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  • Cary Greene

More on "Poor Play and 2023"

by Cary Greene

August 30, 2022


If I ran the Yankees and they finish the season playing as poorly as they did in July and August, what changes would I make for 2023?

In my work-life, I’m a National sales leader and a high performance culture creator and team builder. Life has taught me to always look myself in the mirror before blaming others for a problem and most problems, probably more than 90% of them, start with the leader. Leaders need to own their piece of the problem before real change can happen. For this exercise, I will “pretend” that I’ve bought the NY Yankees from Hal Steinbrenner and as such, the first question I have to ask is, did Brian Cashman get enough guidance on baseball matters from Hal and was Hal willing to go all in and spend money commensurate with what it takes to win it all - competing as a large market team?

I don’t think the answers are necessarily yes on both of those counts, so blaming Brian Cashman or Aaron Boone for the failure would be unacceptable to me. Therefore, my first order of business would be to put a plan in place to help them succeed. Baseball is extremely competitive right now and without an invested team owner, one who can guide the organization, it would be very difficult to win a World Series. There are 30 teams in the league now and the playoffs, expanded to a larger format, make winning a World Series title all the more difficult.

In order to put the right plan in place, I’d need to surround myself with a trusted team of advisors and consultants and I’d meet with them frequently. I’d also survey the entire organization (with the help of this new leadership team) and gain a keen understanding of what the various experts feel are the main things that are holding the organization back. Basically, I’d work night and day and many meetings would be taking place.

My first real order of business would be to ensure that the franchise handles the Rule 5 Draft more thoughtfully and effectively. I’d need to bring in many scouts from outside the organization and factor their opinions of players who would be left unprotected. My main hope here would be to avoid giving away another Garrett Whitlock or Trevor Stephan. I’d want the organization to have a much better handle on the players they currently have and I’d actually want to see these players more on the big league team during a season so dovetailing into this first move, I’d begin to systematically unclog the roster.

The first order of business would be to secure Aaron Judge. He’s the face of the franchise and he deserves a fair contract that pays him accordingly. I’d be less concerned about the back end of the deal and more concerned with winning a World Series - also factoring in all the money the franchise has saved by paying Judge what he’s made in his career to date. This is an extreme spend obviously, but one I would view as a “must-make.” The team also doesn’t have a shortstop so no plan would be legitimate that didn’t resoundingly solve that issue for the foreseeable future. More on that in a moment, but firstly and most importantly, I’m an owner who understands that pitching wins championships and folks - I want a darn championship! It’s been 13 years and counting now. This isn’t going to continue, not on my watch! We’re talking about the New York Yankees here, the most storied and successful team in sports history.

Therefore, Brian Cashman would have clear guidance. I’d want a full court press and emphasis on pitching and he would not be choosing the pitchers. I’d tell him which ones to sign and I’d give him my checkbook, with explicit directions to go forth and make it happen.

We’d absolutely be reshaping the starting rotation and besides making Cashman double back, apologize to, and then secure Aaron Judge, the main order of business in the 2023 offseason would be to build a dominating pitching staff - one capable of paving the way to a championship.

Personally I believe the rotation has held the Yankees back in the last 13 seasons and with how competitive the game is now, no area of the team is more important. After a round or two of in-house meetings, we’d identify pitchers we’re just not sold on as being able to win multiple postseason starts. Jameson Taillon, who is a quality starter, would not be tendered. Obviously, Jordan Montgomery was traded away already. The Yankees had a Top 10 rotation in 2022, but obviously, it wasn’t enough if the team didn’t win it all. Change needs to happen.

The Yankees have long been plagued by too many righties in the rotation. This team plays half its games in a ballpark that favors lefties. I got the memo. I understand what a blueprint to success in the Bronx looks like.

Free Agency is, in my opinion, how a team like the Yankees should probably build a rotation. It’s nice to have controllable, young starters but I’d want the organization to be wholly focused on a World Series championship and that means restoring order to the universe. The Yankees have slipped very far from where they need to be over the tenure of the previous owner, Hal Steinbrenner’s watch. I need to jibe this sleek, pinstriped yacht and tack into the wind if that’s what it takes to ensure a ticker-tape parade happens in Manhattan in October.

