The 2021 season can only be looked back on for the New York Yankees with sheer disappointment:

• They were heavily favored to run the table in their division…and barely finished third
• They had a healthy Judge & Stanton…and were middle of the pack in run production and slugging
• They had Gerrit Cole pitch in 31 games…and watched him unravel in the latter 10 including the playoffs
• They were supposed to have a roster built for October…and got bounced in the Wild Card Game

Now the Yankees enter the 2021-2022 Offseason with a lot of things to figure out and the eyes of the baseball world fixated on what comes next. So that is exactly what I’m trying to do here, in a little series I’m calling “The Offseason Dissection”. In an effort to examine what the Yankees have now, and where they need to be come opening day of 2022, I’ve broken this team down position by position. I’ll talk who needs to stay and who needs to go. So with out further a do, let’s begin with the man who’s job that actually is:

Front Office

The Yankees’ front office has been helmed by Brian Cashman for the entirety of this millennium. He’s never seen the Yanks have a losing season; yet he’s seen them grossly underperform in the biggest of moments and pale in comparison to the rival Red Sox for the first time since the early 1900s (pre-Curse of the Bambino).

There’s growing vitriol amongst fans, and a seemingly ever-expanding media crusade to oust Cashman from his job as the longest-tenured General Manager in baseball today. While things do need to change, I fall into the line of thinking that its better to enter this retooling era of Yankee baseball with the devil you know.

New Yorkers watched Cashman turn the team around in the post-Core Four era just a few years ago, ushering in a new wave of burgeoning superstars like Aaron Judge and Gary Sanchez to pair with consummate professionals like Brett Gardner and CC Sabathia for a pair of 100-win seasons and a would be World Series appearance if not for the Astros’ sign-stealing scandal. What I’m saying here is that you know he can do the job to field a competitive team, and it isn’t quite time to blow the whole thing up just yet.

Coaching Staff

To keep or move on from Aaron Boone has been a hot-button issue since the All-Star Break this year, and to be frank I don’t know that it really matters. Boone as a manager in many respects is the result of a modern-day sports philosophy that champions on-paper statistics over eye-test intangibles. He’s not alone in this by any means, but essentially he’s simply a middle man for the analytic nerds behind the scenes and the athletes carrying out the game plan on the field.

Would it be fun to watch Buck Showalter return to the clubhouse in the Bronx to unleash hell on Sanchez for not running out a grounder or on Joey Gallo for striking out for the 200th time that season? You bet! But is it really the likely option for a hire from a front office who wants to be in complete and utter control of how their squad is lined up? Not at all.

So the question becomes, do you keep the puppet you have or string up a new one? And to be completely honest I think the biggest benefit of Boone sticking around is that we’ll at least get to keep watching video packages containing his 2003 ALCS-winning home run (coincidentally the last meaningful victory the Yanks have against the Red Sox).

Starting Pitching

As it appears on paper right now, the New York Yankees are slated to role out the following rotation in 2022: Cole, Luis Severino, Jameson Taillon, Jordan Montgomery and Domingo German. On paper it certainly isn’t anything to sneeze at, but given the necessity of having a multitude of big game pitchers in the modern playoff structure it can definitely use some upgrading. Throw in the fact that all but Cole have had to miss significant time in recent years with injury-issues, and you don’t really have a recipe for sustained success here. So where do you find your improvements?

Internally the Yankees remain high on Luis Medina and Luis Gil, the latter of whom made a worthwhile impression in half a dozen spot-starts in the second half of 2021. But still, unproven rookies hardly move the needle in the capacity that the Yankees need it to. So the first look goes to the top of the free agent class this year. Max Scherzer, Kevin Gausman and Robbie Ray are likely to command a healthy dollar over a short term deal, the latter of whom the Yankees have been linked to since his days constantly circling the trade market while with the Diamondbacks. But it might not be in the Bombers’ best interest to throw all their lunch money in on any of them considering how much other work needs to be done.

So now we look to the trade market, and the Yankees have a choice to make between Gio Urshela and Gleyber Torres. Torres, just 24, currently has the lowest trade value of his professional career given he grossly underperformed in the past two seasons. It would be almost criminal to move on now, knowing that even if you hold out until the All-Star break his stock could rise exponentially once more with a strong start. Gio on the other hand is riding higher than ever, despite an injury plagued 2021. He along with a couple of mid-tier prospects very well could net the Yankees something special in the trade market. Right now, I’d be engaging in a borderline harassment of the Brewers’ front office for one of their trio of All-Stars (Corbin Burnes, Brandon Woodruff or Freddy Peralta). Their disappointing playoff exit should reveal that they need more stable lineup production, and a trade for Urshela could net them just that. As alternatives, make calls to the Rockies about German Marquez, the A’s about Chris Bassitt, the Phillies about Aaron Nola and the Reds about Luis Castillo.

