Hal Steinbrenner
Kim Klement | USA TODAY Sports

As I write this, clouds cover New York as a steady rain falls and makes the scene in the Bronx even more somber. In fact, the feeling’s not too far off from how we felt when the Yankees’ season ended last year.

Another ALCS exit — this time a sweep — at the hands of the Astros, and the city is oddly calm. Nobody’s angry, upset, or even disappointed. The Yankees won 99 games despite almost blowing a 15.5-game lead in the division, and everyone’s just so depressed.

There’s a lot to take away from this year, including the futures of manager Aaron Boone and general manager Brian Cashman. Sorry to disappoint, but Boone has two years left on his contract and will be back regardless of his foolish excuses for losing games. Cashman’s contract is up, but more on that later.

In the meantime, the Yankees have a busy offseason ahead with lots of decisions to make no matter who’s in charge. Let’s start our 2022 season autopsy with every Yankees fan’s favorite subject, the payroll:

Yankees players under contract in 2023

Hal Steinbrenner has proven way more frugal than his father George, even as the Yankees had MLB’s third-highest payroll at almost $265 million. As a result, New York is in pretty good shape roster-wise for 2023. Giancarlo Stanton’s big bat will be back, and so will playoff sensation Harrison Bader. Here’s the fully guaranteed money for next season, per Spotrac:

  • Gerrit Cole: $36,000,000
  • Giancarlo Stanton: $32,000,000
  • Josh Donaldson: $21,000,000
  • DJ LeMahieu: $15,000,000
  • Aaron Hicks: $10,785,714
  • Harrison Bader: $5,200,000

Add it up, and that’s $119,985,714. There’s also a lot of potential for movement on some of these deals, which works since the Yankees have an Aaron Judge-sized task this winter.

Arbitration eligible and pre-arbitration players

Cashman deserves credit where it’s due. He’s the anti-Boss in that he understands the importance of youth, value, and the minor league system, so much that the Yankees have an astounding 14 players headed to arbitration. Thanks to the great team over at MLB Trade Rumors, we can guess what those 14 will earn in 2023:

  • Wandy Peralta: $3,100,000
  • Frankie Montas: $7,700,000
  • Isiah Kiner-Falefa: $6,500,000
  • Lou Trivino: $4,200,000
  • Gleyber Torres: $9,800,000
  • Clay Holmes: $2,900,000
  • Jonathan Loaisiga: $2,100,000
  • Domingo German: $2,600,000
  • Lucas Luetge: $1,700,000
  • Kyle Higashioka: $1,700,000
  • Tim Locastro: $1,200,000
  • Nestor Cortes: $3,500,000
  • Jose Trevino: $2,000,000
  • Michael King: $1,200,000

Now we add that to the guaranteed salary, and are at $170,185,714. There’s also plenty of potential to move some of these contracts, and Kiner-Falefa is a true non-tender candidate.

The Yankees are also swimming in pre-arbitration players with high ceilings. Ron Marinaccio was near-unhittable out of the bullpen before a shin injury knocked him out of the playoffs. Oswaldo Cabrera and Oswald Peraza could also potentially be high-impact players next year. And 2023 could also be when Estevan Florial’s potential finally manifests and Anthony Volpe makes his long-awaited debut.

It’s not the prettiest roster on paper, but it’s a testament that Cashman’s prospect hoarding can sometimes be a good thing. Not to mention, we now see the Yankees have serious financial flexibility heading into an offseason where they simply must re-sign Judge.

Yankees with player/team options

New York thankfully doesn’t have too much drama to deal with in this area. Only two players have these types of options, and one of them is a no-brainer.

  • Anthony Rizzo: $16,000,000 player option
  • Luis Severino: $15,000,000 team option

Severino’s option will certainly be picked up after his rejuvenant 2022. Add that to projected payroll, and we’re at $185,185,714. This is probably a good time to mention that MLB’s luxury tax threshold for next season is $233 million, so the Yankees are still in a good position.

Projected free agents

Even if Rizzo opts out, it seems less likely that it will be a traditional opt-out and more the CC Sabathia route. As in, his “opt-out” is really just adding years to his current contract at equal or slightly greater value.

That means the man of the offseason hour will be none other than Judge. Here’s who else is hitting the market with him:

  • Aaron Judge
  • Aroldis Chapman
  • Zack Britton
  • Chad Green
  • Jameson Taillon
  • Miguel Castro
  • Andrew Benintendi
  • Matt Carpenter
  • Marwin Gonzalez

Retained/deferred salaries

As of now, the Yankees don’t have any retained or deferred money on the books for 2023. That could change if one or both of Aaron Hicks and Josh Donaldson are moved in trades. They each had down enough years that with Donaldson making $21 million next year and Hicks having three years and $29.5 million left on his contract.

If the Yankees manage to move both without kicking in any money, it will be nothing short of an offseason miracle.

