wonder if the Yankees need to address their training and/or medical staff. Steinbrenner said that the club was investigating the continued injury rash as far back as May. The most troubling aspect was that rehabbing players sustained new injuries -- and Betances being the primary examples. If changes are made, they could happen quietly behind closed doors.

As for the end-of-season injury list, the biggest question was the status of ’ right elbow, but that has been answered. Hicks rehabbed his right flexor strain and unexpectedly played in the ALCS, but after Dodgers team physician Dr. Neal ElAttrache recommended Tommy John surgery, the outfielder will have the procedure. The rehab period will be 8-10 months, meaning he is likely to return sometime next summer.

’s right quadriceps strain and ’s left calf strain should heal over the winter (Tauchman might have been selected for the World Series roster). First baseman believes he can avoid sports hernia surgery, and Betances will be coming off a partial tear of his left Achilles tendon as a potential free agent. Third baseman is expected to be ready for Spring Training, and first baseman is currently playing in the Dominican Winter League.

4. What happened to the ‘Savages in the Box’ during the ALCS?
The Yankees mashed 306 home runs during the regular season and steamrolled the Twins (who hit an MLB-record 307) in the AL Division Series sweep, only to see their bats go cold against the Astros in the ALCS. After beating up and Houston’s bullpen to win Game 1, 7-0, the Yankees scored just 14 runs in the final five ALCS games (12 on homers), going 3-for-25 with runners in scoring position.

Overall, the Yanks were 6-for-36 with runners in scoring position in the ALCS, striking out 64 times. How much credit should be given to the Astros’ pitching, and how much blame should be pinned on the Yankees? Cole and didn’t pitch every single inning.

As much hand-wringing as the starting pitching received, the bats are a bigger reason why the Yanks are home for the Fall Classic. You’d love to have a lineup filled with nine clones, but that’s not reality. Manager Aaron Boone and his hitting coaches, Marcus Thames and P.J. Pilittere, have plenty of time to ponder possible changes.

5. With CC Sabathia’s retirement and Gardner’s possible departure, who will step up as the leaders?
As difficult a moment as it was to witness, there was something appropriate about Sabathia’s final appearance on a big league mound during Game 4 of the ALCS, literally throwing until his body refused to. Sabathia will begin his march toward the Hall of Fame as a terrific Yankee, one who bonded the clubhouse beyond his pitching ability with Spring Training field trips, team barbecues at his Alpine, N.J. home and fantasy football leagues.

Losing that boisterous laugh from the clubhouse creates a void, one that sounded ready to embrace as he candidly discussed falling short in the ALCS. The Yankees haven’t had a captain since Derek Jeter’s retirement, and Cashman has said that he feels no urgency to name another, but Judge may be ready to fill that role regardless of official title.

“We'll be thinking about (losing to the Astros) all offseason, every single day,” Judge said. “That's what's going to fuel me to do whatever I can to put our team in a better position to win. Being a leader of this team, I've got to step up and do something.”