Bullpen

Yankee fans’ patience is wearing thin with Aroldis Chapman, Zack Britton and Chad Green. Unfortunately though, their fairly hefty salaries are going to likely keep them tethered to the Bronx for at least one more year. Jonathan Loasiga was an absolute revelation (perhaps not to the extent that Alex Rodriguez believes…but still good), and guys like Lucas Luetge, Nestor Cortes and Clay Holmes have proven that they deserve a spot in the Yankees’ future plans. The Bombers lack a consistent late inning guy, and quite frankly with Chapman’s recent implosions its time to bring in a new closing option. Internally the Yankees have a slew of forgotten pitching prospects (Deivi Garcia, Clarke Schmidt, Nick Nelson and Albert Abreu) who have lost the luster as potential starters. So why not see what they can give you in condensed bullpen outings. The Yankees have started this with Abreu and Nelson, but shouldn’t be shy about seeing what a guy once deemed “mini-Pedro” can be if you let him just throw without a pitch count concern.

On the free agent market, the flashiest targets are going to be Matt Barnes and Kirby Yates. The former is likely going to get locked up in short-order by his current squad, the Boston Red Sox. The latter is coming off of Tommy John surgery at age 34, and even still is likely to stay with another division foe, the Toronto Blue Jays.

Luke Voit, the Yankees’ remaining most tradable asset comes into play here. Despite being plagued by knee injuries, teams have watched the spark his big bat can bring even when he has to limp around the bases. Rather than non-tendering him and letting him go for didly-squat, the Yankees should try their best to leverage him for a quality reliever with back-end potential. I was very big on Richard Rodriguez at the deadline, but he instead found a new home in Atlanta and is unlikely to be moved. So now I think the Indians’ Emanuel Clase and the Pirates’ David Bednar deserve to be circled on the Yankees’ check-in list. The former represents a young and exciting option with high-upside. The latter is a bit more seasoned and likely is nearing his ceiling, but has proven that he can inherit the 9th inning job without any statistical dropoff.

Catcher

I know what you’re looking for here, and it is with great sadness I must inform you that the Yankees will undoubtedly have to roll into 2022 with the two-headed nightmare of Gary Sanchez and Kyle Higashioka behind the dish. The Yankees have a pair of intriguing Catching prospects in the farm system in Austin Wells and Josh Breaux, but they remain some years away in terms of being MLB-ready.

The free agent market for catching is painfully thin, and a Giants resurgence this year means there’s no way they allow their franchise cornerstone, Buster Posey, to get a chance to test the free agent waters. The best available options at the moment appear to be Manny Pina and Yan Gomes, both of whom profile more as respectable backups at this point in their big league careers.

Trading for an elite backstop has always been a tall order in baseball, it’s a position with few talents who fit the bill and therefore the asking price is usually too much for any team to stomach. That holds true this year too in any estimation. The likelihood of the Yankees being able to wrestle JT Realmuto or Wilson Contreras away from their squads seems bleak at best, and fans would likely understand why when analyzing the asking price.

First Base

With the Yankees moving on from Luke Voit, the best option this winter is clear. Brian Cashman has a history of retaining mid-season rentals who fit well with the club’s needs and I don’t believe that he should change up that strategy when we’re talking about Anthony Rizzo. Rizzo fits the role once manned by Mark Teixeira during the Yankees’ last World Series run. He’s a Gold Glove caliber defender at first base, an on-base machine and when he’s hot he is one of the toughest outs in baseball. A two or three year deal for the now 33 year old Rizzo is ideal, and it gives them long term flexibility at the position, without being tethered to an post-prime player.

The only note-worthy internal option for the Yankees would be permanently moving either DJ Lemahieu or Joey Gallo over to First Base. Both are definitely do-able but their talents are needed elsewhere for the time-being.

The free agent first base market is set to be as bare-bones as the catching market, short of CJ Cron who represents a similar profile as Luke Voit who clearly wasn’t the right fit here. On the trade front, Matt Olson of the ever-selling Oakland A’s is worth a nice long look, but knowing he’s due for a pay day at the same time as Judge, Sanchez, Severino, Gallo and Green makes him a probably over-priced one year rental.

