New York Yankees: The Aftermath Part Two (Players)

“New York Yankees: The Aftermath” is a three-part series with my suggestions on how the Yankees should proceed with their leadership (part one), players (part two), and roster construction (part three).

DEVELOPING A PLAN FOR 2027
In Part One, I stated the unpopular opinion that Hal Steinbrenner, Brian Cashman, and Aaron Boone are doing a good job and deserve the opportunity to continue to lead the efforts toward title #28.

Now, that doesn’t mean I’m looking for another year of running it back. The Yanks need to make tweaks to their lineup to increase their positional flexibility, improve their defense, and acquire more “bat-on-ball” hitters (formerly known as contact hitters).

The next time they face a fundamentally sound team in the playoffs like the 2025 Toronto Blue Jays or 2026 Tampa Bay Rays, they need to be ready.

We are going to analyze what the Yankees should do with their 10 free agents, who they should send to winter ball, and who should be shopped around as trade bait. Plus, we finish Part Two with an updated lineup based on our suggestions.

YANKEES’ TEN FREE AGENTS

Retain

1. David Bednar has checked all the boxes since being acquired from the Pittsburgh Pirates on July 31, 2025. He’s proven he can handle the bright lights in the postseason, and has shown the ability to bounce back from poor outings. Plus, the 32-year-old has emerged as a leader in the bullpen. Sign Bednar to a 4-year/$52m contract to retain your closer.

2. Paul Blackburn transformed himself from a journeyman starter to an elite setup man. Due to his track record, I would want to see the 32-year-old right-hander back up that season before committing long-term. Sign Blackburn to a 1-year/$8m contract to keep the Brent Headrick/Blackburn lefty-righty setup duo intact.
   
   
3. Ryan Yarbrough served as the Yankees long reliever this past season. In 38 games, including 2 starts, he pitched 63.1 innings with a 3.69 ERA. Considering the 34-year-old is left-handed, and there is a chance that the Yankees may elect to trade some of their rotation depth to fill other needs, I would offer Yarbrough a small raise to stay. Sign Yarbrough to a 1-year/$3m contract.

Say Goodbye

4. Trent Grisham was the “other guy” acquired in the Juan Soto trade with San Diego. After failing to get into a playoff game during the Yanks’ run to the World Series in 2024, he cashed in on a career year in 2025 after hitting 34 HRs before signing the qualifying offer for over $22m. Unfortunately, he regressed to his norm this season at the plate, and took a step back in the field. Let Grisham walk.
   
   
5. Jazz Chisholm is so talented that we didn’t completely discount him when he said this past spring that his goal was to join Shohei Ohtani in the 50/50 club. There’s a chance he’s going to find a comfortable, forgiven market and put up those types of spectacular numbers. But it can’t be in the While I find his play at 2B no more frustrating than that of his predecessors Chuck Knoblauch, Alfonso Soriano, Robinson Cano, and Gleyber Torres — Jazz’s ‘postgame, take no responsibility, would do it again’ comments just hit different. Let Chisholm walk.
   
   
6. Paul Goldschmidt is going to the Hall of Fame. He came back to the Yankees at age 39 with low expectations and became a very reliable, important player. Saying goodbye to your most consistent defensive infielder seems counterintuitive, but the Yanks will need his roster spot. Let Goldschmidt walk, but offer him a job in the organization.
   
   
7. Amed Rosario was a player that I wanted on the Yankees for many years. In his year-plus tenure, he had some timely hits and was considered a good teammate. However, he doesn’t fit the current roster construction as they need utility players who can defend. Let Rosario walk.
   
   
8. Tim Hill was remarkably consistent through most of his 2+ year tenure, but the 36-year-old left-hander was a liability down the stretch, pitching to a 9.53 ERA in September. Let Hill walk.
   
   
9. John Schreiber was claimed off waivers on August 31 and pitched well enough to make the postseason roster. However, at 32 years old, he does not fit the profile of what the Yankees need in middle relief (young with minor league options). Let Schreiber walk.
   
   
10. Michael Fulmer was released by the Los Angeles Angels on August 25, 2026, and signed by the Yanks the next day. The 33-year-old is not part of the future. Let Fulmer walk.
    

WINTER BALL
Yankees management should ask Jasson Dominguez, Luis Garcia Jr, Spencer Jones, and Anthony Volpe to play a few weeks of winter ball for defensive purposes.

