Yankees 2026 Offseason Guide on Free Agents, Trade Targets, More Roster Shakeups After ALDS Loss

Well, it's official: The New York Yankees are mired in their longest World Series drought in more than a century.

With Wednesday's loss to the Tampa Bay Rays, we are now guaranteed a 17th consecutive world champion that isn't the Bronx Bombers, breaking the previous past-century record of 16 in a row from 1979-1995. (Excluding 1994, when there was no World Series.)

As has been the case on an annual basis in recent years, the immediate question is whether the Yankees will stick with Aaron Boone as manager or shake things up. He has one year left on the extension they gave him two Februaries ago, but the seat is hotter than ever.

Once that part is settled, though, it'll be on to the roster moves meant to end this embarrassing drought.

Ahead, we'll take a look at New York's most noteworthy free agents and its best options for replacing them—whether internally, via free agency or via trade—before offering up a super early look at what the Yankees' 26-man roster might look like on Opening Day.

Many Yankees fans turned a cold shoulder to Chisholm as he fell well short of his preseason promise of a 50/50 season . (That fielding blunder in Game 2 against Tampa Bay didn't help matters.)

However, they'll likely extend him the estimated one-year, $23.1M qualifying offer. After all, he reached 19 home runs and 41 stolen bases, bringing his "since the beginning of 2021" totals to 125 and 169, respectively. Those numbers match Bobby Witt Jr. (123 and 193) and Trea Turner (130 and 165), even though Chisholm has received 539 fewer plate appearances than the former and 1,108 fewer than the latter.

He'll likely reject the offer, though, and seek something closer to the nine-figure payday most analysts anticipated heading into this season. And with George Lombard Jr., Anthony Volpe and José Caballero all available for middle infield duties for the foreseeable future, New York likely won't be the one giving him that mega deal.

Beyond Chisholm, both Grisham and Goldschmidt are considerable losses, each playing in more than 100 games this season.

They aren't exactly deal-breaker losses, though. Spencer Jones is arguably already better than Grisham and should be the everyday center fielder in 2027. And though they'll miss Goldy's bat against left-handed pitching, having a right-handed platoon bat for Ben Rice is no longer the necessity it seemed to be one year ago.

All six of these pitchers are relievers.

That is wonderful news for New York's fully intact, arguably too-crowded starting rotation, but problematic for the bullpen, to say the least.

Bednar is the biggest one by far, owner of 35 saves and a 2.47 ERA this season. Like Chisholm, he could also be headed for a qualifying offer of an estimated $23.1M, but is expected to decline it in pursuit of something closer to a four-year, $66M contract.

If he does walk, there's no obvious in-house option to take his place. The only returning Yankee who recorded any saves for them in 2026 is Fernando Cruz—and he's trying to rehab a partially torn UCL without surgery.

Also, if they do let Bednar walk, it would be the first time they've needed to replace a pitcher with at least 35 saves since Andrew Miller took David Robertson's place during the 2014-15 offseason.

Notably, Blackburn was worth even more wins above replacement than Bednar, per Baseball-Reference . In fact, B-R graded Blackburn as the third-most valuable reliever in all of baseball, tied with Mason Miller and trailing only Jhoan Duran and Louis Varland. (That sure did come out of nowhere, though, as Blackburn entered 2026 with a 5.22 ERA over the previous eight seasons.)

As we just discussed, not only is David Bednar headed for free agency, but so are Paul Blackburn, Tim Hill and Ryan Yarbrough.

That's four of the five Yankees pitchers who logged at least 55 relief innings in 2026, leaving Brent Headrick as one of the few established bullpen guys still under contract.

Not only is this New York's biggest need, but it might also be just about their entire offseason focus.

Austin Wells at least turned things around at the dish for a respectable finish after entering the All-Star Break with a horrendous .504 OPS. And behind the plate, he won the third-most ABS challenges among catchers in 2026.

Still, Yankees catchers had some of the worst offensive numbers in the majors, batting .196 as a group. It's still hard to believe they did nothing to address that ahead of the trade deadline, since it was even worse then.

Even with Jazz Chisholm Jr. likely out of the picture, this is more of a "luxury want" than a "desperate need."

If the Yankees simply do nothing and go into 2027 with Ryan McMahon at third base, George Lombard Jr. at shortstop, Anthony Volpe at second base, Ben Rice at first base, José Caballero as the 3B/SS backup and Luis García Jr. as the 1B/2B backup, it certainly wouldn't be the worst infield situation on Opening Day.

But the Yankees can make "luxury want" signings, and guys like Brandon Lowe and Luis Arraez are there for the taking.

Predicting the Outcome for Each Team's Top Free Agent 🔮

Now that George Lombard Jr. is no longer a prospect, New York's top player in the farm system is probably shortstop Dax Kilby . Don't expect to see him any time soon, though. The now 19-year-old was their first-round draft pick in 2025, but he missed most of this season with a hamstring injury. He hasn't even progressed to High-A Hudson Valley, let alone Double-A or Triple-A.

The two most likely to factor into the mix in 2027 are right-handed pitchers Elmer Rodríguez and Carlos Lagrange .

The former made six big-league starts this season, including a quality start against Houston in late August. (He was also scheduled to start the season finale before it got rained out.) However, he kept getting sent back down to Triple-A once the high-priced starter he was filling in for was able to return from injury, and could be in a similar "break in case of emergency" role next year.

The latter was a starter for the first couple of months at Triple-A before transitioning into a relief role. Had he not missed about 10 weeks with a shoulder injury, he likely would have been in the big-league bullpen in 2026. Got to like his chances of making the cut for next year's 'pen, given all that they're losing from that position group.

