1 free agent from each AL East rival Yankees should target

Changes will be afoot in the Bronx as the New York Yankees look to retool after failing yet again in the postseason. While we focus on the October shortcomings, it can be easy to lose sight of just how difficult making it out of the AL East gauntlet can be.

Three teams — the Boston Red Sox, the Tampa Bay Rays, and, of course, the Yankees — made the playoffs, with the Toronto Blue Jays running out of gas in September. Even the Orioles stuck in the race longer than many would have expected, ultimately passing the Jays for last place. This is the most competitive division in baseball, so when New York is looking at offseason improvements, there's an added benefit to hurting a rival when strengthening the roster.

To that end, we'll take a look at one free agent from each AL East club who could be of use to the Yankees in 2027.

The Yankees should have these AL East free agents on their radar this winter

Boston Red Sox LHP Patrick Sandoval

The Red Sox have shockingly few free agents this offseason, and many like Isiah Kiner-Falefa and Sonny Gray are ones New York should steer clear of. One who could pique the Yankees' interest, though, is left-handed starting pitcher Patrick Sandoval. At face value, New York has no need for another starter, especially one with a 5.12 ERA in 2026. However, there could be more than meets the eye with the 30-year-old.

Sandoval missed the second half of 2024, all of 2025, and the first half of 2026 while recovering from Tommy John surgery and suffering a few setbacks along the way. However, for a time with the Los Angeles Angels, he looked like an up-and-coming young hurler, with a 2.91 ERA in 2022 serving as his crowning achievement. It's possible that he was still knocking off some rust this year after such a long layoff.

There are also indications that the lefty's performance was better than it seemed. He posted a decent 22.7% strikeout rate. He also did a great job limiting hard contact, recording a 34.6% hard-hit rate and an average exit velocity of 87.5 miles per hour. Those marks were 78th and 77th percentile performances, respectively. There's a reason the Red Sox essentially paid for his TJ rehab with a two-year deal, after all.

With Ryan Yarbrough set to hit free agency, Sandoval could be a replacement in the swing-man/long reliever role. The Yankees could also roll the dice to see if he could become a left-handed version of Paul Blackburn. Finally, adding him to the roster could help facilitate a trade from their starting pitching depth to fill a hole elsewhere.

Baltimore Orioles RHP Andrew Kittredge

New York's bullpen is going to need a lot of love this winter. David Bednar, Paul Blackburn, Tim Hill, John Schreiber and Ryan Yarbrough are all free agents, and the group lacked depth even when those arms were in tow. On top of that, Fernando Cruz's partially torn UCL will likely turn him into a non-factor (or a severely bold question mark) in 2027.

Orioles right-handed reliever Andrew Kittredge isn't an alternative to re-signing Bednar, nor is he necessarily best suited to be a seventh-or-eighth-inning setup man. What he can be is a reliable middle relief arm. At 36, he's got some mileage, but he still put up a 3.54 ERA over 48 1/3 innings in 2026. That 3.54 ERA is the worst mark he's recorded in a single season since 2019, so he's proven to be a reliable contributor.

Kittredge is a sinker-slider guy, which tends to be Matt Blake's specialty. He'll be relatively cheap and could be a guy with both a high floor and a middle-innings ceiling.

Toronto Blue Jays outfielder Myles Straw

Admittedly, this one requires some help from the Blue Jays, who hold an $8 million club option on Myles Straw for 2027. If they decline it, he could be someone who pops up on the Yankees' radar. Toronto acquired Straw along with $2 million in international bonus pool money in January of 2025 in hopes that the extra funds would help the organization sign Roki Sasaki. Instead, the defense-first outfielder was their consolation prize.

Straw isn't much with the bat. He hit just .241/.304/.342 in 2026 and owns a career .246/.314/.319 line. The appeal he brings is mostly, though not exclusively, tied to his glove. The 32-year-old is a plus defender in center and can also play the corners. He'd give the Yankees a right-handed-hitting complement to Spencer Jones and the rest of the outfield.

Speaking of hitting, one thing that Straw does well is avoid strikeouts. He struck out just 13.3% of the time in 2026, and owns a 17.1% K-rate for his career. He also has speed. His 29.7 feet-per-second average sprint speed ranked in the 97th percentile, and while he didn't run while on the bases in Toronto, he has a 30-steal season and a couple of 20-stolen-base campaigns on his resume.

New York has been rumored to be interested in trading for Washington Nationals center fielder Jacob Young. If he hits the market, Straw checks a lot of the same boxes and could be had for just money, allowing the Yankees to hang on to those prospects or move them in a different deal to fill another hole. Of course ... there's a personal history here between Straw and the home fans that would need patching up.

Tampa Bay Rays RHP Nick Martinez

The Rays and Nick Martinez have a mutual option for $20 million for 2027. Those sorts of options rarely ever get picked up by both sides, and after Martinez's playoff run, it's fair to say that the 36-year-old probably wants to test the open market.

The Fordham University product likely prices himself out of what the Yankees would feel comfortable paying for the role they'd ask him to fill. While he made 31 starts in Tampa, the majority of Martinez's career has been as a jack-of-all-trades type of pitcher, filling numerous bullpen roles and swinging into the starting rotation when needed.

That kind of versatility has a ton of value for a pitching staff. Much like adding Sandoval, Martinez would allow the Yankees to reallocate other assets via the trade market to solve other needs. The problem will be the price, but if Brian Cashman is feeling bold, Martinez would be a great pickup.

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