Major League Baseball

Yankees offseason primer: 5 burning questions, including how will they upgrade their roster?

Updated Nov. 27, 2023 3:06 p.m. ET

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Jake Mintz

FOX Sports MLB Analyst

Things are ... weird in the Bronx.

The 2023 Yankees were a cornucopia of mediocrity, a hyped, expensive tidal wave of underwhelming disappointment. Aaron Judge and Gerrit Cole were predictably fantastic, but the supporting cast was a sandpaper mattress, a tissue-paper seat belt, a hornet casserole. 

High-paid supposed-to-be-good superstars like Carlos Rodón, Giancarlo Stanton and DJ LeMahieu were disastrous to meh. Few of the young players developed into valuable contributors. There were flashes, sure, reasons for optimism, yeah, but promise doesn't win championships.

And for the first time since the Obama Administration, the Yankees missed the playoffs while posting the smallest win total in a full season since 1992. The organization, just a year removed from 99 wins and a trip to the ALCS, appeared discombobulated. There were rumors of an outside firm being hired to investigate the mess, and while that never actually occurred, the buzz tells the story.

Then, during the GM Meetings in early November, longtime senior vice president Brian Cashman unleashed a legendary rant, defending his front office and its perceived reliance on analytics from outside criticism. That bizarre tirade, while entertaining, only furthered suspicions that the organization is somewhat out of sorts.

Messaging aside, the Yanks still have a roster to upgrade this winter, a roster that won just 82 ballgames. Per usual, New York and its massive budget will be associated with many of the top free agents, but this year's class doesn't exactly match up well with the Yankees' holes and needs.

Let's dig in.

1. How do they upgrade the outfield?

By bWAR, the Yankees had the single least valuable outfield in baseball last season. Injuries limited Judge to only 288 plate appearances as an outfielder, which pushed offensive pumpkins like Harrison Bader, Isiah Kiner-Falefa and Oswaldo Cabrera into significant action. Scrap-heap discoveries like Willie Calhoun, Jake Bauers and Billy McKinney played admirably but insufficiently. Jasson Domínguez tantalized before tearing his UCL, which will keep him sidelined for most of 2024.

And while the Yankees are sure to add to their outfield mix this winter, their current starting lineup includes Judge, the un-trusted Estevan Florial and the unproven Everson Pereira (Giancarlo Stanton should still see the majority of his time at DH). They need at least one outside addition in the grass, probably two.

The only slam-dunk center fielder on the market this winter is Cody Bellinger, who despite an encouraging bounce-back campaign with the Cubs comes with an avalanche of question marks. His left-handed stick would play great with Yankee Stadium's short porch in right field, but Bellinger was bad enough this time last year to warrant a non-tender from the Dodgers. Is he really the long-term solution in center field? Kevin Kiermaier and Michael A. Taylor are solid fallback options, good veteran defenders coming off career offensive campaigns (don't expect a Bader or Aaron Hicks reunion). Besides Manuel Margot in Tampa, there aren't too many obvious CFs available in trade (the pitching-hungry, outfielder-laden Cardinals would have been a nice deal partner before they signed three free-agent arms in the last week).

Acquiring a corner outfielder should be simpler. Teoscar Hernández, Tommy Pham, Joc Pederson, Jorge Soler, Lourdes Gurriel Jr, Eddie Rosario and Adam Duvall are all legitimate upgrades over the current situation.

Bernie Williams discusses the Yankees' current state

2. Do they remedy the infield logjam?

Even with the departures of Kiner-Falefa and Josh Donaldson, the Yankees still have five infielders for four spots. Anthony Volpe had a roller-coaster rookie season, but made improvements as the season went on and will be the Opening Day shortstop barring unforeseen circumstances. LeMahieu was definitively average in 2023 and is under contract for another three seasons. Gleyber Torres, who saw the bulk of time at second base, will earn around $15 million in arbitration this year before hitting free agency next winter. Anthony Rizzo struggled and missed time with a brutal concussion, but should be the everyday first baseman. Top prospect Oswald Peraza was the front-runner for the shortstop job this past spring, but was Pipp'd by Volpe. That led to a lost season for Peraza as he never received consistent playing time in the bigs.

Injuries are inevitable, but if the Yankees want Peraza to be a starter, they have to clear a path for him. Whether that means a Torres trade or finding someone to take the LeMahieu salary, that's the most realistic option to ensure Peraza sees time at the big-league level.

3. Is there any shake-up in the pitching staff?

The Bronx Bombers were more like the Highbridge Hurlers in 2023 (sorry, that joke sucked). Despite horrendous contributions from Luis Severino and Rodón (the pair had a combined 6.74 ERA last year in 153 2/3 innings) the Yankees rotation ranked in the upper half of most categories. Much of that was due to the phenomenal season from Cole — whose combination of dominance and consistency earned him his first Cy Young — while solid performances from Clarke Schmidt, Michael King and Jhony Brito helped the overall numbers, too. 

Unless the Yankees add another veteran depth arm in free agency, a definite possibility, they'll enter 2024 with a rotation of Cole, Rodón, King, Schmidt and Nestor Cortes, who struggled with injuries for much of 2023. Any type of bounce back from Rodón makes this a solid rotation, especially if you include high-level depth pieces like Brito, Randy Vásquez and Clayton Beeter. They could probably use one more reliable arm, but for the most part this group is good enough, especially with a beast like Cole leading the way.

4. What happens at catcher?

Catchers are like sunglasses; you can buy a fancy one, but they could break at any moment. If you're careful, and/or lucky, you can keep a nice pair of shades for a while, but chances are the dangers of the world (your butt) take their toll.

Right now, the Yankees have four pairs of sunglasses, none of which are Gucci: Kyle Higashioka, Ben Rortvedt, Jose Trevino and Austin Wells. And like most normal human beings are with shades, the Yankees should really only have two catchers on their MLB roster. Trevino feels like the lock to start on Opening Day; he missed the last two months of ‘23 with a torn ligament in his wrist but remains the best defensive option and hit enough to warrant an All-Star selection in 2022.

Besides that, it's a mystery. Wells provides the most offensive upside and drew some positive reviews on his receiving, but has the flimsiest defensive reputation. Higashioka has experience and tenure, but lost the trust of his longtime buddy Cole, who now prefers to throw to other backstops. Rortvedt missed tons of time with various injuries and then didn't hit in a brief sample.

5. Do we see any internal shake-up?

No team in MLB receives more outside scrutiny than the Yankees. That comes with the territory, 27 rings, enormous media market, larger international footprint than half the league combined, etc. That being said, the disorganization in the organization was real at times this past season. Owner Hal Steinbrenner spoke publicly, multiple times, about the need to shake things up. Besides a new hitting coach and a replacement bench coach for the departed Carlos Mendoza, that hasn't happened so far this winter.

Perhaps the club evaluated itself and preferred the status quo. Perhaps it's more aimless than that. Any decision the Yankees make, even a non-decision, is news. Cashman has held the top spot in the Bronx since 1998 and seems to have a rock-solid rapport with his owner, but another disappointing season could heat his chair up for the first time in a long time.

Jake Mintz, the louder half of @CespedesBBQ is a baseball writer for FOX Sports. He played college baseball, poorly at first, then very well, very briefly. Jake lives in New York City where he coaches Little League and rides his bike, sometimes at the same time. Follow him on Twitter at @Jake_Mintz.

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Jake Mintz