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My Offseason Plan for the Yankees: Andy Singer

By Andy Singer

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Photo Credit: Jason Miller - Getty Images

Photo Credit: Jason Miller – Getty Images

I have spent the early days of the offseason debating the relative merits of a variety of hot stove debates. While I’ve publicly posited my opinions on some of those ideas, I really haven’t yet defined my vision for the 2020 Yankees more broadly. While it is important to really dissect the many facets of some of the decisions the Yankees face this offseason, I am (for once) just going to lay out my vision for what an ideal offseason would look like for the Yankees in very broad terms. The devil, of course, is in the details and I will expand on many of these ideas throughout the offseason. For now though, I want to define what I think the 2021 Yankees should look like.

Where the Yankees Stand Today

The Yankees are nowhere near as bad or as flawed as many of the tabloids would lead you to believe. Yes, the 2020 Yankees underperformed relative to expectations. Sure, I’d love to see some more lineup balance. The rotation with which the Yankees went into the 2020 season was not the one that limped to battle in the playoffs. Yet again, the 2020 Yankees were banged up constantly.

But we need to look at the big picture. The 2020 season was 60 games long. That’s less than 40% of the length of a standard season. No, a larger sample size wouldn’t have made Gary Sanchez a good catcher in 2020, but we can safely assume that a longer season would have meant that the Yankees would have been able to utilize the likes of Aaron Judge, Giancarlo Stanton, and maybe even the real James Paxton for a far higher percentage of their games. With a longer season, maybe Torres would have gotten totally healthy and found the hot streak that eluded him all year. Sure, that’s a ton of maybes, but over a larger sample size, we would expect guys to play closer to the back of their baseball cards.

The 2020 team disappointed, but the core of the Yankees is still a really good team that is supplemented by a plethora of good, young talent. The Yankees are not in need of an overhaul, but targeted supplementation would go a long way to helping get the team over the hump.

The 2021 Rotation

James Paxton, JA Happ, and Masahiro Tanaka are Free Agents. That leaves the following guys as possibilities for the rotation:

Gerrit Cole

Luis Severino (likely out until June/July following TJS)

Jordan Montgomery

Deivi Garcia

Domingo German

Clarke Schmidt

Mike King

Jonathan Loaisiga

Miguel Yajure

After Gerrit Cole, there are a lot of question marks, admittedly. Sevy is out until at least June/July 2021, and while too many people assume that pitchers will return from Tommy John Surgery without showing ill effects, the reality is far murkier. I won’t get into the Sevy conversation right this minute, but even despite the looming possibility of complications from Tommy John Surgery, I think that many Yankee fans have forgotten just how much the Yanks missed Severino in 2019 and 2020. A healthy Severino was an ace on all but maybe the top 5 teams in the league. Even a slightly diminished Severino is a fine Robin to Gerrit Cole’s batman, a dimension that the 2020 rotation was sorely lacking. Even if the 2021 Yankees have to wait a bit for Cole and Severino to pitch back-to-back, I expect the duo to be among the most valuable 1-2 punches in the Majors for the second half of 2021.

I am significantly more bullish on Montgomery’s projection than likely the rest of the community of baseball writers. Monty’s increased velocity, command with multiple pitches, and ability to provide different looks from start-to-start make him very projectable. Monty was one of the players hurt by a short season, such that one or two bad outings really tanked his overall numbers in a way that made his performance look far worse than it really was. While I wouldn’t call Monty someone who can be counted on for length, I think as a 5-6 inning starter, Monty can be a very good #3 or #4 starter.

As all of you who have been reading my work on SSTN for the last 2 years know, I am a huge Deivi Garcia fan, and I was really impressed by his performance in 2020 in light of the fact that he really didn’t get the additional development time in AAA that he would have gotten in an ideal world. Despite that, I think the Yankees will be able to give him a longer leash in 2021, and he should reward them with mid-rotation performance with occasional flashes of brilliance.

Despite all of the positives I list above, that still leaves the Yankees with 1-2 rotation spots to fill even before we start talking about the injuries that will surely occur throughout the year. So, here’s what I would do:

1.) Re-sign Masahiro Tanaka

The Yankees need someone who can be counted on for 175+ innings of competent performance. The Yankees know what they’re getting with Tanaka, and there is huge value to getting a known entity as a safety blanket in the rotation. Tanaka is that guy. Selfishly, I hope that his last two starts in a Yankee uniform are not what we saw in the 2020 playoffs.

2.) Sign Mike Minor

No, this is not a flashy move, and Minor was not good in 2020. However, Minor has a significant track record of successful pitching, putting up a 3.84 ERA since 2017 while striking out nearly a batter per inning. Most importantly, Minor comes with the flexibility that comes from experience pitching out of both the rotation and the bullpen, most recently pitching out of the bullpen in 2017 with the Royals.

