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Perspectives: The Questions To Ask (And the Answers)

by Paul Semendinger

July 27, 2021


The Yankees have not had a great season.

I believe it’s time that the organization asks itself some hard questions.

(And, because I’m kind, I also have provided the answers.)

Are the 2021 Yankees World Series contenders? No. Even if they sneak into the playoffs where anything, of course, can happen, it is unlikely that this team will win three playoff series.

Is it worth investing in the 2021 Yankees? No. It’s time to look forward and start to plan for 2022 and beyond. This club, as currently constructed, is not built for success going forward. The window was now, these last four years. They didn’t get it done. The window on this core has closed.

If the story of the 2021 Yankees is indeed over, shouldn’t they start preparing now, rather than in the off-season, for 2022 and beyond? Yes. To stand pat and wait address the team’s needs is foolish. Time wasted is time wasted. The Yankees could get a jump on next year, by seriously planning for it right now.

Is it likely that any of these players, all 31-years-old, or older, will be part of the next Yankees competitive era: D.J. LeMahieu (32), Brett Gardner (37), Giancarlo Stanton (31), Ryan LeMarre (32), Zack Britton (33), Aroldis Chapman (33), Lucas Luetge (34), Justin Wilson (33)? No.

What should be done with those players? The Yankees should find a way to maximize the team’s future by seeking deals for any or all of them.

What should be done with Aaron Judge? The Yankees have a huge decision here. I believe Aaron Judge is going to want a superstar contract. And why not? He deserves it. But, he has never played a full season completely healthy. And he’ll be 30 next year. Whoever signs Judge will be paying for his decline. If the Yankees are going to use Judge’s contract as the reason (or excuse) not to get other necessary pieces, then they should trade him for talent they can use. The Yankees cannot win if they allow the monster contracts they sign with certain players to restrict their spending in other areas. If Aaron Judge’s contract weighs the team down, he’ll be to the Yankees of the 2020s what A-Rod was to the Texas Rangers – a luxury they can’t afford who stands in the way of winning. This is on the Yankees. Keep the superstar and keep moving forward in building a winner or let him go. They cannot keep Aaron Judge and try to play the financially prudent game. The two are mutually exclusive if the object is to have a team that can win the World Series.

Did the Yankees strategy of loading up on right-handed power hitters bring them a championship? No, it did not.

Is it likely that it ever will? No. Not at all. This was readily apparent from the start. The Yankees have never won without high quality left-handed bats in the lineup. This is something that has been true since a certain Babe Ruth first wore pinstripes.

Did the Yankees’ strategy of not having high-quality left-handed starting pitchers work well? No. Not at all. This was readily apparent from the start. The Yankees have never won without high quality left-handed starting pitching. This is something that has been true since Herb Pennock first wore pinstripes.

The last time the Yankees sold at the deadline, they acquired a host of high-end young talent. Did those players pan out? No. None of the players acquired back in 2016 have fulfilled their tremendous promise.

Have the other young stars, the ones from within the organization or acquired in other deals blossomed? No, not really. Outside of Aaron Judge, they have all fallen short of their promise.

What does that say about the organization? It seems to indicate that there is something wrong with the player development end and that certain organizational philosophies have not worked as well as they should have.

What does that say? It is time for some changes – radical, big, organizational changes…

Aaron Boone was hired as manager with no coaching or managerial experience for the 2018 season. Have the Yankees grown and performed better or regressed during his tenure? They most certainly have regressed. They are further away from contending now than when Aaron Boone was hired. The Yankees have gone backwards.

Does it seem like Aaron Boone is the manager who can take the Yankees to their next championship? No.

If a change needs to be made, when should that change be made? The sooner the better. Why wait until November for a decision that seems clear in July?

Many years ago, Brian Cashman asked to be the person who had the ultimate voice in all player moves. He wanted full responsibility. Since that happened, have the Yankees won any World Series? No.

What does that say? It says that the team as designed by the General Manager has not fulfilled its mission.

Were the Yankees close to winning it all during Brian Cashman’s tenure? Yes.

Are they closer today than they were two years ago, or four years ago? No and no.

Who hired the manager and built the roster that has under performed these last few years? Brian Cashman

What does that say? It seems the philosophy Brian Cashman has brought has not worked. Brian Cashman has to own this. This is his club. At this point, Brian Cashman needs a new approach, there needs to be other decision makers with power involved in the process, or it is time for a change at the General Manager position as well.

If a change needs to be made, when should that change be made? The sooner the better so the new decision makers, or new organizational approach, can get to work now, rather than in November. Time wasted is time wasted.

Has he Yankees’ strategy of being overly budget conscious won them any World Series? No.

The last time the Yankees won the World Series, what was different? They spent and spent and spent to bring a winner to New York.

What does this say? It is time to spend again. The Yankees’ big advantage is their gigantic revenue stream and deep deep pockets. By not using this obvious advantage, the Yankees only hurt themselves. The Yankees have the financial wherewithal as the sports’ most lucrative franchise to never have to worry about budgets. By not using the advantage they have, the Yankees have put themselves at a huge disadvantage. This makes no sense. The Yankees are not the Kansas City Royals and should not operate as if they are the Kansas City Royals. This is a self-inflicted wound that has hurt the franchise and has greatly upset the fan base. The fans were promised better. As the Yankees stay budget conscious and stand under the luxury cap, they still charge their fans some of the highest prices in the game. Both cannot continue.

Are the Yankees heading into a period of being a second-division clubs? No. It doesn’t have to be. At all. With better financial management by the Yankees using their great financial advantage as an tool, with better decision-making regarding players, with better player development, and with a field manager who has experience in winning and bringing out the best in his players, the Yankees could be competitive as early as next year. It would take a huge organizational change in philosophy for this to happen. The question is if the Yankees have the courage to do this. If they do not, do not count on any championship flags any time soon.

So what needs to be done? The Yankees have to admit their mistakes by fixing them, and getting to work now, not in November (or later) to fix those mistakes and address all of the many issues this current team has.

What if the Yankees hold firm with their current approach? They won’t be winning any championships any time soon.


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