World Series Loss Leaves Big Questions for the Yankees

The “Goliath versus Goliath” World Series has come to the end. And for the New York Yankees the quest for title number 28 will have to wait another year.

And it wasn’t the most glamourous of showings for the Bronx Bombers. Other than an 11-4 Game 4 victory, and some early inning power in their Game 5 loss, they looked outmatched against the juggernaut that is the Los Angeles Dodgers.

While it may be painful now, it’s not all doom and gloom in the Bronx though as the Yankees still have a lot to hold their heads high about in regard to the 2024 season.

They took home their first AL Pennant in 15 seasons after a AL East division winning, 94-win campaign.

In doing so they sported the presumptive AL MVP in Aaron Judge, a presumptive AL MVP finalist in Juan Soto, a couple of bright young rookies in Austin Wells and Luis Gil and they may very well have found one of the league’s best closers for years to come in Luke Weaver.

But now that the season has come to the end, there’s no time for the Yankees to revel in their successes of 2024, and there’s equally no time to dwell on how they came up just short.

The Yankees face some major questions this offseason. And now that they’ve shown they have what it takes to make it to the World Series, the stakes to get things right this winter and find the right answers before Opening Day are higher than they’ve been in the greater part of two decades.

And their needs span across the board, so if they hope to the right the wrongs of this year’s Fall Classic come 2025, there’s no time to waste.

So what are the biggest questions facing the Yankees this winter?

Will Juan Soto Don Yankee Pinstripes in 2025?

While this isn’t nearly the only question New York faces this offseason, it is definitely the one that the entire MLB will be watching.

The Yankees offense was undoubtedly better in 2024 after missing the postseason entirely in 2023, and it was Soto, alongside Judge, who led them to such feats.

Soto will have no shortage of suitors lining up for a chance at obtaining his signature this offseason. So it now becomes a matter of whether or not the Yankees have sold Soto and his agent Scott Boras of the project in New York, and whether or not they can put up the right amount of money to convince him to stay.

And if we’ve learned anything about Boras clients in past offseason, this likely won’t be a question that will be answered in a quick manner.

As important as Soto has been to the Yankees this season, the foundation they already have in place in the outfield makes this issue a little less of a daunting task compared to the other matters facing them this winter.

Internally, New York already has their undeniable anchor in the outfield in Judge coming off arguably the best season of his career, along with Just Baseball’s seventh-ranked prospect in Jasson Dominguez, who’s likely set for his first full big-league season in 2025.

And there are several other big-name corner outfield options on the free agent market including Anthony Santander, Teoscar Hernández and Jurickson Profar, should they find the need to look elsewhere to round out their starting outfield.

Who Will Man First Base in 2025?

It’s safe to say the Anthony Rizzo experiment in New York has produced mixed results in his three-and-a-half year stint as a Yankee.

After acquiring him at the 2021 trade deadline, it’s been a tale two Rizzos, with the first half of his stint looking far more promising than the second half, which has been largely marred by injury.

Despite his unimpressive 2024 season, Rizzo has tried his best to redeem himself this year with a strong postseason performance, but with the Yankees holding a club option on him in 2025, it seems likely they won’t be bringing him back for $17 million.

While deciding whether or not to exercise option is technically the first question they need to address at first base, the real question is; who will the Yankees turn to to man first in 2025 and beyond?

While younger guys like Oswaldo Cabrera and Ben Rice have made appearances at the position this season, they don’t nearly offer the long-term answer that this question warrants.

If the Yankees hope to make another pennant run next season, it seems they’ll have to hit the open market for a solution.

And with how high the Yankees payroll has been for decades, big free-agent names at the position like Pete Alonso and Christian Walker will likely be in play.

Who Will Be Anthony Volpe’s Middle Infield Partner?

Despite a slower start to his career than his once prized prospect status projected, Anthony Volpe seems to the have the left side of the Yankees’ middle infield covered for the next few seasons.

But what about the right side?

At this point it seems all but likely that Gleyber Torres will test the open market this winter, as it would be surprising to see New York extend a qualifying offer to him after the inconsistent string of seasons with the club.

Torres however, is the best second baseman on the free agent market in a weak positional class, indicating an internal fix is probably in the cards in the Bronx.

The easiest answer would be to move Jazz Chisholm Jr. back to second base, which was their original plan for him when they acquired him at the trade deadline before Torres refused to switch to third base.