Current projected 2023 payroll

By our calculations, the Yankees are in pretty good shape from a money standpoint. If we assume Rizzo doesn’t opt out or negotiate an extension and simply add his $16 million, then projected payroll is at $201,185,714. Pre-arbitration salaries will raise it ever so slightly, but not enough to put New York over the Tier 1 threshold.

What happened during the 2022 regular season

The first two and a half months of the season were a literal dream for the Yankees and their fans. Cashman spurning Corey Seager, Carlos Correa, and Trevor Story in free agency for Donaldson and Kiner-Falefa looked like a genius move. Cut to July 8, and New York was 61-23 with a 15.5 game lead in the division despite losing Chad Green to Tommy John surgery and Joey Gallo’s awful hitting.

Nothing was ever the same afterwards, even as New York’s pitching stayed elite and finished third in MLB in ERA. The Yankees went 38-40 the rest of the way for multiple reasons. Bullpen stalwart Michael King injured his elbow, ending his season. DJ LeMahieu’s toe injury robbed him of his swing. A truly awful August to forget saw the Yankees go 10-18, their worst month since 1990.

It also didn’t help that despite their strong start, the Yankees still couldn’t beat the Astros. They went 2-5 against the once-again American League champions. Both wins only came at the mercy of walk-off hits.

Even so, the Yankees still finished 99-63 for their 30th straight winning season. The second-half near collapse was blunted by Judge swinging his way to a record-breaking season with 62 home runs. New York was also an amazing 57-24 at home compared to 42-39 on the road.

August was tough, especially going 4-6 on an important ten-game road trip. The Yankees overcame it all and still managed a good strong season.

What happened during the 2022 postseason?

The good news for the Yankees is because they had that 15.5-game lead on July 8, it was tough for the rest of the AL East to catch up. New York spiraled, and the other four teams just cannibalized themselves until the Blue Jays and Rays claimed two Wild Cards spots. Unfortunately for Toronto and Tampa Bay, both the Guardians and Mariners wanted the ALDS more.

The Yankees drew Cleveland, hit some home runs in five games, and that’s about it. A story throughout the series was how much better contact hitters the Guardians were compared to New York’s power. The Yankees’ nine home runs meant they won the series 3-2, but only batted .185 as a team.

This followed New York into its unfortunate ALCS rematch with Houston. The Astros’ pitching overcame a slow start by Justin Verlander in Game 1 and was no match for the Yankees’ flailing bats. Aaron Judge, after an MVP-caliber season, hit a paltry .139 with two homers and three RBI.

It was a sad end to a truly good season, one the Yankees really needed after underachieving all of 2021. Even as Donaldson, Kiner-Falefa, and even trade deadline acquisition Frankie Montas faltered, others thrived.

Judge made history not only with 62 home runs for the season, but the first walk-off home run of his career against Toronto in April. Nestor Cortes became the secondary ace to Gerrit Cole and took a no-hitter into the eighth inning one start. Harrison Bader hit five postseason home runs and proved he’s more than just a New York native who grew up loving the Yankees. He is a Yankee.

There’s absolutely room for the Yankees to run it back in 2023, but that depends on a lot of different things involving a lot of different people.

Yankees’ biggest decisions and needs for 2023

The Yankees have a Herculean task in re-signing Judge this offseason. Batting .314 with 62 home runs and 131 RBI means he’ll have plenty of suitors lined up. The San Francisco Giants have already implied their interest, so New York has their work cut out for them.

Yet, who’s going to negotiate with Judge? Remember how I said at the beginning that Cashman’s contract was up and we’d discuss it later? We’re finally at that point.

In a nutshell, Cashman needs to be completely gone from the Yankees. He’s had five years to build off of reaching Game 7 of the 2017 ALCS and what has he done with them? Signing Cole is nice, as are two trips to the ALCS, but let’s be real. From the prospect hoarding to decisions based on value instead of need, the writing is on the wall that the Cashman model is good for the regular season and not much else.

Just look at the rest of baseball. The Astros were marked for a slow death down the AL West standings after the cheating in 2017 came out in 2020. Not only have they made every ALCS since, but they’ve become an even better team. The AL East is only improving too, and the rest of baseball is running circles around the Yankees in terms of player development. Steinbrenner needs to step up and fire the only GM he’s known since taking over for his father.

But even then, who else can actually be trusted with the Yankees’ offseason to-do list? On top of re-signing Judge, the pitching rotation and outfield need to be addressed. Moreover, who besides Cashman can the Yankees trust to move Hicks’ contract and maybe more to bring the team one step closer to the World Series?

There are so many moving parts to the Yankees’ winter that it’s almost impossible to guess an agenda at this point, but we can all agree on a single truth. When you’re swept out of the ALCS and turn to the Red Sox to rally the troops?

Well, then pardon this writer for thinking winning 99 games in a season isn’t something to celebrate this time around.

Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.