The Yankees’ Off-Season Puzzle

By John Nielsen

November 13, 2026

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As the Yankees enter what promises to be a complicated offseason filled with moving parts, Brian Cashman faces the daunting task of addressing a multitude of roster issues within an artificially compressed timeframe: The health and advancing age of Aaron Judge; problems left unresolved in 2026, including the need for a right-handed-hitting catcher; positional logjams at first base and designated hitter; self-created free agency vacancies at second base and center field; and the need to upgrade at catcher and third base all demand attention. Add a bullpen demanding significant reinforcements — despite a legitimate surplus of starting pitching — and there is no shortage of work to be done if the club is to position itself for a return to the World Series in 2027. With a baseball lockout certain to begin in less than three weeks, the window for maneuvering is rapidly closing.

Finding the right answers while optimizing the 40-man roster and navigating the constraints and complexities of an unusually challenging offseason will be a conundrum of the highest order. Is Cashman up to the task? His handling of the 2025-26 offseason and the 2026 Trade Deadline offers little reassurance, raising further doubts about his ability to put all the pieces in place — and, critically, to finish the job rather than leave the Yankees with yet another half-completed project.

In 1974, Hungarian architecture professor Ernő Rubik invented a deceptively simple puzzle that by 1980 would become a worldwide sensation. Originally called the Magic Cube, it featured six sides and six colors, with a seemingly straightforward objective: arrange the colored squares so that each side displayed a single, uniform color.

More than 50 years later, the Rubik's Cube remains a formidable challenge, with more than 43 quintillion possible configurations. The difficulty isn't simply moving the individual pieces; it's figuring out how to move one without disrupting the arrangement of the others. Every turn has consequences, and a move that improves one side can complicate the solution elsewhere.

The New York Yankees have their own Rubik's Cube to solve this offseason, with the added complication of a baseball calendar whose deadlines are dictated by the expiration of the Collective Bargaining Agreement in effect since 2021.

The first major deadline — the $23.15 million qualifying offers for 2027 — came and went last week. The Yankees extended just one offer, to right-handed closer David Bednar (1.9 bWAR, 2.61 FIP), who saved 35 games and posted a 2.47 ERA in 2026. Bednar has until November 17 to accept the offer or, alternatively, reject it and enter the free-agent market.

Nine other Yankees from the 2026 roster — four position players and five relief pitchers — became free agents last week without qualifying offers. As a result, the Yankees will receive no compensatory draft-pick compensation, if any of them sign elsewhere. Here's a look at who departed, what they provided in 2026, and the roster needs their departures leave behind:

AGE PLAYER                ROLE/ROSTER NEED     2026 PERFORMANCE

29   Jazz Chisholm        Starting 2b                          1.7 bWAR/97 OPS+

39   Paul Goldschmidt   Platoon 1b/ph v. LHP          1.3 bWAR/111 OPS+

30   Trent Grisham        Starting cf                            0.6 bWAR/95 OPS+

31   Amed Rosario        No Helpful Role?                -0.2 bWAR/88 OPS+

32   Paul Blackburn       High Leverage/Set Up        3.1 bWAR/3.75 FIP

32   John Schreiber      Middle Reliever                    0.8 bWAR/4.62 FIP

34   Ryan Yarbrough     Long Reliever                     0.2 bWAR/3.45 FIP

33   Michael Fulmer      Middle Reliever                   0.1 bWAR/4.34 FIP

36   Tim Hill                  LOOGY/No Helpful Role?    0.0 bWAR/5.93 FIP

While several of these players had their uses and will be missed, none deserved the QO that Bednar got.

The most controversial move was denying Jazz Chisholm his much hoped for QO. Had Jazz put up the 4.1 bWAR that he put up in 2025 or even just the 3.5 bWAR that Trent Grisham put up that same year, he probably would have received the Offer. He fell short of the 50 HR-50 SB season he said he was shooting for in Spring Training. Far short.  While Chisholm's considerable talent was never in question, his consistency, maturity and occasional behavioral distractions became nearly as much a part of the conversation as his sub-par production. From the lollipop episode to numerous ABS challenges run amuck, to raging disputes with umpires on checked swings and his postseason frustration with Aaron Boone platooning him, Jazz too often made himself a distraction. The organization clearly wasn't willing to make the required financial commitment and put up with the nonsense, so the music for Jazz will now play elsewhere. Vaya con Dios, mi amigo! I hope you can find a new home that will allow you to more consistently unleash your great talents.

