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Eight Steps to Yankee Success in 2021

By Mike Whiteman

The Yankees’ 2020 season ended with the loss to Tampa Bay in the AL Division. This certainly isn’t where we thought they would be when pitchers and catchers reported to Spring Training, with the team showing off their new $324 million ace. With the sub-.500 Astros waiting to face them in the ALCS, I get a real feeling of opportunity lost. If just they could have squeezed out little more offense, it could be the Yankees moving on to the World Series, not the Rays.

Being so close would indicate that the Yankees wouldn’t need to do too much to return to this point next season. Alas, 2020 was a unique season, and a repeat performance won’t do, especially now that the Rays have established themselves as a force to be reckoned with for the near future.

The Yankees window for a championship is now, so decisions they make must emphasize the now, as opposed to the later.

With this in mind, here’s this armchair GM’s suggestion for 2021 prep. Note that I’m going with an assumption that there will be a budget imposed by ownership, so I’m trying to improve while being relatively cost efficient too:

1. The Yankees should sign Andrelton Simmons as a Free Agent – Yankee shortstop play was not good at all in 2020. While Gleyber Torres has the ability to develop to be an acceptable shortstop, we don’t have time to let this play out. Simmons has struggled a bit with injuries the past two seasons, but is a game-changer with his defense. He also brings some speed and has better than average contact hitting skills, both of which would be useful, and could be a solid number nine hitter.

There has been some speculation about a reunion with Didi Gregorius, and I’d be open to that as well, but if I had my way I’d go for Simmons for his advantage on defense. The significant upgrade of replacing Gleyber with Simmons would have a real positive effect on the pitching staff even if the Yanks made no other moves to the staff.

2. The Yankees should then move Gleyber Torres to second base – Torres hasn’t dazzled in the field at any position, but he has been better at second than shortstop. He’ll be 24 next season and has special hitting talent, so we hang onto him, but we plant him at second base.

3. Sign DJ LeMahieu to a 4-5 year contract and make him the first baseman – Might the Yankees need to go five years to retain the best player of the past two seasons? Maybe. The Yanks won’t be too excited about signing a soon to be age-32 second baseman to a long expensive contract, but LeMahieu looks to be the type whose bat should age well and could play first base capably for a long time. He’s not a masher, but the fact that Torres is, while playing second base, reduces the need for such a player at first. Replacing DJ with Gleyber at second does weaken that position a bit, but replacing Luke Voit with DJ strengthens the Yankees there.

So, here’s the Yankee infield in 2021:

1B-LeMahieu 2B-Torres SS-Simmons 3B-Gio Urshela

Three good defenders, with an elite one at the crucial shortstop position. Tyler Wade and Thairo Estrada can battle for the reserve role. As a bonus, for the near future, LeMahieu could move off of first in the event of an injury to Torres, Urshela, or even to Simmons (moving Torres to shortstop temporarily).

4. Re-sign Masahiro Tanaka – Right now the Yankee rotation is set up to be Gerrit Cole, Jordan Montgomery, Deivi Garcia, and well………. Tanaka is a known quantity and can handle New York. He’s not the ace he was brought in to be in 2014, but he can still handle a #4 starter role.

5. Sign Marcus Stroman – Stroman is considered by many to be the second best starting pitcher on the market after Trevor Bauer. I don’t think Yanks are signing Bauer. He would cost too much money, which is a Yankee concern these days, and I’m not sure if they want to add his outspoken manner to what has been a pretty peaceful/boring clubhouse. Stroman missed 2020 with a calf injury and his decision to opt out of the season. His arm though is seemingly sound and could slot as a #2 or #3 starter.

So, here’s my Opening Day 2021 rotation:

Cole Stroman Garcia Tanaka Montgomery Waiting in the wings are prospects Clarke Schmidt and Miguel Yajure, and of course Luis Severino, who’s recovering from Tommy John Surgery. Because you can never have too much pitching, if the opportunity to sign James Paxton or a rebound candidate like Jake Odorizzi to a club friendly deal presents itself, I’d be open to that as well.

6. Trades – Here are my tradable Yankee assets:

Luke Voit Miguel Andujar Gary Sanchez Jonathan Loaisiga Esteval Florial Chad Green Mike Tauchman Minor League Prospects

Now, I love Luke Voit. He’s a great story, and looks to be a pretty good guy. I hate to deal him. I do think his skill set – right handed bomber – is redundant on this team. Throw in his suspect defense and the fact that I’m not sure about his ability to keep healthy, and I see him as a trade candidate. Coming off a season as the Major League home run leader, his trade value isn’t going to be higher than it is now.