Clearly, the team needs to be reshaped and the brand demands a commitment. As team owner, I would need to understand and agree to do whatever it took. It’s grown impossible for fans to access the Yankees, with ballgames exclusively being broadcast on all sorts of platforms. This all has to stop and I’m the kind of owner to slam my foot on the brakes and kick whoever I have to off the bus, if that’s what it takes. Many marketing people would be looking for work, after my first hour on the job. Once done, Yankee games would be available exclusively on the Yes Network and/or public television.

Changing gears with that accomplished, philosophically, it’s proven that pitching wins championships and I’m a team owner who understands this. I’d want to massively bolster the Yankees pitching and I’d spend a ton of money to do that. I obviously don’t like having to spend massive amounts of coin, but Hal Steinbrenner left me no other options. The Yankees are between a rock and a hard place and I can’t have that.

Signing Carlos Rodon, who will probably opt out of his deal, would be the first assignment I would hand to Brian Cashman. I’d open the checkbook to encourage a fast signing, because I need a Costco-sized shopping cart to navigate the 2023 free agent starting pitching shopping aisle. I’d want this deal done immediately. Rodon is a very good fit for the Yankees and his left-handedness is crucial for a team that plays 82 games a season in Yankee Stadium. My next sentence needs to be put in bold print…

I’d also go all out for Jacob DeGrom and Chris Sale both! Realizing of course that both are huge injury risks, the backup plan needs to be two fold and contain the names German and Schmidt. This means I’m parting ways with Jameson Taillon, a very effective day in and day out starter and, in a shocking development, I’m moving Luis Severino into the closer's role. I’d also insist on deploying a 6-man rotation, with the obvious goal of limiting innings and keeping people fresh. If it didn’t work, I’d be accountable and the fan base could blame me. The starting rotation would be:

  1. Jacob DeGrom (signed as a free agent)

  2. Garrit Cole

  3. Chris Sale (signed as a free-agent)

  4. Carlos Rodon (signed as a free-agent)

  5. Nestor Cortes Jr (extended)

  6. Frankie Montas (extended)

Focusing so much on the rotation and signing Aaron Judge would deplete much of my financial resources I’m sure. But, there’s still work left to do. I’d also want to revamp the bullpen as much as possible. That would mean a two-phase approach. First, in team meetings we’d decide to move on from Aroldis Chapman, Zack Brittion, Miguel Castro and many others. Roster spots would be opened up and sime payroll would be saved here. I’d encourage Cashman to attempt to trade for Joe Manitply of Arizona and David Bednar of Pittsburgh and if it meant using top prospects (which would be needed for a Bednardeal), I’d sign off.

The bullpen I envision saves money and does require a few trades to shape. Using Sevy as a closer makes sense. Severino could dial it up in short spurts and he’s already proven to be pretty dynamite coming out of a bullpen. He’s also capable of multiple innings as needed and I think with a high-leverage lefty-righty combination of Bednars and Mantiply locks down the 8th and 9th innings for the Yankees.

That leaves Holmes, Loaisiga, Marinaccio, Effross Trivino and Leutge to handle lower leverage roles, where all are probably best suited:

● Closer: Louis Severino

● David Bednars (huge trade, probably would have to part with Dominguez)

● Joe Mantiply (traded a good prospect or two to get him as well)

● Clay Holmes

● Jonathan Loaisiga

● Ron Marinaccio

● Scott Effross

● Lou Trivino

● Lucas Leutge

Positionally, a lot of money was spent in-house, committing to players I’d want to build around. A first step would involve meetings with my advisors to hone the positional plan, but I’d want to see the team move on from Josh Donaldson, Marwin Gonzalez, Gleyber Torres, Aaron Hicks and Kiner-Falefa. What I’d want back is basically prospects because moving them is designed to open roster spots.

The plan really starts with solving the shortstop fiasco that Cashman has let fester for too long. We don’t know if Oswald Peraza is an offensively capable big league player or not. We do know, he’s pretty solid defensively. With Falfa traded, an opportunity exists to add an offensive force and Xander Bogarts, who will be a free agent, just might take a high AAV, shorter term deal. He’d be a great fit and I’d have to be willing to sign him. Too much is invested in this team at this point to not add Bogarts and adding a player like him might put this Yankees team over the top.

With DJ LeMahieu playing mostly third base and a little second base and Gleyber Torres traded for surprising little (he’s actually not worth much these days), Oswald Peraza and Oswaldo Cabrera can provide utility depth for this team and get gradual tastes of playing shortstop on any off-days that Bogarts gets. Meanwhile, the pair can also play some third base and second base. Lot’s of flexibility there but Bogarts is needed as the everyday shortstop and he’s a player who can really hit good pitching. I think he adds a ton to the Yankees lineup.