Trent Grisham had some memorable moments during his three years in New York, but his declining physical skills became increasingly difficult to ignore. Despite the great mustache, questions about his ability to competently cover Yankee Stadium's expansive center-field territory were legitimate. His repeated hamstring injuries further limited his utility. Grisham’s 3.5 bWAR in 2025 provided a useful benchmark for what Chisholm needed to produce to make a Qualifying Offer palatable. But Grisham's 2026 season (0.7 bWAR) tells another story — one about the risks of committing a hefty QO to a player for another year when age and declining performance become increasingly obvious. Taken together, the two Grisham seasons clarify the Yankees' reluctance to extend Chisholm a qualifying offer for 2027. Further, the QO is not simply a one-year financial commitment; it also restricts a club's ability to move on from a player who accepts it. Through June 14, any trade would require the player's consent – effectively granting him a limited no-trade clause – restricting the Yankees' flexibility to reshape their roster during the first half of the season.

I will miss Paul Goldschmidt's still-clutch, if highly situational, bat. Unfortunately, with the roster already jammed-up by the likes of Rice, García and Stanton (whom Cashman insists will be rostered in 2027), there simply isn't room on a four-man bench for Goldy's productive platoon bat against left-handed pitching (.967 OPS), particularly given how ineffective he became against right-handers (.590 OPS). Against LHP, Goldschmidt can still hit like a vintage Aaron Judge. The problem is that he he’s become such a liability against right-handed pitching, it’s impossible to justify the roster spot.

A lot of folks criticized the Yankees' decision to re-sign Goldschmidt last offseason, but his 18 home runs and highly productive May and June (particularly, right after Judge went down) justified the signing and silenced most of those critics. Thanks for your contributions to the team in 2025 and 2026, Paul. I hope your time in pinstripes helps put you over the top in your quest for Cooperstown. His 390 home runs, .375 career OBP and 65.1 bWAR make a compelling case that he belongs there. If Goldschmidt’s career ends here, he will finish remarkably close to another former Yankee corner infielder, Graig Nettles, in several key statistical categories — home runs, RBI and bWAR. Nettles, sadly, came up just a little short of the Hall, despite his 68.0 bWAR. I hope Goldschmidt doesn't.

A couple of other Yankees whose time in pinstripes has clearly run its course are Amed Rosario and Tim Hill. Neither was able to deliver what the Yankees needed most from him in 2026. Rosario, a career .777 OPS hitter against left-handed pitching, managed just a .606 OPS versus LHP this past season. With limited speed and defensive shortcomings at all infield and outfield positions, there is little reason to expect him back.

Hill's decline was equally evident. After dominating left-handed hitters in 2025, holding them to a .444 OPS, he saw that figure climb to .611 in 2026. The long ball became a particular problem. Hill surrendered 12 home runs in 58.1 innings (1.85 HR/9), compared with just eight in 67 innings (1.07 HR/9) the previous season. For a pitcher whose primary value was his ability to neutralize left-handed hitters and keep the ball in the yard, that deterioration leaves the Yankees with little choice but to cut him loose.

The same cannot be said of Paul Blackburn. He was nothing short of brilliant in 2026, somehow producing 3.1 bWAR — the fifth-highest total on the ballclub and easily the best season of his career. There was admittedly a bit of smoke and mirrors involved, given the considerable gap between his 1.59 ERA and 3.75 FIP. Still, Blackburn appeared in 62 games, covered 85 innings, posted a 1.08 WHIP and finished 7-3. While he was never going to receive a qualifying offer, he is one bullpen asset the Yankees should  continue to pursue in free agency, particularly given their current need for reliable late-inning relief. FanGraphs estimates his market value at approximately $6 million on a one-year deal. In my view, bringing back both Bednar and Blackburn should rank among the Yankees' two highest offseason priorities — and that's saying something given the length of their to-do list! While both may have some regression to the mean in 2027, Yankee fans would sleep a whole lot better knowing both leverage relievers are safely back in the fold providing at least a skeletal outline of a competent late-inning relief corps for next season.

Ryan Yarbrough, whose estimated market value is roughly half of Blackburn's, would also represent a reasonably sound reinvestment at approximately $3 million. He could provide long relief, spot or emergency starting coverage, and situational work against left-handed hitters at a bargain price. I wouldn't rule out bringing back John Schreiber or Michael Fulmer, either, provided the price is right. Fulmer made the league minimum last season and remains an ongoing injury risk; Schreiber, according to Spotrac, earned $3.715 million in 2026. Offers of about $4 million for Schreiber and $1 million for Fulmer would be reasonable starting points.

