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Yankees 25 best moves of the last 25 years
4 months ago  ::  Jan 20, 2022 - 8:26PM #1
Giancarlo
Posts: 804

As Pinstripe Alley wraps up its series on the Yankees’ 27 championship teams this week, Major League Baseball shows few signs of ending its lockout of the players anytime soon. It’s disappointing, but thankfully, our chosen ballclub has an extremely rich history to explore as we pass the time amid our other articles.


So today, PSA will begin a new series detailing the Yankees’ 25 smartest moves of the past 25 years (nearly all of current GM Brian Cashman’s tenure). The degree of intelligence behind each transaction is quite subjective, so I enlisted 12 other staff members to help out in the selection process. Note that none of these nominees are draft selections like Aaron Judge, or amateur international free agent signings like Luis Severino because I had to draw a line somewhere, and with players that young, the odds of a “smart” move going bust are even higher. Also, we will not be ranking the 25 moves, as that is an even more arbitrary endeavor, and it was difficult enough for us to narrow down the chosen transactions from a list of 40 nominees.


Instead, we’ll simply be going in chronological order with the 25 moves that were chosen the most among the staff who participated. There were some tough omissions, but then again, 25 years is a lot of time for plenty of well-executed transactions to be pulled off. For example, I have a particular fondness for both the out-of-nowhere Bartolo Colón signing in 2011 and Cashman acquiring steady starter Brandon McCarthy in July 2014 for Vidal Nuño, but neither addition made the cut.


We won’t spoil which 25 transactions made our list just yet, but as each one is revealed, links will be added to this master post. We’ll begin today with Jon discussing the landmark signing that brought Orlando “El Duque” Hernández to the Bronx from Cuba in 1998. Look for each subsequent post to come every weekday!


3/23/1998 - Orlando Hernández signed
6/29/2000 - The David Justice trade
12/7/2000 - Mike Mussina signed
TBD - January 20th
TBD - January 21st
TBD - January 24th
TBD - January 25th
TBD - January 26th
TBD - January 27th
TBD - January 28th
TBD - January 31st
TBD - February 1st
TBD - February 2nd
TBD - February 3rd
TBD - February 4th
TBD - February 7th
TBD - February 8th
TBD - February 9th
TBD - February 10th
TBD - February 11th
TBD - February 14th
TBD - February 15th
TBD - February 16th
TBD - February 17th
TBD - February 18th

4 months ago  ::  Jan 20, 2022 - 8:29PM #2
Giancarlo
Posts: 804

If they're going in chronological order they're already leaving out the Clemens for Wells trade.


But this list should counter all the "Cashman is terrible" narrative folks out there.


If he's so bad, bring up 25 moves that are as bad as these will be good.  They will be adding a move each day until they fill out all 25.


1 month in to his tenure and he signs El Duque, one of the most clutch post season pitchers in history.


Justice was also a great move, and Moose went on to the HOF.

4 months ago  ::  Jan 31, 2022 - 8:57PM #3
JudgeandYankees
Posts: 577

Jan 20, 2022 -- 8:29PM, Giancarlo wrote:


If they're going in chronological order they're already leaving out the Clemens for Wells trade.


But this list should counter all the "Cashman is terrible" narrative folks out there.


If he's so bad, bring up 25 moves that are as bad as these will be good.  They will be adding a move each day until they fill out all 25.


1 month in to his tenure and he signs El Duque, one of the most clutch post season pitchers in history.


Justice was also a great move, and Moose went on to the HOF.




When he had an owner like the late George Steinbrenner who gave him pretty much an unlimited payroll it's really not that impressive.  How many championships have the Yankees won or how many times have they made it to the world series since he passed away?

4 months ago  ::  Feb 01, 2022 - 11:28AM #4
Giancarlo
Posts: 804

Jan 31, 2022 -- 8:57PM, JudgeandYankees wrote:


Jan 20, 2022 -- 8:29PM, Giancarlo wrote:


If they're going in chronological order they're already leaving out the Clemens for Wells trade.


But this list should counter all the "Cashman is terrible" narrative folks out there.


If he's so bad, bring up 25 moves that are as bad as these will be good.  They will be adding a move each day until they fill out all 25.


