The New York Yankees Have a Clear Path to an Even Better 2027 Roster

With one of baseball's largest payrolls, a roster filled with high-priced stars and an unrivaled franchise reputation, the New York Yankees are in a perennial state of World Series-or-bust.

Simply making the playoffs, or even reaching the Fall Classic, does not constitute a successful season for an organization that has been searching for title No. 28 since they last hoisted the trophy in 2009.

With an 87-63 record, they have already clinched a playoff spot, but they are 3.5 games back in the AL East and on a collision course with the Boston Red Sox in the AL Wild Card Series once again.

Can this team win it all?

Absolutely, simply getting to October is half the battle; then it's just a matter of getting hot at the right time. This is not the best team in baseball. The odds will be stacked against them when the MLB postseason gets underway.

So what's next if they come up short again?

Trent Grisham ($22.025 million) and Jazz Chisholm ($10.2 million) coming off the books give the club some financial flexibility. There's a case to be made that they don't need to reinvest any of that money on the offensive side of things.

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They made their splashy addition when they acquired Luis García Jr. and his additional year of club control at the trade deadline, which paves the way for their Opening Day lineup to potentially look something like this:

DH Ben Rice
LF Cody Bellinger
RF Aaron Judge
1B Luis García Jr.
CF Spencer Jones
3B Ryan McMahon
SS George Lombard Jr.
2B Anthony Volpe
C Austin Wells

At this point, it's reasonable to treat anything you get from Giancarlo Stanton as a bonus, rather than relying on him to fill a spot. Versatile José Caballero returns in the super-utility role, while Heliot Ramos serves as the fourth outfielder and a platoon option against left-handed pitching.

They could explore an upgrade at catcher like Ryan Jeffers, or kick the tires on a reunion with Gleyber Torres or another second baseman on the market. With a full season of García and a healthy Aaron Judge, that group has the potential to be a top-tier offense, even with some holes at the bottom.

Then there's the starting rotation, which could be the best in baseball in 2027 if everyone is healthy.

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

That's without even mentioning a healthy Luis Gil or rising prospect Elmer Rodríguez, so there's no reason for the Yankees to be part of the Tarik Skubal sweepstakes or pursue any of the market's other top starting pitching options.

That leaves the bullpen, and outside of one breakout lefty, the Yankees will essentially be rebuilding from the ground up this winter. This is their chance to transform their roster into an October juggernaut.

Here's a look at every reliever who has made at least 30 appearances for the Yankees this season, along with their status for 2027:

RHP David Bednar — Free Agent
RHP Jake Bird — Traded (WAS)
RHP Paul Blackburn — Free Agent
RHP Fernando Cruz — Injured, potential Tommy John
RHP Camilo Doval — Traded (PIT)
LHP Brent Headrick — Controllable through 2031
LHP Tim Hill — Free Agent
LHP Ryan Yarborough — Free Agent

With a 1.94 ERA, 1.18 WHIP and 11.1 K/9 while logging 29 holds in 76 appearances, Brent Headrick has been one of the best relievers in baseball, but one standout setup reliever is not a bullpen. It's a good starting point, but this is a complete rebuild.

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Already operating above the luxury tax threshold, the front office could simply tuck the savings from departing free agents into its pocket, lower its tax hit and cobble together a relief corps of low-cost veterans.

Or, they could build the best bullpen in baseball:

RHP Luis Gil
RHP Carlos Lagrange (R)
LHP Brock Burke (2 years, $10 million)
RHP Jason Adam (1 year, $7 million)
LHP Brent Headrick
RHP Bryan Abreu (3 years, $30 million)
LHP Adrián Morejón (4 years, $60 million)
RHP David Bednar (3 years, $45 million)

With a 2.66 ERA, 10.1 K/9 and 34 saves in 37 chances, David Bednar has been one of the most reliable closers in baseball. Bringing him back should be a top priority. There are many talented bullpen arms on the market this winter, but few have his ninth-inning track record. The ones who do are on the other side of their prime, like Raisel Iglesias and Kenley Jansen.

Once the closer's role is solidified, Adrián Morejón and Bryan Abreu would provide a pair of high-octane setup arms with swing-and-miss stuff and multiple prime seasons left in the tank.

Morejón, 27, has a 2.87 ERA and 100 strikeouts in 81.2 innings this season, pitching off a fastball that averages 99.5 mph and a changeup that has generated a 54.1 percent whiff rate.

The Yankees actually made a push to acquire him at the deadline, with a package that reportedly included controllable starter Will Warren. He could come with a qualifying offer attached and a hefty AAV ask, but he's one of the best in the business.

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Abreu, 29, is a bit more of a wild card, but one with massive upside.

After a terrific four-year stretch where he logged a 2.30 ERA and 12.7 K/9 across 275 appearances out of the Houston bullpen, he has pitched to a 3.86 ERA this season, partly due to a spike in his walk rate from 10.5 to 15.9 percent. However, his fastball-slider pairing remains elite. This down year might actually make signing both high-leverage relievers a more realistic goal.

Jason Adam (36 G, 2.51 ERA) and Brock Burke (73 G, 2.43 ERA) should come at a more reasonable cost. Adam because he missed time due to injury in 2026. Burke because he profiles more as a middle relief workhorse than a late-inning fireman on a contender. Both are quality additions that will be near the top of more than a few teams' shopping lists.

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That leaves two open spots, one of which can be filled by Luis Gil, Ryan Weathers or whoever misses out on a rotation spot. The other spot gives hard-throwing top prospect Carlos Lagrange a clear path to make his case this spring.

Those projected contract figures add $52 million to the 2027 payroll. Not an insignificant number by any means, but it could be a small price to pay if it's what pushes this club over the top in October.

First things first, the Yankees have a 2026 playoff push to focus on. If they fall short of the ultimate goal once again, focusing their offseason efforts on building an untouchable relief corps could be the missing piece.