With free agency reducing the 40-man roster to 30, anticipated re-signings of Bednar, Blackburn, Yarbrough and either Schreiber or Fulmer would bring it back to at least 34. The somewhat unexpected addition of infielder/outfielder Marco Luciano to the 40-man roster on November 2 pushes the projected total to 35. These roster dynamics take on added importance with two critical deadlines approaching: November 17, when the Yankees must decide which prospects potentially exposed to the Rule 5 Draft warrant protection on the 40-man roster, and November 20, when they must decide which arbitration-eligible and pre-arbitration players to tender contracts for 2027. Those not tendered become free agents immediately.

Depending on how many roster spots remain after those decisions, the Yankees can then assess their capacity to add free agents or pursue trades that bring back more players than they send out. The order of operations matters: every move affects the flexibility available for the next one.

Luciano is a muscular, 6’1/215 pound, 25-year-old right-handed hitter who can play the middle infield and left-field. A longtime elite shortstop prospect in the San Francisco Giants’ organization, he signed at age 16 for $2.6 million out of the Dominican Republic in 2018. Baseball America ranked him the Giants' No. 2 prospect in 2019, then their No. 1 prospect in each of the next four years (2020–2023). He slipped back to No. 2 again in 2024, behind RHP Kyle Harrison, and in 2025, behind 1B Bryce Eldridge. Repeated unsuccessful attempts to advance him to the major leagues in 2023 and 2024, combined with his advancing age as a prospect, eventually pushed him out of the rankings. Then, over 6 weeks last winter, Luciano was sequentially waived by the Giants and claimed by the Pittsburgh Pirates, waived by the Pirates and claimed by the Baltimore Orioles, and then waived by the Orioles and claimed by the Yankees. It was almost as if the three organizations were collectively playing a game of "Marco Polo," each hoping to be the franchise to locate and unlock his considerable talent.

In 2026, Luciano rebuilt his prospect status in a big way, hitting .293/.387/.545 with 27 home runs, 78 RBI and eight stolen bases in 116 games across Double-A and Triple-A in the Yankees' system. The minor-league breakout still needs to translate against big-league pitching, as his MLB résumé, to date, remains uninspiring: just 41 games and a .217 batting average over 115 plate appearances, while still seeking his first MLB home run. He’s almost exclusively a second baseman now, although left-field and shortstop have also been part of his recent defensive past.

With Luciano already on the 40-man roster, a vacancy at second base and Amed Rosario no longer in the picture, he deserves consideration as an intriguing internal candidate not only for the second-base competition (presumably with Anthony Volpe and perhaps Luis Garcia – or possibly a middle infielder acquired by trade) but also potentially as a utility player off the bench. His defensive flexibility, athleticism, right-handed bat, elite exit velocity and power potential are appealing assets – he’s earned an opportunity to show what he can do over 200-250 major-league at bats.

The next face of the Rubik’s cube to address is the Rule 5-draft eligibles that should be protected by promotion to the 40-man roster. By my count, there are four or possibly five such minor league players that can and should be immediately promoted to the parent roster and thereby protected from the Rule 5 draft. Among these are:

RHP Carlos LeGrange – a consensus top 3 organizational prospect whose fastball sits at 98 mph (touches 102), and who has the potential to immediately make significant contributions to the MLB bullpen in 2027. Shoulder injuries slowed him down in 2026, but he still struck out nearly 30% of the Triple-A hitters he faced over 64.1 IP. Quite possibly, LeGrange is your closer of the future, perhaps as soon as 2028.

RHP Hayden Merda – another high-octane righty reliever who also features 100 mph heat and a plus slider.  Merda was good at Double-A (3.67 ERA over 41.2 IP) and bad at Triple-A (7.50 ERA over 12.0 IP), suggesting he still needs some seasoning in the minors. However, the stuff alone, suggests Merda should not be exposed to the Rule 5 Draft and added to the 40-man.