1 month in to his tenure and he signs El Duque, one of the most clutch post season pitchers in history.


Justice was also a great move, and Moose went on to the HOF.




When he had an owner like the late George Steinbrenner who gave him pretty much an unlimited payroll it's really not that impressive.  How many championships have the Yankees won or how many times have they made it to the world series since he passed away?




I think it's easy to also make bad signings and trades, even with a high payroll.


How many times have they missed the playoffs?   How many other teams can compare with that?


And at this point, it's not really all about cash, but also the penalties that come along with the luxury tax:


Why luxury tax negotiations are pertinent to Yankees fans (audacy.com)


Should they be willing to weaken their drafts with lower picks and less total pool money to sign the guys they do draft?   Should they be willing to take hits to the pool of money they get to sign international prospects as well?   I know they'd also hate to see luxury tax penalty money ending up in the hands of teams like the Rays.   It's a different world right now (at least pending the new CBA, maybe that will change things).   


The more I look at it, I don't think Hal is being cheap, but rather looking to keep the other tax penalties under control.   In the long term that may actually lead to stronger teams via drafts and signing top international prospects like Rod-A.

4 months ago  ::  Feb 01, 2022 - 5:16PM #5
JudgeandYankees
Posts: 577

Feb 1, 2022 -- 11:28AM, Giancarlo wrote:


Jan 31, 2022 -- 8:57PM, JudgeandYankees wrote:


Jan 20, 2022 -- 8:29PM, Giancarlo wrote:


If they're going in chronological order they're already leaving out the Clemens for Wells trade.


But this list should counter all the "Cashman is terrible" narrative folks out there.


If he's so bad, bring up 25 moves that are as bad as these will be good.  They will be adding a move each day until they fill out all 25.


1 month in to his tenure and he signs El Duque, one of the most clutch post season pitchers in history.


Justice was also a great move, and Moose went on to the HOF.




When he had an owner like the late George Steinbrenner who gave him pretty much an unlimited payroll it's really not that impressive.  How many championships have the Yankees won or how many times have they made it to the world series since he passed away?




I think it's easy to also make bad signings and trades, even with a high payroll.


How many times have they missed the playoffs?   How many other teams can compare with that?


And at this point, it's not really all about cash, but also the penalties that come along with the luxury tax:


Why luxury tax negotiations are pertinent to Yankees fans (audacy.com)


Should they be willing to weaken their drafts with lower picks and less total pool money to sign the guys they do draft?   Should they be willing to take hits to the pool of money they get to sign international prospects as well?   I know they'd also hate to see luxury tax penalty money ending up in the hands of teams like the Rays.   It's a different world right now (at least pending the new CBA, maybe that will change things).   


The more I look at it, I don't think Hal is being cheap, but rather looking to keep the other tax penalties under control.   In the long term that may actually lead to stronger teams via drafts and signing top international prospects like Rod-A.





I don't think signing the top free agents constantly makes Cashman a great gm.  Our last championship we won because we signed CC, AJ and Tex.  Since then the Yankees have done squat.


I'm not even blaming Hal, the Yankees still spend a lot of money but it's not as much as his father and he's not as passionate about being the best team on paper.  It's up to Cashman to work with what's he's got and so far the Yankees have been a disappointing since he's had a greater rein on things.

4 months ago  ::  Feb 01, 2022 - 9:49PM #6
Paterson
Posts: 7,637

Feb 1, 2022 -- 5:16PM, JudgeandYankees wrote:


Feb 1, 2022 -- 11:28AM, Giancarlo wrote:


Jan 31, 2022 -- 8:57PM, JudgeandYankees wrote:


Jan 20, 2022 -- 8:29PM, Giancarlo wrote:


If they're going in chronological order they're already leaving out the Clemens for Wells trade.


But this list should counter all the "Cashman is terrible" narrative folks out there.


If he's so bad, bring up 25 moves that are as bad as these will be good.  They will be adding a move each day until they fill out all 25.


1 month in to his tenure and he signs El Duque, one of the most clutch post season pitchers in history.


Justice was also a great move, and Moose went on to the HOF.




