The Yankees and general manager Brian Cashman have been forced to shift into offseason mode following Friday night’s ALDS defeat at the hands of the Tampa Bay Rays.
Nobody knows more than Cashman does how impatient Yankee fans can get, and without a World Series appearance since 2009, there’s no doubt there are some anxious members of the fan base who will be closely watching every Hot Stove decision.
Here are three questions the Yankees need to answer as they look ahead for the 2021 season.
Is Gary Sanchez the starting catcher?
Sanchez came into 2020 with renewed expectations after an All-Star season in 2019. He rebounded from a brutal 2018 season to mash 33 home runs with an .841 OPS, and though his defense remained a question mark, there was hope he could finally right the ship on that side of things. But even if he’s simply average defensively, his superior offensive production would more than make up for those shortcomings.
That plan all came crashing to the ground in the shortened season. Sanchez spent much of 2020 with the worst batting average among qualified hitters in baseball. He struck out in more than a third of his plate appearances (64 Ks in 178 PAs) and finished the season with an abysmal slash line of .147/.253/.365.
Meanwhile, Kyle Higashioka entrenched himself as Gerrit Cole’s personal catcher, but also started in two of the other three ALDS games in which the Yankees’ ace did not pitch. Higashioka homered in Game 1 and had four hits in 14 postseason at-bats.
And of course, the possibility of signing J.T. Realmuto also looms, though SNY’s Andy Martino reports the Yankees are unlikely to be big spenders this offseason. But it is the Yankees, after all, and acquiring a high-end talent in free agency is never totally off the table.
Sanchez made $5 million this year and has two more years of arbitration eligibility before becoming a free agent following the 2022 season. He’s been in the organization since signing as an international free agent in 2009, but have the Yankees finally seen enough from him to cut bait? His trade value will be at an all-time low and despite a poor season, his salary is unlikely to go down in arbitration. The Bombers may just have to cross their fingers and hope for another rebound season from Sanchez.
Which pending free agents will the Yankees re-sign?
When the Yankees signed DJ LeMahieu prior to the 2019 season, they surely couldn’t have expected him to be one of the most productive hitters in baseball over the length of his two-year, $24 million contract.
After finishing 4th in MVP voting in 2019, LeMahieu followed that up by leading the American League in batting average (.364), on base percentage (.421) and OPS (1.011) in 2020.
He’s an integral part of the Yankees lineup, and despite what’s sure to be a pay increase for LeMahieu, you’d have to think Cashman will do whatever he can to bring him back.

Giancarlo Stanton has a player option this offseason that he will undoubtedly exercise, so you can expect him back in pinstripes in 2021.
Outside of that, there are some big decisions to be made.
After bringing back Brett Gardner on a one-year deal in 2020, will the Yankees finally say goodbye to their longest-tenured player?
Meanwhile, Masahiro Tanaka, James Paxton and J.A. Happ are all free agents. All on the wrong side of 30, it’s tough to imagine all three – especially Happ—coming back next season. Which brings us to the final question for Cashman to answer this offseason…
Do the Yankees have enough starting pitching?
Yankee fans will be debating the decision to go with a piggyback option of Deivi Garcia and Happ on the mound in Game 2 of the ALDS for a long, long time, but their dearth of starting pitching somewhat forced their hand. Cole and Tanaka were the foundation this season, but Paxton got injured again, Jordan Montgomery struggled at times and the Yankees struggled to find a solid five-man rotation.
Assuming Garcia will become a full-time starter in 2021, where does that leave the rest of the starting rotation? Even if Tanaka comes back, is that enough to round it out? With only 60 games this season, the Yankees didn’t much of a look at Clarke Schmidt, who pitched in just three games in 2020.
There are plenty of options on the free agent market to try to fill out the back-end of the rotation. Pitchers like Jake Odorizzi, Mike Minor and Robbie Ray are all available at what would likely be an affordable price.
While it’s again unlikely the Yankees go big in the free agency market, the perpetually online Trevor Bauer hinted on Twitter earlier this week that he might be interested in heading to the Bronx, though he shouted out some other teams, as well.. He’s said in the past that he plans on pitching on one-year deals for the rest of his career, so perhaps the Yankees would be interested in a short-term investment?
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The Rays cemented their spot as the class of the American League this season, finishing with the best record and then going on to eliminate the Yankees in the playoffs. Now, Cashman will need to make some improvements as they look to reclaim their spot among the AL’s best.