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Looking Ahead to the 2021 Yankees – My Approach To The Off-Season, Part 1

by Paul Semendinger 10/16/20


I usually call these off-season articles where I share my plan for building the next year’s Yankees, “If I Was The GM.” This year, though, I believe the Yankees have to make a decision regarding Brian Cashman and his role with the team, so I guess this year I’ll have to write these as if I was the hands-on owner of the team.

Whatever my role, if I ran the Yankees, the following would be my approach to the off-season.

I believe there are some big issues that will frame the Yankees’ off-season. I’ll outline these specific ideas today and then go into the specific in my follow-up articles.

There are six areas of focus the Yankees need to look at. Let’s examine each in order:

Step 1 – Offer a Vote of Confidence in my General Manger, Brian Cashman

Brian Cashman is probably the best GM in the business, but there are a few things I would have to address with him. These are as follows:

A) I would stress that the goal for the 2021 Yankees is to win. The Yankees have been a very good team for most years of this century, but it is a century that has not had many World Series appearances or World Championships. That needs to change. Brian Cashman often plays the long game. He thinks long-term, which is great and which I appreciate, but there also needs to be a sense of a bit more urgency. As the owner, I know that my fanbase is getting tired of waiting for the next World Series. Brian Cashman has been preaching patience for close to a decade. The fans have been patient. I need my general manager to become more aggressive in the trade market. When needs arise, I will need him to find a way to get the necessary talent to help the team get over the hump. I don’t want to hear, any longer, that the costs were too high for Player X and, at the same time see other teams wheeling and dealing. It’s not longer a long game. If the Yankees had acquired pitching at the trade deadline, I remind my general manager, they might have gotten past the Tampa Bay Rays. In some senses, the Yankees were just one pitcher away.

B) I would also change the philosophy that the general manager and the analytics team should be part of the game strategy. I would stress that the general manager and the analytics teams are not the field manager. Going forward, we will not be having any more organizational decisions regarding in-game decision making. Aaron Boone will be entering his fourth season as manager. If he doesn’t know how to manage by now, I suggest that he be fired. But, believe it or not, I think he does know how to manage, so my directive is to leave him alone to figure out how to best use the players on his roster. The analytics team can, of course, advise, but going forward they are out of the day-to-day game strategy decisions. Going forward Aaron Boone makes the lineups, figures out the pitching match-ups, and makes the calls to the bullpen as he deems appropriate and necessary at the time and in the moment. All of the in-game decisions belong to Boone. Period.

Step 2 – Offer a Vote of (somewhat) Confidence in my Field Manager, Aaron Boone

We brought Aaron Boone in as the manager knowing there was a learning curve and there would be bumps along the way. That being said, 2021 will now be his fourth season. It’s time for him to establish himself as the manager. I tell Mr. Boone that the team is his to run as he sees fit. Brian Cashman will build the team, with Boone’s input, of course, but the day-to-day decision making and the in-game decision making are now Boone’s entirely. By now he should know how to do this.

I also bring Aaron Boone back because the 2021 Yankees might have many new players. I am promising an active off-season. There will be changes to the roster. With the amount of change that might be coming, I’d like to have stability in leadership. The 2021 Yankees will be Aaron Boone’s to lead, but in this, as I give my support, I also give Mr. Boone a few directives. There are a few things that must happen this year. These are as follows:

A) Fundamentals must be a focus in Spring Training and throughout the year. I’m tired of seeing sloppy play. When it counts, the Yankees routinely get beat by teams that play a better brand of fundamental baseball.

B) The team needs more hustle and energy. These are unquantifiable factors that are often overrated or confused with success. But, that being said, the Yankees, at times, lack energy. The Yankees routinely get beat by teams that exhibit more energy. I do not want to see the Yankees out-energized in 2021.