Extending Luis Trevino is a subtle move that ensures the All-Star catcher continues to be the heart and soul of the team. He’s just too valuable of a player defensively and his impact on games is something I don’t feel a world-class pitching staff that I’ve assembled can live without.

From there, the plan is pretty easy. Rizzo would be extended, Benintendi would be re-upped with and I’d see to it that Carpenter would finish his career in pinstripes as he’s already proven he’s a terrific fit and an handle a bench role because he’s a professional hiter

One last final move would be to target the Cub’s Ian Happ, who becomes the team’s fourth outfielder and he provides some very solid left-handed batsmanship. If he can’t be acquired, (and I think he could be had), then signing Joc Pederson for that 4th outfielder role might make sense.

Here, then, is the rest of my team:

  1. Benintendi LF (re-upped with)

  2. Bogarts SS

  3. Judge RF-CF

  4. Rizzo 1B (extended)

  5. Stanton DH-RF

  6. Cabrera 2B-Utility Player (off limits in any trades)

  7. LeMahieu 3B-2B

  8. Trevino C

  9. Bader CF

Bench: Carpenter (re-upped with on a career-ending deal of 2 years), Higgy, Oswald Peraza, Happ or Pederson.






Bader just might turn out to be a real CFer.

they think that they have LFers on the way with Pereira and Dominguez

they think that they have shortstop s coming with Peraza and (perhaps) Volpe.... with Cabrera backing up ...and Arias to follow

as for 3B ...they're also stocked Donaldson may not hit anymore but he's still got a glove and a fine back-up in DJ..... and Kiner-Falefa is said to play a pretty fair third.

that you would question 1B and catcher must be based on thinking ahead. Rizzo is jus' fine for the nonce and Trevino is a gem no longer hidden as well as under team control for the next couple of years.

if they pay…



good post. good plan.

premium rotation pieces and retaining Judge

might want to steer clear of Bogaerts, though. the team probably doesn't need a bat-first shortstop. if that's the desire Volpe is close to hand.

you've seen Cabrera and liked him. Peraza is widely regarded as a far superior defender at shortstop and ready for prime-time. save the Bogaerts money and spend it on a starter.

and if you want a reserve outfielder with a lefty power bat, try to get one who also pitches.


Trea Turner?



A few more comments. Your rebuild assumes that Bogaerts wants to play here; that Mantiply and Bednars can be acquired; that deGrom wants to play here; and that Sale gets over his chronic injuries. What your plan doesn't address is the problem with the Yankees inability to develop players. I understand that rebuilding a player development system takes time and radical changes to staff but we are right back where we were depending on trades and free agents. I also have a problem with Stanton who is aging and cannot stay on the field. He's a big swing and miss, low contact, high strikeout guy right in the middle of the order.

Cary Greene
Cary Greene

With this sort of question, I think lots of assumptions probably do have to be made. Good points though on your part!

Regarding Stanton, he never really lived up to MVP levels, but when right, he's a fearsome power hitter who can hit any pitcher at any given moment. Of course he has the no trade and the tremendous negative MTV so moving him would be nearly impossible. He was the albatross contract that Cashman took on and really, Stanton will go a long ways towards defining Cashman's legacy.



Cary: So in your model, the owner basically becomes the GM and Chief Operating Officer. Then why do we need Cashman? He would be reduced to a high-level clerk. In addition, you did not address the manager and coaching positions. You want to keep Boone and his coaches? If you are gutting the club and rebuilding, how can we keep Boone who has shown he lacks the skills and experience to manage men?


Cary Greene
Cary Greene

Keeping Aaron Boone or not keeping him would be up to the general manager, and yes, I don't believe Cashman has been given free rein or ability to spend on key players such as Francisco Lindor, or Mookie Betts ..etc so when we really look at the Yankees roster it's the same old problems every season. The Yankees have no real left fielder. They have no center fielder, there's no shortstop, who's playing third base? Who's playing first base? Do we have a catcher? On and on it goes.

Literally none of that has anything to do with Aaron Boone. Not to mention? Who is Aaron Boone's bench coach? If he's a bad in-game manager in a poor pitching staff…

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