But if Chisholm moves back to second, then who now occupies third?

The Yankees could turn to the duo of Oswaldo Cabrera and Jon Berti to fill innings, or they could tap into the well known as Steinbrenner fortune, to hit the open market and target a name like Alex Bregman.

Regardless of how the Yankees approach this situation, the moral of the story is that, despite his inconsistencies in his time in New York, the departure of Torres raises more questions than you might initially think.

What Do You Do with DJ LeMahieu?

Since his 2019 and 2020 seasons that saw him finish fourth and third, respectively, in AL MVP voting, DJ LeMahieu‘s production has rapidly declined in recent years.

After a season where he struggled to stay on the field, and when he was on the field sported a putrid 52 wRC+ and career-low .527 OPS, with just two years left on his contract the Yankees will need to evaluate what to do with LeMahieu this offseason.

LeMahieu was known for his ability to move around the infield, covering first, second and third, but he hasn’t appeared at second base since 2023, so his utility value has lost some luster.

And even though the corner infield spots either are or could be questions for New York this offseason, LeMahieu’s poor play has him trending more towards being cut rather than being an answer to the Yankees’ problems.

New York figures to be very active on the open market this offseason, and with LeMahieu slated to make $15 million per year for the next two seasons, they need to ask themselves is it worth it to cut him and eat his salary so there’s suddenly space on the roster and in the payroll to get bold?

Because the production they got from him in 2024 is not something that serves to propel them to a World Series title in 2025.

How Will New York Keep Up the Backend of the Bullpen?

The Yankees elevated their relief pitching game as a whole in 2024, especially in the second half of the regular season and postseason. This was in large part thanks to their “big four” in Tommy Kahnle, Clay Holmes, Jake Cousins and newly minted closer Luke Weaver.

It’s a shoe-in that Weaver will have his $2.5 million club option exercised in 2025, and Cousins has one more pre-arbitration year under his belt.

But both Holmes and Kahnle will enter free agency this offseason, which leaves the Yankees to figure out how they are to keep up appearances and ensure their bullpen is as strong next season as it was this season.

There’s always a real possibility both arms are back next year.

After a three-and-a-half year stint in the Bronx from 2017 to 2020, Kahnle found himself making his way back to the Yankees in 2023 after a very brief one-year stop with the Dodgers the season prior. So with the familiarity already there for both parties, it wouldn’t be a shock to see him come back.

It’ll be a matter of whether the Yankees think he can repeat his solid 2024 season in 2025 with the limited pitch mix he utilizes.

Holmes is interesting case, as after losing his closing role late in the regular season to Weaver, due to an egregious 13 blown saves in 2024, his free agent value has inevitably decreased than where it was at on opening day.

But given his recent All-Star recognition as a closer, despite the poor performance in 2024, Holmes could very well opt to find a place where he regains his closer’s role because Weaver has the Yankee job all but locked up after a wildly impressive postseason.

And with a deeper free agent class at the relief position available to explore, the Yankees certainly have the opportunity to strengthen externally if they wish to look beyond Kahnle and Holmes.

But if this postseason taught us anything, it’s the value that a good bullpen provides to a contending team, meaning the Yankees have to do something to avoid regression in the ‘pen.

The Yankees Have Their Work Cut Out for Them

As I touched on earlier, the Yankees have a lot to be excited about moving forward after a pennant run.

But at the end of the day, this team fell short, there’s no denying that. And like every team that falls short, questions will be asked of what can be done to improve this team so that they don’t find themselves in the same situation a year from now.

It’s indisputable that New York has a great core to build their offseason plans off of this winter. Their lineup is lead by arguably the best hitter in baseball in Aaron Judge, with talented names like Jazz Chisholm Jr., Giancarlo Stanton supporting him.

They have a starting rotation led by one of MLB’s top arms Gerrit Cole. And a Luke Weaver-anchored ‘pen already gives them a leg up on many other teams’ relief corps.

But that doesn’t excuse them from the work that needs to be done and the matters that need to be addressed. Their entire right half of the diamond is in question (1B, 2B, RF), they’re at risk of losing half of their most talented relievers and there are veteran names on this team that aren’t the veteran presences they once were occupying valuable spots on the active roster.

So while it may sting now, there’s no time for Brian Cashman and the Yankees’ front office to lick their wounds if they want the best chance of avoiding this again in 2025 and finally bringing the Commissioner’s Trophy back to the Bronx.