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3 Contract Extensions the Yankees Should Still Pursue This Offseason

By Brendan Balsamo

DJ Lemahieu was one of the most under the radar players in all of the MLB in 2019.
DJ Lemahieu was one of the most under the radar players in all of the MLB in 2019. / Bob Levey/Getty Images

Just months away from Spring Training, the New York Yankees are clear favorites in the American League. After winning 103 games and bolstering the only weak part of the team this offseason, their rotation, the Yankees are deemed likely to win 100 games once again with the way free agent acquisition Gerrit Cole will help the team.

Besides homegrown players like Aaron Judge, Gleyber Torres and Gary Sanchez, the Bronx Bombers have other pieces they should really consider investing in for at least a couple more years if they want to build upon his recent string of success.

3. James Paxton

James Paxton was the Yankees most consistent regular season starter in 2019.
James Paxton was the Yankees most consistent regular season starter in 2019. / Elsa/Getty Images

After the gutsy performance by James Paxton in Game 5 of the ALCS, how could you not want him in pinstripes beyond next season? As Aaron Boone made his way out to the mound to pull him with two outs in the sixth inning, Paxton opted to try his luck and urged his manager to leave him in the game. He then ended the inning on the very next pitch. Paxton pitched to a 15-6 record and a 3.82 ERA in 2019. In the final year of his contract, Paxton could earn a big pay day in free agency if the Yankees don't extend him, which would be a mistake.

2. Masahiro Tanaka

Tanaka may not be the best pitcher in the regular season, but he is so valuable in the postseason.
Tanaka may not be the best pitcher in the regular season, but he is so valuable in the postseason. / Mike Stobe/Getty Images

Masahiro Tanaka remains one of the best postseason pitchers of his era. Tanaka's 2019 season failed to live up to the lofty expectations he's set for himself (11-9, 4.45 ERA). Come playoff time, however, Tanaka is a different beast, with a 5-3 record, 1.76 ERA and 0.783 WHIP career. Tanaka's $23 million due in 2020 should come down in his next contract, and Cashman and Co. should aim for a team-friendly deal to keep Tanaka in pinstripes for the foreseeable future.

1. DJ Lemahieu

DJ Lemahieu nearly became a postseason hero for the Yankees in 2019.
DJ Lemahieu nearly became a postseason hero for the Yankees in 2019. / Elsa/Getty Images

The Yankees signed DJ LeMahieu, a player who had previously proved himself in the high altitude in Colorado, to a super-utility role as a stand-in until Didi Gregorius came back from Tommy John surgery. Rather, LeMahieu proved himself and then some, finishing fourth in AL MVP voting, slashing .327/.375./518 with 26 home runs and 102 RBI. DJ kept up this consistency in the playoffs, hitting .325 and nearly saving the Yankees season in Game 6 of the ALCS when he hit a game-tying home run with one out in the top of the ninth off Astros closer Roberto Osuna. Lemahieu outperformed his relatively small two-year $24 million contract he received last winter from the Yankees. With another statistical season like 2019, Lemahieu could earn a nine-figure salary in free agency. That is, assuming the Yankees don't extend him first.