The New York Yankees enter another offseason facing familiar questions about how to build a roster capable of making a deeper postseason run in 2027.

While general manager Brian Cashman has several decisions to make regarding the team's existing roster, New York also has an opportunity to address some of its biggest weaknesses through free agency.

Of course, signing a few players won't solve everything. The Yankees still have holes to address in the infield and outfield, and trades will likely be necessary to construct a more complete roster.

But if New York can land these four free agents, it would be a pretty successful start to the offseason.

David Bednar

Of all the decisions facing the Yankees this winter, bringing back David Bednar should be among the easiest.

The two-time All-Star has been everything New York could have hoped for since acquiring him from the Pittsburgh Pirates at the 2025 trade deadline.

Bednar helped anchor a bullpen that finished 2026 with the lowest ERA in baseball, converting 35 of 39 save opportunities while recording a 2.47 ERA, 1.04 WHIP, and 76 strikeouts across 69 1/3 innings.

Since arriving in the Bronx, the 32-year-old has registered 45 saves with a 2.39 ERA in 86 appearances.

The Yankees extended Bednar the one-year, $23.15 million qualifying offer on Monday. But given his performance and status as one of the top relievers available, he'll be looking for a multi-year commitment.

And New York should be willing to make one.

With several bullpen arms potentially departing, allowing Bednar to walk would create an unnecessary hole in the ninth inning. The Yankees already have a proven closer, and finding another one capable of replicating his production could prove considerably more difficult.

Ryan Jeffers

The Yankees entered the 2026 season needing a right-handed catcher to complement Austin Wells, and that need hasn't disappeared.

Wells showed encouraging signs down the stretch, hitting four home runs in his final 10 regular-season games before posting a .761 OPS in the postseason. His defensive contributions and familiarity with New York's pitching staff shouldn't be overlooked, either.

However, the Yankees need more offensive production behind the plate than they received from backup Ali Sánchez, who hit .244/.275/.302 with a .577 OPS in 51 games.

Ryan Jeffers would provide a substantial upgrade.

The 29-year-old hit .256/.353/.461 with 14 home runs, 56 RBIs and an .814 OPS for the Minnesota Twins in 2026, offering the right-handed power and on-base ability New York has been missing at the position.

There's one potential complication: Jeffers could attract interest from teams willing to offer him a starting role rather than a traditional backup job.

Signing him would likely force the Yankees to reconsider how they distribute playing time behind the plate, particularly with Wells still under team control.

But competition isn't necessarily bad, especially for a team looking to improve its offensive consistency. If New York has an opportunity to add a catcher with Jeffers' production, it shouldn't pass simply because Wells is already on the roster.

If the Yankees can't convince Jeffers to accept a shared role behind the plate, Carson Kelly would be a logical alternative. AsYankees on SI's Joe Najarian recently noted in his ranking of the Yankees' top free-agent targets, Kelly's success against left-handed pitching makes him appealing as a complement to Wells. The veteran hit .298/.375/.496 with a 143 wRC+ against lefties in 2026, making him a potentially more practical fit for a catching platoon.

Teruaki Sato

If the Yankees want a significant offensive upgrade this offseason, Japanese slugger Teruaki Sato might be one of their most intriguing options.

The 27-year-old is coming off a remarkable 2026 campaign with the Hanshin Tigers, capturing the Central League Triple Crown after batting .306 with 39 home runs and 106 RBIs.

Sato, who also hit 40 home runs in 2025, would offer New York a potential long-term solution at third base, a position that has lacked consistency for years.

His arrival wouldn't come without complications, however.

The Yankees acquired Ryan McMahon from the Colorado Rockies in 2025, and signing Sato to play third base would likely require New York to explore trading McMahon, particularly given the club's existing infield uncertainty.

There are also legitimate questions about how Sato's offensive production would translate against major league pitching and whether third base will remain his long-term defensive home.

Perhaps the biggest obstacle, though, is timing.

Sato was officially posted on November 1, opening his 45-day negotiating window. However, as the expiration of MLB's current collective bargaining agreement approaches, the possibility of a lockout has introduced additional uncertainty surrounding his signing timeline.

With the current agreement set to expire in early December, the Yankees would be wise to pursue Sato immediately rather than risk having negotiations interrupted by a work stoppage.

There will be competition for his services, but adding a player with his power and upside could give New York the kind of offensive boost it has been searching for.

Adrian Morejón

Even if the Yankees manage to retain Bednar, strengthening their bullpen should remain a priority this offseason.

New York finished 2026 with baseball's best bullpen ERA, but much of that success depended on a handful of reliable arms, particularly Bednar, Brent Headrick, and Paul Blackburn. With Blackburn entering free agency and other potential departures looming, the Yankees can't afford to enter 2027 without additional depth.

Adrián Morejón would be an intriguing addition regardless of Bednar's future. The 27-year-old left-hander emerged as one of San Diego's most effective relievers, posting a 2.83 ERA, 1.08 WHIP, and 107 strikeouts across 86 innings in 76 appearances during the 2026 season.

Morejón combines a high-velocity sinker with a devastating changeup, giving New York another legitimate swing-and-miss option in high-leverage situations. He also allowed just four home runs all season, an appealing quality for a pitcher who would be calling Yankee Stadium home.

If Bednar departs, Morejón could potentially compete for the closer's role, although his limited experience finishing games makes him a less proven option in the ninth inning.

Ideally, though, the Yankees wouldn't have to choose between the two. Bringing back Bednar while adding Morejón would give New York a formidable late-inning combination and much-needed insurance for a bullpen that can't afford to rely on the same few arms for another 162 games.