Second Base

Let’s be real, the Yankees probably shouldn’t have moved Gleyber Torres to shortstop but it was a situation that nobody could have expected to go as badly as it did. Now that he’s back to playing second base on a permanent basis things appear to be going swimmingly. Gleyber made a slew of impact plays defensively down the stretch for the Yanks and his bat seemed to come alive with the burden of shortstop being removed from his shoulders.

He’s young enough still to warrant the Yankees remaining high on him, and despite dips in production over two seasons you have to assume a 24 year old is hardly at the end of his rope, especially when he is still 3 years away from free agency. It costs little to keep him in the face of overpaying a free agent like Marcus Semien or Jonathan Schoop to do the job, and in a worst case scenario he acts as a stop gap until the many middle-infield prospects that the Yankees have hoarded recently are big league ready in the coming seasons.

Third Base

I’ve got the Yankees trading Gio Urshela for pitching, so the third base job falls squarely to DJ Lemahieu. LeMachine had an uncharacteristically down year, something many Yankees can relate to, but he finished top 4 in MVP voting for two consecutive seasons since arriving in the Bronx before that.

This job is 100% DJ’s for at least the next few years, when in all likelihood he’ll either be relocating to First Base when the Rizzo extension expires, or back to his home at Second Base when Gleyber Day in the Bronx comes to a close.

Shortstop

Now this is one of two places where the big move in the Bronx has to be made. The Yankees haven’t had shortstop stability since Derek Jeter (I loved Didi Gregorious but he spent a lot of time on the IL), and they need to buck the trend sooner rather than later. There’s a case to be made for piece-mealing a shortstop rotation from Andrew Velazquez, Tyler Wade and a bargain basement free agent like Jose Iglesias or Freddy Galvis until your prized prospects are ready in a year or two, but I think the Yankees have to be substantially more aggressive in this case.

The free agent market is set to be short stop heavy, and the Yankees need to take a stab at signing one of the major targets here. Carlos Correa is perhaps the best available option, but he’ll be inundated with big money offers from the likes of the Astros and Mets. Trevor Story was linked to the Yanks at the deadline this year, and very well could be a great addition this winter. I like Corey Seager the best as a fit for the Yankees though. His lefty bat will play well in Yankee Stadium, he’s a solid defender, he has a proven track record of playoff success and because the Dodgers now have Trea Turner they’re unlikely to resign Seager, lowering the bidding war for his services exponentially.

Long term here, whoever the Yankees can pull from that trio is likely to man the position for only a pair of seasons before ultimately being relocated to the hot corner as one of the minor league shortstops pushes through the system.

Outfield

This is the other spot for the Yankees to make a major move, with Centerfield in particular needing some big improvements. Starling Marte would be a great get here courtesy of the free agent market, but I believe the Yankees will have better luck piece-mealing the outfield successfully than they would shortstop.

When healthy, Aaron Hicks remains a serviceable Centerfield starter, his health though remains an issue and if history is any indicator we’re unlikely to see him appear in more that 70 games next season. Brett Gardner seems to have no intention of retiring prior to his contract expiring a year from now (despite my pleas) so while they’ve got him for now I guess they have to use him. Throw in high-energy options like Greg Allen and Esetvan Florial for spurts here too, and the occasional Gallo/Judge day when they aren’t anchoring the corners, and you’ve found about 162 games of potentially above-mediocre centerfield production. Hopefully its enough to bridge the gap to top prospect Jasson Dominguez in 2023.

Out on the corners, Judge continues to be the best Right Fielder in baseball not named Mookie Betts, and Gallo is a great defensive player in Left Field who is going to continue to do the whole walk/strikeout/home run thing when batting. Also, we have to see more Stanton in the outfield days in 2022. We saw his production soar when his job wasn’t solely to overanalyze his at-bats while waiting for the next one, and he’s hardly a slouch defensively. Oh yea and I guess Miguel Andujar and Clint Frazier are still technically a part of this two short of them being part of the trades I mentioned up top.

Designated Hitter

Quite simply the Yankees need to function for the foreseeable future without a regularly scheduled Designated Hitter in the lineup. Stanton will likely see the lion share of games here, but given the rationale above it’s for the best he gets a lot more time in a different spot.

The Yankees need to use this as an alternative-to-rest spot. Let Judge, Gallo and Sanchez prolong their seasons (and potentially careers) by taking a few days to focus exclusively on being the first guy to hit a baseball out of Yankee Stadium.

Plus when guys like Torres, Rizzo and LeMahieu need a day off in the midst of a hot streak, this spot can be flexible for them since there isn’t someone else being shoehorned into it. Heck when Frazier and Andujar give you there annual two-weeks of strong play, no need to sit ’em when their starting counterparts can take a day in the DH role.