No New Shortstop For Yankees; Benintendi, Taillon To Return
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Benintendi, Taillon want to stay, Yankees may not sign a free-agent shortstop

John Allen by John Allen
May 16, 2025
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After the Astros swept them in the ALCS, the Yankees have a lot of questions as they head into the off-season. The team has already said that Aaron Boone will be the manager again next year, but the players Boone will be in charge of could change a lot. Over the next few months, the news will be dominated by Aaron Judge‘s contract bids. However, there are plenty of other interesting things going on in the Bronx that will be worth keeping an eye on.

The Yankees have eleven players who are about to become free agents. However, it seems likely that they will pick up Luis Severino‘s $15 million team option, bringing the number down to ten. Jameson Taillon and Andrew Benintendi are others who want to stay. Bryan Hoch of MLB.com says that both have expressed their interest to play for the Yankees again. Most soon-to-be-free agents say they’re open to or willing to talk about going back to their old team. The fact that Benintendi and Taillon have said isn’t a big surprise, though, because the Yankees could re-sign both of them.

Taillon was bought from the Pirates before the 2021 season for minor leaguers Roansy Contreras, Maikol Escotto, Miguel Yajure, and Canaan Smith-Njigba. Taillon is no stranger to injuries. He’s had Tommy John surgery twice and a hernia surgery in 2015. He’s also a cancer survivor, having had surgery for testicular cancer in 2017. Because of his second Tommy John surgery, he missed the 2020 season, so the Yankees limited his workload in 2021. Even though he made 29 starts, he only threw 144 1/3 innings. But in 2022, he got better and pitched 177 1/3 innings of 3.91 ERA ball. Taillon has never been a big strikeout pitcher, and he struck out about a fifth of batters this season, but he had great control, walking batters only 4.4% of the time. He is a little vulnerable to the long ball, but overall, Taillon is a reliable mid-rotation arm who could help many teams in the future.

The Yankees could be one of these teams. At the top of the rotation, Gerrit Cole and Nestor Cortes will be back, and Luis Severino should round out the first three spots. Then there are some question marks. Domingo German pitched 72 1/3 innings with an ERA of 3.61, but his FIP was 4.44 and the speed of his fastball went down a bit in 2022.

Frankie Montas struggled in his first eight starts before going on the disabled list for the rest of the regular season. He came back for the playoffs but only pitched one inning. Montas has a good track record as a mid-rotation pitcher, but in New York, he had an ERA of 6.35. He struck out a lot less with the Yankees—just 17.8%, which is 8% less than the first half of the season with Oakland—but he walked a little more. The Yankees could use either German or Montas to fill out the rest of their rotation, but since both of them have some questions, Brian Cashman’s front office might be more interested in Taillon’s reliability to solidify the back end of the rotation.

Benintendi was traded to the Yankees at the trade deadline from the Royals. In exchange, the Yankees sent Chandler Champlain, T.J. Sikkema, and Beck Way to the Royals. With a slash line of .320/387/.398 in Kansas City, the 28-year-old was in the running for the batting title. He only got two hits in his first 25 at-bats, but he eventually found his groove and hit .303 for the rest of the season. But a broken hamate bone kept him out of action for almost all of September, and he didn’t come back for the playoffs. The Yankees got Benintendi because he is a left-handed contact hitter who will help balance out their lineup, which is full of power hitters, and because he plays strong defense in left. When he was healthy, he did exactly that, so he should have no trouble finding multi-year deals when he becomes a free agent.

Of course, Aaron Judge is the Yankees’ top priority in the outfield, but the team would do well to bring Benintendi back to play left. In the left field in 2022, the team used ten different players. None of them played in more than 55 games there. Aaron Hicks got most of the playing time, but he didn’t do very well, and now that he’s 33, he’s showing signs of getting worse. Down the stretch, the team turned to rookie Oswaldo Cabrera. Even though he had been an infielder in the minor leagues, he did a good job. In 44 games, he hit .247/.312/.429 and played great defense. Depending on what else the team does, they may want to keep Cabrera on the bench as a utility player and bring back Benintendi as their everyday left fielder.

The Athletic’s Jim Bowden says that the Yankees are giving signs that they won’t be looking for a top shortstop this winter. That’s not surprising, since the team chose to trade for Isiah Kiner-Falefa instead of Corey Seager and Carlos Correa last winter. Fans didn’t like Kiner-Falefa, but the move was made so that Oswald Peraza or Anthony Volpe, two of the Yankees’ top prospects, could take over in the long run. Peraza did well in a few September games and made the playoff team. It seems likely that one of these three will be the Yankees’ starting shortstop in 2023.

What do you think? Leave a comment below.

Tags: New York YankeesAndrew BenintendiJameson Taillon
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