Pete Fairbanks is also available. Maybe Kenley Jansen and Carlos Estévez, too, if their club options are declined. But Bednar and Iglesias are the clear top options for any team looking to sign an established closer.

The deciding factor between the two options is how committed the Yankees are willing to be.

Bednar is heading into his age-32 season and should be able to command at least a three-year deal, if not four years. Iglesias, on the other hand, turns 37 in January and might be gettable on a one-year deal. (Either one is likely to sign for an AAV in the $15M-$17M range.)

Closers get all of the bullpen love, but very few relief pitchers have been more consistently dominant over the past three seasons than San Diego's Morejón. He relies heavily on his sinker, but his four-pitch arsenal was solid, leading to more than 100 strikeouts in 2026 alone.

Maybe they even sign him as the closer after he set up admirably for Robert Suarez and Mason Miller for years? He'd also be a great target for eighth-inning duties in Paul Blackburn's stead.

Everyone expected the Yankees to trade for Jeffers, right up until the Twins got hot in late July and decided to be buyers instead of sellers.

Jeffers has had a .782 OPS over the past four seasons, one of the 10 or so most valuable catchers in the sport during that time. Whether he supplants Austin Wells as the primary catcher or it's more of a 50/50 split, he could be a major addition to New York's lineup.

Good luck finding a second baseman who can match both Jazz Chisholm Jr.'s power and speed, but Brandon Lowe would certainly handle the first with 66 home runs and an .806 OPS over the past two seasons. And Yankee Stadium's short porch in right would be conducive to his left-handed power.

Before we get into the actual players New York could target, let's note that the Yankees are in a tremendous position to wheel and deal.

As is, the big four in the starting rotation are Cam Schlittler, Max Fried, Gerrit Cole and Carlos Rodón, each of whom is signed through at least 2028. And for the No. 5 spot in that rotation, it's an absurd logjam of Will Warren, Ryan Weathers, Luis Gil, Clarke Schmidt and Elmer Rodriguez—with Schmidt the only member of that bunch who isn't under team control for at least two more seasons.

It's an embarrassment of riches. And while they could mimic the Dodgers by hoarding those arms like a dragon guarding a treasure pile, they'll probably try to trade at least one of those candidates for the No. 5 spot to upgrade elsewhere.

Remember late July? When the Padres were 50-53, 11th in the NL standings and everyone started speculating about a second straight summer with a Mason Miller blockbuster?

That never happened, obviously, but could Miller (with three years of arbitration eligibility remaining) be the belle of this winter's trade block ball?

We'll say this much for the Padres: They desperately need to address their 2027 starting rotation. Robbie Ray, Casey Mize and Walker Buehler are unrestricted free agents. Michael King can opt out of the two years left on his contract and is all but guaranteed to do so.

If he does, the Padres are looking at a mess, hoping Yu Darvish returns at 40 after missing all of 2026 and that Joe Musgrove can amount to something after missing both 2025 and 2026.

Trading Miller for a package of Luis Gil and Will Warren could be their saving grace.

Between Freddy Peralta this past winter, Devin Williams the previous year and Corbin Burnes the offseason before that, we have plenty of evidence that the Brewers are not afraid to trade away a star player ahead of his final season of team control.

Nor should they be afraid, as they inexplicably just keep getting better every time they do it.

Well, William Contreras has a $14.5M club option for 2027. The Brewers could definitely benefit from another starting pitcher or two in a rotation that can get questionable quickly beyond Jacob Misiorowski and Logan Henderson.

While Milwaukee might be actively shopping Contreras, De La Cruz is far more of an "at least make them say no" trade candidate.

But with the never-ending reports of De La Cruz refusing to even engage in long-term extension talks with the Reds, the Yankees should make them say no.

They would at least need to offer up George Lombard Jr., probably Spencer Jones and at least one of the aforementioned "maybe the No. 5 option in 2027" starting pitchers to even raise an eyebrow from Cincinnati's front office. But if they could pull it off, it would give the Yankees at least three years' worth of a superstar at shortstop instead of their current plan of a revolving door in the middle infield.

Starting Lineup (vs. Blue Jays RHP Dylan Cease)

1B Ben Rice RF Aaron Judge LF Cody Bellinger DH Giancarlo Stanton 2B Luis García Jr. C William Contreras CF Spencer Jones 3B Ryan McMahon SS George Lombard Jr.

C Austin Wells IF Anthony Volpe UTIL José Caballero OF Heliot Ramos or Jasson Dominguez

RHP Cam Schlittler LHP Max Fried RHP Gerrit Cole LHP Carlos Rodón RHP Will Warren

RHP David Bednar LHP Adrián Morejón LHP Brent Headrick RHP Kevin Ginkel RHP Yerry De Los Santos RHP Carlos Lagrange RHP Clarke Schmidt RHP Fernando Cruz

Even with Jazz Chisholm Jr., Trent Grisham and Paul Goldschmidt all expected to walk, the only significant changes we're projecting among the position players are a healthy Giancarlo Stanton at DH, Luis García Jr. shifting from first base back to second base and a trade for William Contreras. If they can't pry him away from Milwaukee, signing Ryan Jeffers is also very much on the table.

For the rotation, Will Warren is the guess for the No. 5 spot, as he has logged more innings over the past two seasons than any other Yankee. Clarke Schmidt sticks around in a bulk relief role in his final season before hitting free agency, while Ryan Weathers and Luis Gil are strong candidates to be traded this winter.

In the bullpen, re-signing David Bednar is the top priority, followed shortly by landing the best reliever available this winter in LHP Adrián Morejón. They still have other work to do, especially if Fernando Cruz can't rehab that partially torn UCL. Kevin Ginkel is a total dart throw, but he is one of many free agents who could enter New York's sixth/seventh inning mix in 2027.