LHP Allen Facundo – The Yankees love power arms, particularly left-handers. Despite his relatively slight 6-foot, 170-pound frame, Facundo's fastball-slider combination offers the potential to develop into a high-leverage, late-inning reliever. He worked exclusively as a starter at Single-A Tampa and High-A Hudson Valley in 2026, making 22 starts, logging 114.1 innings with a 4.01 ERA. That workload represented an increase of more than 75 innings over his previous career high, a significant step forward in his development and durability. He’s worth protecting.

3B Roderick Arias – The one-time uber prospect is no longer a shortstop, but might be a possible solution at the “hot corner.” Between High-A and Double-A he put together a triple slash of .267/.349/.435 in 2026, hitting 16 HR’s and stealing 38 bags. Is that enough for Arias to claim a spot on the 40-man?

RHP Eric Reyzelman – A power arm with a potentially devastating fastball-slider combination and a legitimate shot at becoming a bullpen contributor. He struck out 75 batters in 51.2 innings in 2026 (13.1 K/9), but his season was anything but consistent. He opened the year at Double-A in impressive fashion, allowing just one earned run over his first 8.2 innings, and finished strong at Triple-A, surrendering none over his final 11.2 innings. Unfortunately, the stretch in between was dreadful: from April 29 through August 22, he gave up 33 earned runs in 31.1 innings, a 9.48 ERA. Reyzelman is exactly the kind of arm another organization might take a flyer on in the Rule 5 Draft. If the experiment fails, he’d have to pass through waivers before being offered back to the Yankees for $50,000, assuming no other club claims him. Given the bullpen defections already facing the Yankees, I could see them deciding to avoid that uncertainty and protect Reyzelman, giving him their own make-or-break opportunity in Spring Training. Or maybe not…  There is relatively little downside to leaving a borderline prospect unprotected if you believe another club might select him but be unable to keep him on the MLB roster for the entire season.

Other potential Rule 5 Draft protection candidates include LHP Kyle Carr, outfielder Jace Avina and LHP Brock Selvidge. Protecting any of them, however, would require the Yankees to create additional space on the 40-man roster. That brings us to the final deadline — and another important piece of the puzzle: Who might the Yankees reasonably non-tender on November 20?

Some have speculated that infielder Anthony Volpe, with a projected arbitration price tag of approximately $4 million, could be a non-tender candidate. Trust me, that isn't happening. Among the arbitration-eligible players, I expect infielder Luis García, catcher Austin Wells, utility man José Caballero, outfielder Heliot Ramos and LHP Ryan Weathers all to be tendered contracts and offered arbitration. Given the Yankees' needs in the bullpen, I also believe Clarke Schmidt is safe, despite a projected 2027 salary north of $4.5 million.

I see two pitchers who could reasonably be non-tendered: Fernando Cruz and former Rookie of the Year Luis Gil, both projected to earn approximately $2.3 million through arbitration.

RHP Fernando Cruz – Cruz suffered a partial UCL tear late in the season after posting a 3.13 ERA over 54.2 innings. When healthy, his splitter was incredibly effective, but at 36, he represents a significant age and injury risk. I can see the Yankees deciding to non-tender him, saving the projected $2.3 million while, perhaps more importantly, opening a valuable spot on the 40-man roster.

RHP Luis Gil – His 2024 Rookie of the Year season still suggests considerable upside, but the subsequent lat and shoulder problems have taken a toll. In 2026, he managed just 39.1 innings between the majors and minors, posting a 4.61 ERA and 7.12 FIP in his major-league work. His lack of minor-league options also creates a roster-management challenge. If the Yankees decide to protect someone like Reyzelman, Carr or Avina, something must give, and Gil could be the odd man out.

If retained, Gil would likely be viewed as bullpen depth rather than a serious rotation candidate. He currently projects as the Yankees' No. 7 or No. 8 starter at best, making it difficult to justify his roster spot given the organization's surplus of starting pitching. If another team sees value in him, a trade makes sense. Otherwise, it may simply be time for the Yankees to cut ties.

Depending on how Cashman and Company put together this Rubik's Cube, there should still be two or three roster spots available for free agents. My personal favorite to sign is LHP Adrián Morejón, although that possibility has become more complicated with the Padres extending him a qualifying offer. Morejón pitched 86 innings in 2026, posting a 2.83 ERA and an outstanding 2.37 FIP. He would fit beautifully alongside Bednar, Blackburn, Headrick and Lagrange. Combine that bullpen with the Yankees' elite starting rotation, and  a 100-win season becomes a realistic possibility.