Minor gives the Yankees security. If the pitching staff struggles or sees 2019 and 2020 levels, Minor is there to fill out the rotation and provide solid innings. If the young guns step up, Minor can fill the Ramiro Mendoza swingman role. Pre-Sevy, the rotation looks like this:

Gerrit Cole

Masahiro Tanaka

Mike Minor

Jordan Montgomery

Deivi Garcia/German

With Sevy:

Gerrit Cole

Luis Severino

Masahiro Tanaka

(5.) Monty/Garcia/Minor/German

In either scenario, that’s a competitive rotation that is likely one of the better rotations in the American League, with upside to be much better. No, I’m not spending my money on Trevor Bauer (we’ll talk more about that on a future day), but I think this is a good rotation over the long haul.

The Bullpen

The bullpen was more fallible than we’ve seen it in years in 2020. Going into 2021, here’s what the current bullpen looks like (I’m only going 10-deep for now):

Aroldis Chapman

Chad Green

Zack Britton

Adam Ottavino

Jonathan Holder

Jonathan Loaisiga

Nick Nelson

Luis Cessa

Ben Heller

Albert Abreu

The bullpen is as thin as it seems. To be fair, it is likely that one or two of the guys I mentioned as rotation possibilities could see significant time in the bullpen where their stuff could play up, but that shouldn’t be assumed unless the Yankees were to commit to real innings for some of the kids that aren’t long-term rotation pieces (as much as I’ve advocated for this, I don’t think the Yankees will do it). The Yankees really missed Tommy Kahnle this year, and Ottavino’s struggles made the bullpen thinner than anyone expected.

I’m not a believer in either Holder or Ottavino. Holder just isn’t very good, and while Ottavino has some wicked stuff, I’m just not sure he can be counted on to harness it consistently. I think it would be reasonable to move on from Holder. Ottavino is harder because of the contract, so for the sake of reality, I won’t say that the Yanks will move on from Ottavino, but if the opportunity presents itself, they shouldn’t hesitate to move on.

In a tough Free Agent market, we’ve already seen teams dump high-end relievers with 8-digit salaries (see Hand, Brad). I don’t expect it to break the bank to acquire 1-2 good relievers this offseason, and that is exactly what I would do. Personally, I like a 1-2 year deal for Trevor Rosenthal and Blake Treinen most among Free Agent relievers, but I’m perfectly fine with Brad Hand, Liam Hendriks, or former Yankee Shane Greene. The Yanks need depth and an expectation of performance, and 1-2 of these Free Agents would bring that.

Position Players

Everyone knows the Yankee position player roster by heart at this point, so I’m not going to run through each position individually. The primary issues we need to deal with are as follows (in no particular order):

DJ LeMahieu’s Free Agency

An inflexible, right-hand heavy lineup



DJ LeMahieu’s Free Agency

Let’s start with DJ LeMahieu. I love DJLM. Every time I watched him play, I liked him more. I heard from Colorado fans that I would love LeMahieu as a Yankee, yet somehow he surpassed every plausible scenario I imagined in my head. LeMahieu was the rare Free Agent that significantly outperformed his contract. While LeMahieu is on the backside of his prime, I think that it is likely that he still has at least 2-3 solid seasons left before his decline is significant enough to become a real problem. However, at $20+ million per season, he’d likely be less of a bargain than he was in 2019 and 2020. And there’s the rub: the Yankees have cleared a significant chunk of salary this offseason, and it makes sense to use that money on talent that is likely to be of greater value in both the near-term and long-term. The probability is that even though LeMahieu will continue to be a good player, possibly even great in 2021, we’ve already seen his best baseball. I won’t be upset if the Yanks re-sign LeMahieu – far from it. He should still be pretty darn good! But, I think the Yankees can do better.

An inflexible, right-hand heavy lineup

If LeMahieu isn’t re-signed, that leaves one spot for either a switch hitter or a left-handed bat. Beyond that though, I expect the starting lineup to look very similar to what we saw this year. Lineup balance is important, but not at the expense of talent. I see a lot of people who seem itching to “sell high” on Luke Voit, for example. Voit will be cheap right through his prime years, and is likely to put up offensive numbers that are commensurate with elite first basemen. Sure, he’s right handed, but that matters less when the player is that good. I’m riding with Voit in 2021 and beyond.

Same goes for Judge and Stanton. Judge is part of the team’s core, and the injuries he’s sustained in recent seasons are more of the bludgeon variety than of the structural variety. Judge will finally get a normal offseason to train coming into 2021, and I fully expect him to remind the league that court is in session whenever he steps on the field. Stanton reminded everyone what he can do when he’s locked in during the playoffs. Whatever we think of his contract, it’s basically untradeable. Stanton is another guy who can finally have a normal offseason (his first full offseason with the new training staff, I might add), and has the potential to relive the 2020 playoffs over a greater sample size in 2021.

So, how can I achieve lineup balance? Realistically, the Yankees need to be able to keep their guys fresh in an attempt to keep everyone healthier than they’ve been in recent seasons. One way to ensure this is to acquire more viable left-handed depth that can be counted on to either spell guys at multiple positions or even platoon, where appropriate.

