The labor agreement does not expire until December 1, giving Cashman roughly three weeks to act. Cashman has little time to address New York’s roster concerns before baseball’s labor dispute threatens to freeze negotiations, signings, and trades across the league.

“The time for introspection is almost over… Brian Cashman and his counterparts will convene in Las Vegas this week for the general managers’ meetings,” wrote Greg Joyce of the New York Post.

The general managers’ meetings begin in Las Vegas as clubs prepare for December’s labor deadline. New York finished 2026 with 93 wins, yet Tampa Bay eliminated them in three games. That early exit leaves familiar questions about the lineup, bullpen, defense, and overall roster depth. He should target several roster fits instead of waiting for one major signing alone.

The bullpen is a concern, despite ranking second in baseball with a 3.13 ERA. Six Yankees relievers became free agents, leaving several important late-inning roles unsettled for 2027. Bednar recorded 35 saves and a 2.47 ERA across 69.1 innings for New York. Bednar must decide by November 17 whether to accept their one-year, $23.15 million offer. Paul Blackburn also deserves attention after posting a 1.59 ERA across 85 innings this season. Cashman still needs setup help, left-handed relief, and enough depth to protect leads late.

The infield presents another problem, with Jazz Chisholm Jr. entering free agency this winter. Chisholm’s speed (41 steals) masks his offensive struggles (.711 OPS). McMahon’s .213 average leaves third base wide open. Both departures create a vacuum. The Yankees must decide whether to keep McMahon or find another everyday third baseman. Second base and center field need answers after Chisholm and Grisham hit free agency.

Volpe, Caballero and Spencer Jones offer internal options, but none guarantees an immediate upgrade. Free agency should prioritize contact and defense, including a right-handed catcher behind Austin Wells.

Those roster holes expose offensive problems that became especially clear during the October series. The ALDS collapse told the story: one hit in Game 1, four errors in Game 2, outscored 10-5. Offense and defense both failed when it mattered. Aaron Judge’s absence mattered after injuries limited him to 66 regular-season games in 2026. Giancarlo Stanton barely played after late April, then managed only two postseason pinch-hit appearances.

New York needs more consistent contact, smarter baserunning and cleaner defense alongside its power.

Trading a starter (Weathers, Schmidt, or Gil) could bring an infielder, outfielder, or catcher into the organization. Ryan Weathers, Clarke Schmidt, and Luis Gil could attract interest or potentially shift roles. Trading a starter might bring an infielder, outfielder, or catcher into the organization instead. The 2021-22 lockout lasted 99 days, pushing Opening Day back and eliminating three spring-training weeks. The Yankees still won 99 games in 2022, but Houston swept them in the ALCS.

The lockout remains the biggest threat to the Yankees’ already crowded offseason timetable this winter. Free agents often try to secure deals before a potential lockout, as negotiations can stall once a work stoppage begins. The 2021-22 lockout froze transactions for 99 days, pushing many major signings into a brief post-lockout rush, although it did not necessarily reduce contract values.

The current agreement expires on December 1 at 11:59 p.m. Eastern time in 2026. If talks fail, owners are expected to lock out players beginning December 2. Cashman cannot assume rivals will wait, especially with similar needs across baseball this winter. He must use these meetings to set priorities and move before the market closes.

How can the Yankees solve their team problems?

The New York Yankees have a major offensive problem to solve before the 2027 season begins. Their pitching staff finished with baseball’s best 3.23 ERA, but their hitters struggled throughout 2026. New York ranked 26th in batting average (.235), 29th in hits, and 24th in OBP (.311). That weakness became even clearer during the ALDS, when Tampa Bay swept them in 3 games. The Yankees allowed 10 earned runs over the 3 games but scored only 5, showing how much their offense let them down. Now, the organization appears ready to address those problems by making important changes.

The first signs of change involve Jazz Chisholm Jr. and Trent Grisham, who could leave this offseason. ESPN’s Jorge Castillo reported that both players are “as good as gone” after disappointing offensive seasons. Chisholm finished with a .231 average, 19 home runs and 55 RBIs across 137 games. Although he stole 41 bases, his production at the plate remained inconsistent throughout the season. Grisham also struggled, hitting .211 with 18 home runs and 59 RBIs across 121 games.

Neither received the $23.15 million qualifying offer, which the Yankees instead extended to David Bednar. The closer recorded a 2.47 ERA and converted 35 of 39 save opportunities across 64 appearances.

However, moving on from those players will not address every weakness within New York’s infield. Ryan McMahon hit .213, with 11 home runs and 41 RBIs across 124 games. His struggles have made third base another position the organization needs to reconsider.

YES Network’s Jack Curry reported that the Yankees respect McMahon but recognize third base needs improvement. Second base also needs attention, particularly with Chisholm potentially departing this winter. Anthony Volpe hit .265 in September, while Jose Caballero finished with a .231 average. Both could provide valuable depth, but neither offers a convincing everyday solution right now. Catcher Austin Wells adds another concern after hitting .186 with 14 home runs across 122 games.

The Yankees could address these weaknesses by pursuing 3 established players in the upcoming free-agent market. Luis Arraez is an option at second base after hitting .310 across 151 combined games. He also improved defensively, making him a particularly interesting option for New York. Spotrac projects a 3-year, $54 million contract, giving the Yankees a potential long-term solution.

At third base, Alec Bohm could provide another opportunity after a disappointing 2026 season. He hit .249 with 15 home runs and 88 RBIs across 155 games. His career .273 average suggests he could offer more consistent production than McMahon.

Behind the plate, Ryan Jeffers could become another important addition for the Yankees this offseason. He hit .256 with 14 home runs and 56 RBIs across 92 games. His .353 OBP also offers a noticeable improvement over Wells’ .292 mark in 2026. Spotrac estimates a 3-year contract worth approximately $37.5 million for Jeffers. Together, these additions would give New York stronger options across 3 important positions. The Yankees already have the pitching strength, but their lineup needs similar attention.

If they make these moves, New York could enter 2027 with fewer offensive weaknesses.