When he had an owner like the late George Steinbrenner who gave him pretty much an unlimited payroll it's really not that impressive.  How many championships have the Yankees won or how many times have they made it to the world series since he passed away?




I think it's easy to also make bad signings and trades, even with a high payroll.


How many times have they missed the playoffs?   How many other teams can compare with that?


And at this point, it's not really all about cash, but also the penalties that come along with the luxury tax:


Why luxury tax negotiations are pertinent to Yankees fans (audacy.com)


Should they be willing to weaken their drafts with lower picks and less total pool money to sign the guys they do draft?   Should they be willing to take hits to the pool of money they get to sign international prospects as well?   I know they'd also hate to see luxury tax penalty money ending up in the hands of teams like the Rays.   It's a different world right now (at least pending the new CBA, maybe that will change things).   


The more I look at it, I don't think Hal is being cheap, but rather looking to keep the other tax penalties under control.   In the long term that may actually lead to stronger teams via drafts and signing top international prospects like Rod-A.





I don't think signing the top free agents constantly makes Cashman a great gm.  Our last championship we won because we signed CC, AJ and Tex.  Since then the Yankees have done squat.


I'm not even blaming Hal, the Yankees still spend a lot of money but it's not as much as his father and he's not as passionate about being the best team on paper.  It's up to Cashman to work with what's he's got and so far the Yankees have been a disappointing since he's had a greater rein on things.




    While I think the Yankees have been better than "squat" since their last World Series win, in general I agree with you. It should be recalled that Cashman got full authority as GM only in the last decade or so. As recently as January of 2011 Rafael Soriano got a three year deal over his objections. Looking at Yankee history over the past quarter century, things worked better when he had less control. 

4 months ago  ::  Feb 01, 2022 - 11:26PM #7
JudgeandYankees
Posts: 577

Feb 1, 2022 -- 9:49PM, Paterson wrote:


Feb 1, 2022 -- 5:16PM, JudgeandYankees wrote:


Feb 1, 2022 -- 11:28AM, Giancarlo wrote:


Jan 31, 2022 -- 8:57PM, JudgeandYankees wrote:


Jan 20, 2022 -- 8:29PM, Giancarlo wrote:


If they're going in chronological order they're already leaving out the Clemens for Wells trade.


But this list should counter all the "Cashman is terrible" narrative folks out there.


If he's so bad, bring up 25 moves that are as bad as these will be good.  They will be adding a move each day until they fill out all 25.


1 month in to his tenure and he signs El Duque, one of the most clutch post season pitchers in history.


Justice was also a great move, and Moose went on to the HOF.




When he had an owner like the late George Steinbrenner who gave him pretty much an unlimited payroll it's really not that impressive.  How many championships have the Yankees won or how many times have they made it to the world series since he passed away?




I think it's easy to also make bad signings and trades, even with a high payroll.


How many times have they missed the playoffs?   How many other teams can compare with that?


And at this point, it's not really all about cash, but also the penalties that come along with the luxury tax:


Why luxury tax negotiations are pertinent to Yankees fans (audacy.com)


Should they be willing to weaken their drafts with lower picks and less total pool money to sign the guys they do draft?   Should they be willing to take hits to the pool of money they get to sign international prospects as well?   I know they'd also hate to see luxury tax penalty money ending up in the hands of teams like the Rays.   It's a different world right now (at least pending the new CBA, maybe that will change things).   


The more I look at it, I don't think Hal is being cheap, but rather looking to keep the other tax penalties under control.   In the long term that may actually lead to stronger teams via drafts and signing top international prospects like Rod-A.





I don't think signing the top free agents constantly makes Cashman a great gm.  Our last championship we won because we signed CC, AJ and Tex.  Since then the Yankees have done squat.


I'm not even blaming Hal, the Yankees still spend a lot of money but it's not as much as his father and he's not as passionate about being the best team on paper.  It's up to Cashman to work with what's he's got and so far the Yankees have been a disappointing since he's had a greater rein on things.




    While I think the Yankees have been better than "squat" since their last World Series win, in general I agree with you. It should be recalled that Cashman got full authority as GM only in the last decade or so. As recently as January of 2011 Rafael Soriano got a three year deal over his objections. Looking at Yankee history over the past quarter century, things worked better when he had less control. 