The Yankees should also acquire a right-handed-hitting catcher through free agency. I have two candidates in mind, neither of whom received a qualifying offer, meaning they’ll be less costly from a salary standpoint and won’t cost draft capital: Tyler Stephenson (30) and Carson Kelly (32). Both should be affordable, with contracts of about $8 million to $10 million annually over two years, and both have demonstrated the ability to do considerable damage against left-handed pitching. Kelly is the far better defender, but the Yankees have done an excellent job in the past of improving the catching skills of players initially viewed as defensive liabilities, so Stephenson should not be eliminated from consideration. One thing is certain: The Yankees simply cannot continue running Austin Wells out there against left-handers after his dismal 2026 performance — 11-for-90, a .122/.192/.244 line and a .436 OPS.

Finally, the Yankees simply cannot ignore the hole at third base. Ryan McMahon's lack of offensive production is one thing; combine that with merely average defense, and it is long past time to make a change — even if that means eating the final year of his contract at $15 million. One possibility would be to try converting Luis García to third base during Spring Training, although that would be a considerable defensive gamble on the left side of the Yankee infield.

My preferred choice would be to pursue 28-year-old Teruaki Sato, the reigning Triple Crown winner and former MVP of Japan's Nippon Professional Baseball league, where he played for the Hanshin Tigers before posting. The Yankees would have an opportunity to add a potentially exceptional middle-of-the-order bat while addressing their vacancy at third base. His left-handed power would play particularly well in Yankee Stadium. Six years at $18-$20m (or two at $25m) would likely get it done.

My biggest reservation is that Sato doesn't address the Yankees' need for a right-handed bat. In fact, he would add yet another left-handed hitter to a lineup that already has several. But I wouldn't let that alone eliminate him from consideration. A player with the potential to hit 30-plus home runs deserves serious attention.

Another possibility would be to address third base through a trade, perhaps involving a player such as Anthony Volpe or Luis García. Houston's Isaac Paredes is an intriguing target. He would likely provide better defense at third base than Sato, while also delivering the right-handed power the Yankees need. Paredes is under the Astros' control for 2027 at a salary of $13.35 million, making him an appealing alternative to the cost and uncertainty of the free-agent market or an experimental position conversion by Garcia/Volpe.

If the Yankees want to get creative, perhaps a conversation with the St. Louis Cardinals would be worthwhile. The Cardinals have a surplus of talented catchers, including one I'd target: All Star Iván Herrera, a defensively challenged but offensively gifted right-handed hitter. They also have a third baseman, Nolan Gorman, whose future with the organization is uncertain and who could be a non-tender candidate. Meanwhile, the Cardinals desperately need more consistent starting pitching — and the Yankees have plenty to spare.

How about offering Will Warren and Luis Gil in exchange for Herrera, while simultaneously taking a flyer on Gorman? It might be a creative way to address two significant roster needs — a right-handed-hitting catcher and a potential third base upgrade over McMahon — in one transaction. Warren would give St. Louis a controllable, proven starting pitcher with considerable upside, while Gil offers another arm with a Rookie of the Year pedigree and the potential to regain his earlier form. Gorman would be a reclamation project, but his power is intriguing (especially with the short porch in right), and Herrera could become an important offensive contributor behind the plate or at DH, with some additional versatility from his experience at first base and in left field. It's certainly a conversation worth having.  Notably Gorman would be controllable until 2029 and Herrera until 2030.

The Yankees have no shortage of pieces to work with this off-season, and in some respects, they are starting from a position of strength. An elite starting rotation, several promising young players already on the 40-man roster, a handful of intriguing prospects ready for opportunities, and sufficient financial resources should give Cashman the flexibility to address most of the team's shortcomings. But solving this Rubik’s Cube will require more than simply making a series of moves. Each decision must complement the next, and every acquisition must be considered in the context of the roster as a whole. A solution at third base that creates another problem at first base or DH, or a bullpen signing that leaves no room for a needed catcher, isn't really a solution at all.

The clock is ticking, and the margin for error is shrinking. Cashman has three weeks to put the initial pieces in place before the expected lockout brings baseball operations to a halt. The Yankees don't need another offseason of half-measures, short-term fixes and unfinished business. They need a coherent plan, some creativity in the trade market and the willingness to make difficult decisions about players who no longer fit. The objective is clear: build a roster capable of winning 100 games and, more importantly, competing for a World Series championship in 2027. The pieces are there. Now it's up to Cashman to put them together.