Breaking down issues Yankees must deal with this offseason

As the Yankees head into another long offseason following their ALDS elimination, they’ll once again be looking how to win in October, especially after being knocked about by the Rays and their miniscule payroll.

Instead of facing off against the Astros in the ALCS for the third time in four years, the Yankees’ focus turns to 2021, and though this past season will always be looked at amid the backdrop of the impact of COVID-19, the reality is another disappointing end to a season that began with championship aspirations.

As Gerrit Cole said after his first season in pinstripes ended late Friday night when asked about what changes needed to be made moving forward, “We didn’t reach the goal, so across the board, we need to improve.”

Here are several areas general manager Brian Cashman and his front office will need to address during the coming weeks:

Free agents

DJ LeMahieu

The Yankees got quite a steal when they seemingly came out of nowhere to sign LeMahieu to a two-year, $24 million deal, even though he didn’t have a clear role. He’s been good enough with the Yankees that Aaron Boone said, “he’s on the short list of short lists for being the best player in the sport.’’

Masahiro Tanaka

The seven-year $155 million deal that landed Tanaka in The Bronx from Japan is over. He was quick to decline an opt-out following the 2017 season and seems a strong candidate to return, but his reputation as an impressive postseason pitcher took a hit with two straight duds in these playoffs.

Brett Gardner

Despite rough stretches during the regular season, Gardner again showed his value by being one of the Yankees’ most reliable bats during the playoffs, and it helps that he’s one of the only left-handed hitters on the roster.

J.A. Happ

The lefty had a vesting option for next season that won’t kick in, and Happ had a rough season in The Bronx — from publicly wondering if the Yankees were manipulating his starts to prevent him from reaching his incentives to expressing his displeasure with how he was used in their ill-fated pitching plan in Game 2 of the ALDS.

James Paxton

The injury-prone southpaw never made it back for the Yankees after suffering an elbow injury and hits the open market at an inopportune time.


Boone has a team option for a fourth season in the Yankees’ dugout, and all indications are that he’ll be back, but another October disappointment doesn’t help his cause — especially after he was outmaneuvered by Tampa Bay’s Kevin Cash.


What do the Yankees do with Gary Sanchez? He’s due to get a raise from $5 million in arbitration and is coming off a horrific season in which he hit .147, performed poorly behind the plate despite a new catching coordinator then lost his starting spot to Kyle Higashioka in the playoffs.

Miguel Andujar

Remember him? The Yankees had hoped he could fill a versatile role after losing the third base job to Gio Urshela, but he doesn’t have a position and didn’t hit as a part-time player.

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