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Looking Ahead to the 2021 Yankees – My Approach To The Off-Season, Part 5: Looking at the Star

In the previous installments of this series, I have made the following suggestions:

Keep Brian Cashman as the GM

Keep Aaron Boone as the manager, but hire an old sage as his bench coach

In a previous post, I demonstrated that the team has too many right-handed hitters and that, historically, the Yankees have never won a World Championship without left-handed power.

Next, I made the argument that Anthony Rizzo could be available and would fit well at first base.

Then I opined on who should play leftfield.

I then looked at the catching position.

Today we’ll finally get to the starting rotation.


The Yankees need starting pitching. They need it desperately. To date, they have one reliable starter. One. Uno. This is not the way to head into a season that fans hope brings them a championship.

The good news is that the Yankees have an ace at the top of the rotation. That’s a great start, but completing this staff will not be easy. The Yankees are in desperate need to add arms to support ace Gerrit Cole.

Since the close of the 2020 season, Masahiro Tanaka, James Paxton, and J.A. Happ have all become free agents. This is bad news in that it leaves the Yankees’ rotation almost empty, but it is good news in that a ton of salary has come off the books. This money could easily pay the salary of Trevor Bauer who is, by far, the best pitcher on the free agent market.

As always, I love seeing the Yankees going all-in and using their financial strength to bring in the best talent year-after-year. Trevor Bauer represents that. By signing Bauer, the Yankees would be making the statement that they are all in for 2021 and beyond. It would be difficult to argue against signing Trevor Bauer.

But I wouldn’t do it.

Maybe this deserves a more detailed post, but, there are two main reasons why I would not sign Trevor Bauer as part of the plan I have articulated thus far:

While I love seeing the Yankees spending big, I have to also recognize that they must operate with a budget. Looking at the team I have created in this exercise (see below), I have spent a large chunk of that budget in my quest to acquire the very best shortstop in the game and address the Yankees’ need for lefty bats in the lineup.

I am always less than enthused about signing a pitcher (or any player) coming off what was, by far, that player’s best season. Trevor Bauer was great in 2020. He hasn’t always been great. I would not invest the $25-30M it would cost annually to sign Bauer. That seems like too big a risk. It’s a hard pass.

The general narrative, though, is that outside of the biggest of the free agents (D.J. LeMahieu and Trevor Bauer to name two of the biggest), the market might be slow and favor the teams rather than the players. There is a lot of talk that the market will drag down salaries. It should be a buyer’s market. This is good news for my rotation. I believe the Yankees can get some quality arms at discount prices.

With that in mind, after much consideration, I think it is best to go with what is known. Two of the Yankees’ three free agent pitchers will probably come at vastly reduced salaries compared to what the Yankees spent in 2020. If they can be had for no more than three years at no more than $12M annually (3 years/$36M), I would bring back both Masahiro Tanaka and James Paxton. I would, of course, prefer to bring them back on two-year deals – especially Paxton. For two years, I’d be willing to go as high as (2/$30M). Both of these pitchers have frustrated me at times over the years as I have expected more from them, but they are each quality arms, and if healthy (Paxton) could be among the best bargains in the game. Tanaka knows how to pitch, has succeeded in New York, and should have a number of quality years ahead of him. (Of note, I still believe that J.A. Happ will pitch well into his 40s, but I also believe that his success will come outside of New York. I would not bring J.A. Happ back.)

For this exercise, let’s assume the Yankees are able to bring back one of James Paxton or Masahiro Tanaka. (We don’t always get everything we want.) I would slot that pitcher as my #3 starter. One of the Yankees’ flaws these last few years has been expecting pitchers like Paxton and Tanaka to be #1 or #2 starters. They aren’t that. But, as a #3 starter, they should each be fantastic.