My trade targets: Kansas City catcher Salvador Perez and Texas outfielder Joey Gallo.

If the Yankees want to win now, they need to move on from Gary Sanchez. We know Sanchez is talented; really talented. In my opinion, he needs to be given a catching job in a low pressure environment and play every day though his struggles to get his confidence back. That place is not New York.

The 30-year old Perez is one of the premier catchers in the game; a six-time all-star, five time Gold Glover and two-time Silver slugger whose contract expires after next season and won’t be taking a pay cut. From all indications, the Royals aren’t shopping Perez but I suspect they would be open to a deal if approached. Along with a better fielding shortstop, a gold glove catcher with improving pitch framing skills (upgrade in 2020 over 2017/2018) also will make the Yankee pitching staff even better.

A first look at Gallo’s stats indicate another all or nothing masher, and he indeed has had two 40+ homer seasons and a career batting average of .208. There is more though to the 27-year old outfielder. He brings defensive flexibility to the team, having average/positive defensive numbers in all outfield positions and first base. He also brings massive left-handed power, which should play really well in Yankee Stadium. He can rotate through the outfield, mainly sharing left field with Clint Frazier, and first base, freeing LeMahieu to move to other positions as circumstances warrant.

I went to and ran multiple deals in their trade simulator for Gallo and Perez using the players listed above. They all were accepted by the simulator, which itself wouldn’t necessarily mean the deals would be slam dunks. I suspect the Yanks might have to dip a bit further into the minors to make a prospect haul worth it for their trade partners, but as they are in win now mode, they have to consider it. I actually think the Gallo deal would be bit harder of the two, as he really seemed to be in the midst of a breakout season in 2019 before injuries cut his season basically in half.

Should Brian Cashman follow my blueprint, here’s a possible Opening Day lineup in 2021:

Hicks, CF LeMahieu, 1B Judge, RF Stanton, DH Torres, 2B Perez, C Frazier, LF Urshela, 3B Simmons, SS

Not bad, especially with the ability to rotate Gallo into the outfield, first base and DH.

7. Upgrade the Pen: The 2020 Yankee bullpen wasn’t the shutdown unit we’ve become accustomed to. Here are the holdovers to the Yankee bullpen: Chapman Britton Green Ottavino Cessa Holder Nelson Loaisiga Heller

Now, if the trades I listed happen, we could subtract a couple of players from this list. Even with that, this isn’t the worst bullpen in the world and can be upgraded relatively easily via free agency. If I’m Cashman, I’m targeting a couple of arms such as Blake Treinen and Justin Wilson, and maybe a “lottery ticket” like Wade Davis as a Spring Training invite.

Like a number of other pundits, I’m a bit bullish on Nick Nelson’s future in the bullpen. Take away his disastrous outing against the Phillies in August and he had a 2.37 ERA in 2020.

8. Invite Brett Gardner back – Because these are the Yankees, and injuries have dominated the scene the past two years, backup plans are needed for the backup plans. If the Yankees carry thirteen position players on the roster, that would include the lineup listed above, Gallo, a backup catcher (I think Kyle Higashioka would fill this role just fine) and either Wade/Estrada.

That’s twelve players – who would be the last? We know that the position where injuries have been the most devastating recently has been the outfield. Judge, Stanton, and Hicks all missed significant playing time in 2019 and/or 2020. As we don’t want a scenario like 2018 with an infielder like Neil Walker playing right field, I’d lean towards filling the last roster slot with an outfielder.

I’d suggest bringing back Brett Gardner.

Gardner of course brings his leadership to the table. That’s not all. Though his best days at bat seems to be behind him, he had a .802 OPS against right-handers, can still field his position and is a plus baserunner. This is fully intended to be a complimentary role, and if Gardner gets 400 plate appearances, we know that the season hasn’t gone well.

So that’s my plan. It’s my hope that with these moves the Yanks get a bit more balanced, a bit more flexible and a bit better defensively. All of these attributes can be the difference between success and failure in the postseason. Some difficult moves are made under this scenario, but this certainly isn’t an overhaul.

Yet there’s real pain in possible subtracting Sanchez, who just a couple of years ago was widely seen as a foundational part of the team and Voit, a Cashman find whose attitude I just love. As I said in my previous article comparing the 2020 Yanks to the 1995 version, sometimes taking that next step is painful, and not everyone who gets you to the threshold of greatness gets to take that next step.

What steps do YOU think the Yankees need to take to win it all in 2021?


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