Here are four Free Agents that could be of interest:

Brett Gardner OF

Jackie Bradley Jr. OF

Joc Pederson OF

Jurickson Profar UTIL

Brad Miller UTIL

We know Gardy, so I’m not going to get into it other than to say if Gardy is willing to accept a 4th outfielder role, he should have it. JBJ may be able to snag a starting CF job elsewhere, but the other three should be relatively easy to snag. Pederson has a history of success as a left-handed batter with pop against right handed pitching; Profar is a switch hitter who can play all over the diamond, and may yet have some untapped potential as a former blue chip prospect whose early career was haunted by a serious shoulder issue; and Miller is a former Yankee who has consistently hit right handed pitching with pop while playing all over the diamond. All of these guys should be relatively affordable.

Now to the good stuff. Here are a few of trade targets that I would look at:

Edwin Rios 3B/1B/OF

Ian Happ OF/2B

Johan Camargo UTIL

Some guy named Lindor

Rios and Happ are starting caliber players, though Happ is more established. Rios has huge raw power, high (but improving!) strikeout rates, and a history of good performance in the minors. We don’t know what the Dodgers plans are for 3B this year, but if Turner returns, Rios could be expendable. The likelihood is that the Cubs are going to look to shake-up their roster this Winter, and of the guys that are movable, I like Happ as a switch hitter that can match-up no matter what. Camargo is a good defensive ballplayer who has a history of being able to hit a bit, but has struggled the last couple of years. He can play all over the infield, and at his best, makes contact and draws walk with enough pop to be valuable. We’ll deal with Lindor later.

Ideally, I think if the Yankees add 2-4 guys from either of these buckets, the roster is significantly deeper than the roster the team brought into 2020 and it is capable of matching up with both lefties and righties.


I know that the torches are lit and the pitchforks are sharpened. Even I, a noted Gary Sanchez apologist, am questioning my faith in Sanchez’s ability to ever hit consistently enough to justify allowing him to eat at-bats behind the plate. However, I think it is going to be really hard to find catching that can be expected to outperform the combination of Sanchez and HIgashioka in the non-Realmuto division.

And while we’re here, I’ll reiterate that I don’t want Realmuto on a long-term deal. He’s great now, and 100% the best all-around catcher in the sport…now. Realmuto has multiple lower body injuries in his past and will be 30 years old at the start of 2021. I just don’t think that makes sense. Here are some of the other Free Agents available:

Yadier Molina

James McCann

Robinson Chirinos

Austin Romine

I love the idea of combining Molina with Sanchez, but I think that’s more fantasy than reality. I really don’t think Molina is leaving St. Louis. Beyond that? No thanks. I’d be skeptical of the rest of this group if they were backing up Higgy or Sanchez.

Like it or not, Sanchez still has upside, as does Higgy. For one more year, the Yankees will roll with Sanchez and Higashioka behind the plate.


I’ll save you the suspense: I’m moving Gleyber Torres back to 2B. It’s not that I don’t think Gleyber can play SS – in fact, I think Gleyber’s arm and hands would be good enough in time to make him either a slightly below-average or average defensive shortstop (which would be impressive given his lofty offensive projection). However, Gleyber’s lower half has gotten thick enough as he matures that I think his best position long-term is likely off of SS.

The best SS in baseball is available, and Cleveland remains intent on tanking their leverage in every way possible. I am in the camp that believes the Yankees should do their best to trade for Francisco Lindor, and then sign him to a massive extension. In last week’s mailbag, I threw out the following trade proposal: Clarke Schmidt, Miguel Andujar, Oswald Peraza, and Ezequiel Duran for Francisco Lindor. I admit, that feels light, but that’s balanced out by the leverage Cleveland has lost. At the very least, it’s a starting point for a deal, as I believe the Indians have signaled that they are firmly in rebuilding mode (or should be, at least). If it required Frazier to get the Yanks over the hump? As much as I like Frazier, I’d be inclined to rework the deal above to squeeze him in, within reason. Lindor is good enough to really go for it.

My ideal Yankee lineup looks like this:

C Sanchez/Higashioka

1B Voit

2B Torres

3B Urshela

SS Lindor

OF Judge

OF Hicks

OF Frazier

DH Stanton

Bench 1: Camargo UTIL

Bench 2: Gardner/Bradley Jr. OF

Bench 3: Rios 1B/3B/LF

This is a lineup that could compete with anyone. It would be an expensive bench, but if the last two seasons have proven anything, it’s that the Yankees need 2nd…and 3rd options where possible. Realistically, I think someone like Brad Miller would be far more likely than, say, Rios in that final bench spot. I also am fine with jettisoning Wade and Tauchman.


The above represents a general blueprint for the offseason, and will hopefully help frame my thinking when I write about many of the concepts, trade possibilities, Free Agents, and lineup moves throughout this offseason. Most of the real money goes to Lindor and the bullpen, though I think both the rotation and the team’s depth can be supplemented without breaking the bank.

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