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Should the Yankees be Buyers or Sellers?

Should the Yankees be Buyers or Sellers at the 2023 MLB Trade Deadline?

July Thoughts

by Cary Greene

July 13, 2023


It’s time for changes in the Bronx. Big changes, not so much related to personnel, but more so - it’s time to change the way the Yankees operate and the 2023 MLB Trade Deadline is a perfect opportunity to address some of the problems.

It’s understandable that due to the Yankees having MLB’s second highest payroll, Brian Cashman will be in his annual “World Series or Bust” mode approaching the August, 1st Deadline. However, further depleting what is already a greatly weakened farm system - one that MLB.COM ranked 13th coming into this season - is a bad idea for a number of reasons.

Certainly the first concern with scuttling the system in order to plug some of the many holes that this year’s Yankees ball club has is that the Yankees are and have been for several seasons now, engaged in a partial youth movement. While many of the prospects the Yankees are dreaming on may still be toiling in Double-A, there is a chance some of them might be able to help as soon as next season - so why pull the plug on this endeavor in what amounts to the 10th or eleventh hour?

Another main concern has to be that there is a significant amount of money coming off the books this coming offseason. While it’s true that Yankees owner Hal Steinbrenner will have to pay a $33 million CBT penalty after this season due to having the second highest payroll in baseball, the Yankees will have a small window of opportunity to try and reset the CBT.

While the 2024 CBT adjusts to $237 million, the Yankees payroll shrinks to only $196.6 million to kick off the offseason - which leaves roughly $40.3 million to work with next offseason to try and build a championship caliber team.

With all of this in mind, it may behoove Brain Cashman to attempt an all-in plan to win a title in 2024, while doing the best he can to find some younger, controllable type players that if acquired, could be retained and used towards a future championship push - opposed to continuing to operate with a strategy that requires the Yankees to cough up prospects who will help another team at a later date while yielding only a stopgap player on an expiring contract.

Players like Andrew Benintendi for example, who only have a half a season of team control left on their contracts, are of little value to a team with the Yankees particular circumstances. Right now, it’s time for the Yankees to execute a plan that includes a vision beyond just a one-time “playoffs or bust” push. A strategy like this would dramatically depart from many of Cashman’s usual “non-committal” Andrew Heaney and the aforementioned Benintendi type deals.

Additionally, the Yankees need to scout their own internal talent better and stop giving away players who would have been very useful to fill in future rosters. Players like Thairo Estrada and Ezequiel Duran, Trevor Stephan, Garrett Whitlock and J.P. Sears, just to name a few, could have really helped the Yankees field a vastly better roster not only over the past few seasons, but they each could have yielded valuable dividends going forward into the chapters Hal Steinbrenner has yet to pen in his novel, currently entitled, “Good Enough.”

Let’s face it folks, the Yankees don’t have a ton of trade chips left at this point, at least not ones they can really afford to flush away for stopgap solutions. It’s time to get real. It’s time to come up with an actual plan for the future and there is no doubt, a combination of internal prospects will be needed to help fill in areas on the roster that free agent dollars alone cannot solve.

With that in mind, a better offseason plan should be executed after this season’s final pitch is thrown. The Yankees still have a chance to win a World Series. Carlos Rodon could emerge as a stopper and the Aaron Judge may be able to make his way back and carry the Yankees to a championship. Who knows, perhaps a few sparkplugs like Luke Voit or Mike Tauchman might help the Yankees in key areas and they might not cost as much as people might think. Granted, the chances of obtaining Juan Soto or Shohei Ohtani at a reasonable cost at this year’s deadline are pretty minimal. A better strategy that may make more sense at this year’s Trade Deadline might just be to think about the future.

This offseason, the Yankees will have the ability to sign a few key players. Any pieces they acquire this season, could be added to those pieces and that’s precisely the strategy I think Brian Cashman should take, starting with any trades he makes at the upcoming Deadline.



Jul 14, 2023

An awful lot of things will have to happen for this 2023 rendition of the Yankees to become World Series Champions. I am hopeful but realistically I think they are toast. Cashman has a tough job ahead of him. Without a healthy and productive Judge the season I feel is lost. I don’t see DJ rebounding, Donaldson needs to go. Stanton and Rizzo are on the wrong side of the hill. German and Gleybar could be dealt for some promising youngsters . I don’t think the Yankees have enough to land a Soto (if he became available) or Ohtani ( I really don’t think he wants to play here.) so I feel they ought to give the youngsters they hav…

Cary Greene
Cary Greene
Jul 15, 2023
Replying to

I love your take POPS! Well said!


Cary Greene
Cary Greene
Jul 14, 2023

Hint: Cashman should either get VERY BUSY on both sides of the ball, or he should probably look towards 2024 and THAT my friends, is using history to teach us about both the present and the future. I believe the deck is most likely stacked AGAINST the 2023 Yankees, as constructed. (and I've only ever been truly proven wrong about my World Series sniff test three times. Truly really, only one team has ever proven me wrong and the margin of proof was VERY THIN.


Cary Greene
Cary Greene
Jul 14, 2023

Coincidentally, the 1978 Yankees posted a regular season 105 OPS+ and had a regular season 115 ERA+. Fastforward to right now, the Yankees have a 96 OPS+ and a 111 ERA+. Are they that far off the pace of what past World Series winners have averaged? This is the ultimate trivia question. I bet no one can figure the answers out - so I challenge all of you.

  1. Who can tell us what the average regular season ERA+ and OPS+ is for World Series champions of the past?

  2. How many times in history has a World Series champion EVER averaged below an ____ ERA+ during the regular season?

  3. Is Regular Season ERA+ or OPS+ a better tool to predict a…


Cary Greene
Cary Greene
Jul 14, 2023

The grim reality is, if the Yankees fail to win a World Series this season. Yes. Hal will be tied for the all time franchise streak of no titles. One more season of failure, and he'll be in a class by himself. By Yankees franchise standards - he'll be the biggest failure ever, in franchise history. go Hal! Stick with Cashman and Boone buddy! They know what they're doing baby! Thay got you!


Cary Greene
Cary Greene
Jul 14, 2023

1978, Bucky Dent & the Bronx Bombers defeated the Dodgers in six games. Ron Guidry, Tommy John, Reggie Jackson...those were the days. I was in 8th grade at the time. My pop let me stay up late to watch all of the late games. Wowww. RIP Pop! I love you!

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