For my #5 starter, I look to the long-shot candidate. The best pitcher in this category who is out there is, by far, Corey Kluber. Kluber is supposedly healthy after suffering from arm troubles and injuries. If he is healthy, he would be a steal. I wouldn’t hesitate to take a chance on Kluber and would slot him in at #5. I would even give him a two-year deal to get him to the Yankees with the hope and promise that his 2022 season would be even better than 2021.

The insurance for Kluber is that Luis Severino should be back by mid-season. Severino is an exceptional talent, still possibly a future ace, but he has not been great since the first half of the 2018 season which was a long time ago. If he’s healthy, he’ll fit right into the rotation. I can slot him in as the #5 pitcher if Kluber washes out in the first half. But, here’s the beauty of this. While Severino is my Kluber insurance, Kluber is my Severino insurance. If Corey Kluber pitches well, he would be slotted higher in the rotation allowing Luis Severino to come back slowly at the back-end of the rotation. The Yankees have too much invested in Severino and his talent is too great to rush him. I would bring Luis Severino back very slowly, again looking more to 2022 (and beyond).

To begin the year, my #4 starter would be Deivi Garcia. I am very high on Garcia (as are most). He could also be a top-line starter in the near future. For the 2021 season, he would pitch regularly to begin his big league career in earnest. But he would pitch at the back-end of the rotation.

All of the above leaves the critical (and essential) #2 spot wide open. Wide open. While I believe Masahiro Tanaka (or James Paxton), Deivi Garcia, Corey Kluber (and Luis Severino) will pitch well in 2021, the Yankees still need a quality starter to match with Gerrit Cole at the top of the rotation – especially come playoff time.

Because I have the rest of the rotation in order, I now have a great collection of highly valued pitchers who could be packaged for a legitimate #2 starter. Among these pitchers are Jordan Montgomery, Clarke Schmidt, and Domingo German. I think any two of these pitchers, along with a lower tier prospect, could fetch a quality pitcher. The pitcher who doesn’t go in a deal would be the Yankees #6 starter/swing man/ Deivi Garcia insurance.

I speculated a few weeks ago that the Phillies might realize that their window has closed. Their owner has supposedly lost boatloads of money. They may need to cut costs. They are shopping Zack Wheeler, but he is too expensive. Might the Phillies make Aaron Nola available in a package for Montgomery, Schmidt, and one other young arm? A deal like that would be hard to pass up and for my scenario, I am going to assume that the Phillies agree. Aaron Nola slots in as my #2. (If not Nola, I am certain my package would net a quality arm.) I’ll assume that Montgomery and Schmidt are the pitchers that are traded.

My back-up plan to the big trade, which I don’t love, would be to move Tanaka/Paxton to the #2 starter and sign one other of the plethora of starting pitchers who have all once enjoyed great success and could bounce back. Since it’s a buyer’s market, any of the following could come to the Yankees at a very reasonable price: Jon Lester, Jose Quintana, Jake Odorizzi, or Jake Arrieta (and that is the order in which I would pursue these pitchers).

The only aspect of my rotation that I don’t love is that it is all right-handed (assuming James Paxton and/or Jon Lester – both back-up plans) don’t come to the Bronx. I am loathe to build a Yankees’ staff that is without left-handed starters, but in this case, I don’t see an alternative.

I would rectify this by acquiring some lefty arms (and plenty are available) for the bullpen.

With the starting staff as outlined above, I feel I have built a 2021 Yankees team that is poised for a World Championship.


The following are my 2021 Yankees:

1B – Anthony Rizzo

2B – Gleyber Torres

SS – Francisco Lindor

3B – Gio Urshela

LF – Aaron Hicks

CF – Jackie Bradley Jr.

RF – Aaron Judge

OF – Clint Frazier

DH – Giancarlo Stanton

C – Gary Sanchez/Kyle Higashioka

BENCH – Shin-Soo Choo

SP – Gerrit Cole

SP – Aaron Nola

SP – Masahiro Tanaka or James Paxton

SP – Deivi Garcia / Domingo German

SP – Corey Kluber / Luis Severino


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