1. Jasson Dominguez is no longer an untouchable, but his trade value is quite low. Winter ball would be a good opportunity for him to play all three outfield positions to showcase himself to the Yankees and the rest of the league.
   
   
2. Luis Garcia Jr is a seven-year MLB veteran who has played 508 games at 2B, 133 games at 1B, and 70 games at SS in his career. Can he play 3B? It would be beneficial for the Yanks to find out in the fall rather than waiting for the spring.
   
   
3. Unless the Yankees acquire a CF, Spencer Jones will enter Spring Training as the favorite to earn that job on a full-time basis. Winter ball will enable him to play center field every day for a few weeks to work on the mistakes he made down the stretch.
   
   
4. Anthony Volpe looked comfortable at 2B, but a few more weeks of honing his skills, including his new approach at the plate, makes sense.

TRADE BAIT

• Jasson Dominguez took a step back in 2026. I’m still confident he will find his footing in the batter’s box and running the bases, but he hasn’t given us any reason to believe he’s going to become league average in the OF. The Yanks should not give him away, but we believe they will be willing to deal him. Listen to offers.
  
  
• Luis Garcia Jr was acquired at the trade deadline from the Washington Nationals. His positional flexibility (see above) and raw left-handed power make him a strong candidate to survive the winter. However, he is a poor positional fit. If the Yanks can acquire a smoother fielding 1B/3B with a lifetime OBP better than Garcia’s .301, they should jump at the move. Listen to offers.
  
  
• Ryan McMahon legitimately batted .254 with 23 HRs, 86 RBIs, and a .779 OPS in 2021 for the Colorado Rockies. As late as 2024 he made the NL All-Star team. However, by the end of this season he was not only a below-average hitter, but he lost his confidence in the field. The Yankees should find him a new home.
  
  
• Luis Gil and Clarke Schmidt are expected to enter spring training healthy and compete for bullpen spots due to the depth of the Yankees starting rotation. However, the two right-handed pitchers may provide more value as trade bait as the Yankees try to fill other holes. Yankees should not be in a hurry to deal their starting depth, but with nine of their Top 10 prospects being pitchers, they should listen to offers for Gil and Schmidt.

AWKWARD CONVERSATION #1
The last four times Aaron Judge went on the shelf; he was injured playing defense.

2023 — Injured his right big toe crashing into Dodger Stadium’s bullpen gate (6-3).
2025 — Right elbow flexor strain throwing home from RF against Toronto (7-22).
2026 — Right first-rib stress fracture diving against Houston (4-26).
2026 — Right calf strain while playing defense in Minnesota (9-16).

Aaron Judge is an above-average athlete and defensive outfielder. At 34, he is not going to want to become a full-time DH, but strong action is needed to put Judge in the best position to help the team in October.

Now, if I were running the organization, Boone wouldn’t have to handle this on his own. It’s too inflammable considering the effect it will have on Ben Rice and Giancarlo Stanton. Instead, the entire chain of command should sit with the captain to map out the best way to keep his bat in the lineup.


AWKWARD CONVERSATION #2
Giancarlo Stanton has played 1750 career games, compiling 456 HRs, 1183 RBIs, and a career .872 OPS. He’s a five-time All-Star, former NL MVP, and will be in the conversation to make the Hall of Fame once he retires.

But right now, whether it’s to make room for Aaron Judge, Ben Rice, or a combination of both, it’s time for Stanton to hang up his pinstripes after nine injury-plagued seasons. Contractually, he has a minimum of $35m remaining on his deal, in the form of a $25m guaranteed salary in 2027 and a $10m buyout in 2028.

However, since the Miami Marlins are obligated to contribute $10m in both 2027/2028, the Yanks’ net remaining obligation would be only $15m after the Miami’s contributions. Stanton has respect in the Yankees locker room, but retaining him as an expensive part-time DH and pinch-hitter would make no sense.  Whether it’s a buyout or trade, the time has come.


WINTER MEETINGS PROJECTED ROSTER
Prior to the Yankees acquiring any players via free agency, trade, or waivers, here’s how their projected 26-man roster looks based on the moves proposed above. We will work on final roster construction in “New York Yankees: The Aftermath Part Three (Roster Construction)”

ICYMI “New York Yankees: The Aftermath Part One (Leadership)”