C) I insist that Aaron Boone to search far and wide for a brilliant longtime baseball mind, a person with a wealth of knowledge and experience, to be his bench coach. Boone needs a Don Zimmer type sitting next to him in the dugout. He needs the sage voice who offers perspectives and also challenges his thinking to offer necessary perspectives that become the little things that often make a difference. I believe that a great bench coach, a man who knows the game, would help Aaron Boone immensely. That voice, I state, should also come from outside the current organization. The teams needs from fresh eyes to make critical and essential decisions.

Step 3 – Make a decision of Free Agent D.J. LeMahieu

This is the first, and most critical decision the Yankees must address to begin the off-season. All of my other moves hinge on the decision we make with D.J. LeMahieu.

As far as LeMahieu goes, we are going to need a quick decision. He just finished his age-32 season. Second basemen don’t always age well. I would prefer a 3 years/$60m deal for him. I might go four years, but five is completely out of the question. If LeMahieu wants five years, I let him walk.

All of the decision we make this off-season hinge off whether of not LeMahieu comes back. If he signs again with the Yankees, he becomes the second baseman for the next amount of years. But if he does not sign with the Yankees, I make Gleyber Torres my second baseman and seek ways to improve the defense at shortstop.

I will give D.J. LeMahieu a fair offer, but I will insist he decide quickly as I cannot let this decision hold-up the rest of my off-season.

Step 4 – Recognize that the lineup has too many right-handed hitters and that this must change.

As part of this decision-making, I would recognize that of these players: Gleyber Torres, Clint Frazier, Giancarlo Stanton, Aaron Judge, Gary Sanchez, Miguel Andujar, Gio Urshela, and Luke Voit, at least some, probably two, have to be traded – as much as that hurts. If LeMahieu signs, that adds another right-handed batter to the mix. This lack of balance continues to hurt the Yankees. It must change.

I also know that the easiest to deal guys (at this point Frazier and Andujar) are not the ones who are going to significantly change this team’s dynamic. I know that I am going to have to trade some players that have been core pieces over the last few years.

Along with this, I know that I’ll need to acquire a quality respected left-handed hitter who can occasionally start and also come off the bench in a big spot.

Step 5 – Along with Step 4, but not necessarily part of Step 4, is the decision we must make regarding Gary Sanchez.

At this point, Gary Sanchez might just be too much of a distraction and a lightning rod. I may need to free-up my manager to get rid of the constant questions about him. This is a narrative that hasn’t changed since Aaron Boone took over the team – even before. I know that some believe that it was Sanchez who cost the previous manager, Joe Girardi, his job. Gary Sanchez has had a long leash. His performance has not improved, and he seems to be regressing each year. For the team’s sake, and for Sanchez’s sake, we have to look critically as his role on this team.

Step 6 – Get two top-of-the-line starting pitchers.

As the owner, I have to be willing to pay the costs necessary to vastly improve the starting rotation. I have the salaries of Masahiro Tanaka, James Paxton, and J.A. Happ all coming off the books. I have to be willing to use all of that money, and maybe more, to bring in two big arms to solidify the rotation to get the team to the playoffs, but also then to compete with the best teams and the best rotations in the playoffs. I cannot ask Gerrit Cole to do this alone. That’s not fair to him, because it would be impossible, but since I invested, big time, in Cole, from a business standpoint, I want to treat that investment carefully and not burn him out. He cannot be expected to pitch and win two (or three) games in each post season series.

To get the necessary pitching it will probably involve moving some of the players discussed in Step 4 above.


And that is where I would begin my off-season planning. In sum:

Brian Cashman remains General Manager, but I ask him to feel a bit more urgency and to leave the game strategy to the field manager.

Aaron Boone stays, but I ask him to stress fundamentals and team energy while leaving all of the on-field and in-game decisions to him. But, I also stress that he needs a veteran bench coach at his side.

I seek to sign or move on from D.J. LeMahieu quickly.

I recognize that some popular or high upside Yankees players will have to be traded to give the lineup needed (and essential) balance.

I find and acquire two top-of-the-rotation starters.


Next in the series, I’ll play GM and make the moves necessary to build the new and improved 2021 Yankees…


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