They haven't been to the World Series since 2009, this is the Yankees we don't go around bragging about being division champs so yeah they haven't done squat since then.

4 months ago  ::  Feb 04, 2022 - 9:13AM #8
Giancarlo
Posts: 804
4 months ago  ::  Feb 07, 2022 - 10:07AM #9
bruner4329
Posts: 4,482

Feb 1, 2022 -- 11:26PM, JudgeandYankees wrote:


Feb 1, 2022 -- 9:49PM, Paterson wrote:


Feb 1, 2022 -- 5:16PM, JudgeandYankees wrote:


Feb 1, 2022 -- 11:28AM, Giancarlo wrote:


Jan 31, 2022 -- 8:57PM, JudgeandYankees wrote:


Jan 20, 2022 -- 8:29PM, Giancarlo wrote:


If they're going in chronological order they're already leaving out the Clemens for Wells trade.


But this list should counter all the "Cashman is terrible" narrative folks out there.


If he's so bad, bring up 25 moves that are as bad as these will be good.  They will be adding a move each day until they fill out all 25.


1 month in to his tenure and he signs El Duque, one of the most clutch post season pitchers in history.


Justice was also a great move, and Moose went on to the HOF.




When he had an owner like the late George Steinbrenner who gave him pretty much an unlimited payroll it's really not that impressive.  How many championships have the Yankees won or how many times have they made it to the world series since he passed away?




I think it's easy to also make bad signings and trades, even with a high payroll.


How many times have they missed the playoffs?   How many other teams can compare with that?


And at this point, it's not really all about cash, but also the penalties that come along with the luxury tax:


Why luxury tax negotiations are pertinent to Yankees fans (audacy.com)


Should they be willing to weaken their drafts with lower picks and less total pool money to sign the guys they do draft?   Should they be willing to take hits to the pool of money they get to sign international prospects as well?   I know they'd also hate to see luxury tax penalty money ending up in the hands of teams like the Rays.   It's a different world right now (at least pending the new CBA, maybe that will change things).   


The more I look at it, I don't think Hal is being cheap, but rather looking to keep the other tax penalties under control.   In the long term that may actually lead to stronger teams via drafts and signing top international prospects like Rod-A.





I don't think signing the top free agents constantly makes Cashman a great gm.  Our last championship we won because we signed CC, AJ and Tex.  Since then the Yankees have done squat.


I'm not even blaming Hal, the Yankees still spend a lot of money but it's not as much as his father and he's not as passionate about being the best team on paper.  It's up to Cashman to work with what's he's got and so far the Yankees have been a disappointing since he's had a greater rein on things.




    While I think the Yankees have been better than "squat" since their last World Series win, in general I agree with you. It should be recalled that Cashman got full authority as GM only in the last decade or so. As recently as January of 2011 Rafael Soriano got a three year deal over his objections. Looking at Yankee history over the past quarter century, things worked better when he had less control. 




They haven't been to the World Series since 2009, this is the Yankees we don't go around bragging about being division champs so yeah they haven't done squat since then.




Its really simple. Starting pitching depth, good bullpen and balanced lineup with timely hitting and grinding at bats.


It started when Cashman started breaking the mold. With starting pitching we never seemed to have a solid 1-3 after 2012. It was always CC and thenKuroda and then Tanaka along with  a bunch of projects and guys coming off of down years. Then Severino and now Cole. While the bullpen has remained strong it gets over worked because our starters are limited in distance. Finally when Cashman started bringing in guys like Steven Drew and trading for a guy like Hicks and giving him a 7 year contract things started falling off a bit. You look at this lineup and there are too many give away at bats and often seems impossible to put together a couple of hits in a row. Who are the grinders we have right now. DJ and Judge and maybe Rizzo who may not be back, who else. If guys like Torres, Stanton and Voit get behind in the count you can bet they will chase the ball in the dirt. And forget Gallo he is a K machine. Sanchez pretty similar as well. When over 50% of your lineup struggles to make consistent contact that is a huge problem.

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