How missteps by Yankees ownership, Brian Cashman have led to New York's shocking decline since 2017

How missteps by Yankees ownership, Brian Cashman have led to New York's shocking decline since 2017

At 60-58, the New York Yankees are not only in danger of missing the postseason for the first time since 2016, they are in danger of finishing with a losing record for the first time in three decades. The Yankees have not had a losing season since going 76-86 in 1992. Their 30-year winning-season streak is the second longest in MLB history behind a 39-year streak by the 1926-64 Yankees.

"Obviously, we need victories," manager Aaron Boone said after Sunday's crushing walk-off loss to the Miami Marlins (video). "... We got to rack up wins. As tough as this one is to swallow, you've got to move on from it."

The Yankees are 6-10 since Aaron Judge returned from his toe injury (he is playing on a torn ligament) and 24-33 in their last 57 games. Dating back to last season, they are 84-78 in their last 162 games, postseason included. New York's struggles are no longer a small sample size. They've been a mediocre team for a full year now and worse than mediocre lately.

The roster lacks impact players beyond Judge and Gerrit Cole. Big-name veterans like Giancarlo Stanton and DJ LeMahieu have underperformed, expected difference-makers Carlos Rodón and Luis Severino have been hurt and ineffective, and too many at-bats are going to the Billy McKinneys and Ben Rortvedts of the world. Touted rookie shortstop Anthony Volpe has looked better than the numbers suggest, though the numbers are the factual record of what happened on the field, and a .674 OPS isn't good.

Despite the team's numerous and obvious problems, GM Brian Cashman is likely to return in 2024 for what would be his 27th season on the job. On one hand, the Yankees have never had a losing season under Cashman and almost always finish with one of the league's best records. On the other hand, the current roster suggests fresh eyes and fresh perspective are needed.

Cashman and the Yankees did what amounted to a big-market rebuild in 2016. They traded away veterans at the deadline (Carlos Beltrán, Aroldis Chapman, Andrew Miller, Iván Nova) and played youngsters down the stretch (Judge, Gary Sánchez). In 2017, the Yankees surprised and went all the way to Game 7 of the ALCS. They have not gotten that close to a pennant since.

Another big-market rebuild year seems unlikely in 2024 -- Cole and Judge will be in their primes only so much longer and you can't waste those years -- but it does feel necessary. How did it get to this point? How is it the Judge era Yankees peaked in 2017? Here, in no particular order, are five reasons the Yankees are where they are, which is at the bottom of the AL East.

1. CBT plans gone awry

After going to Game 7 of the ALCS in 2017, the Yankees were in an enviable position. They had an MLB roster with a lot of young talent (Judge, Severino, Sánchez, Greg Bird, Jordan Montgomery, etc.), Baseball America's second-ranked farm system, and as little money on the books as at any point in recent memory. Alex Rodriguez's and Mark Teixeira's contracts had expired and CC Sabathia's big-money years were over. The Yankees had young talent and money to spend. It was an exciting time.

The missteps began in 2018, the year after the Yankees fell one win short of a World Series berth. That season Yankees ownership, led by chairman Hal Steinbrenner, ordered payroll to come under the $195 million competitive balance tax threshold. The competitive balance tax, or CBT, is MLB's soft salary cap. It is intended to discourage runaway spending. Yankees ownership wanted to get under the CBT threshold to reset their tax rates since they had been a multiple time offender. 

In English, that means the Yankees cut payroll in 2018. They cut payroll rather significantly. Here are the team's CBT payrolls during the five-year period from 2016-20, per Cot's Baseball Contracts.

2016

$243.7 million

2nd

2017

$224.2 million

2nd

2018

$193.0 million

6th

2019

$234.6 millon

3rd

2020

$239.8 million

1st

The Yankees lowered their CBT payroll by $31.2 million one year after going to Game 7 of the ALCS. Granted, the Yankees had a $193 million payroll in 2018 and that's a ton of money, but a 14% reduction in payroll the year after getting this close to the World Series? That's something that would enrage any fan, and it creates questions about ownership's commitment to fielding the best possible team. Getting that close to a pennant is the time to go all-in, not scale back.

The defenses of the 2018 CBT plan were not particularly compelling. Cashman said the Yankees wanted to stay under the CBT threshold "to not line the pockets of opponents to use that (revenue) against us," referring to CBT penalty dollars being distributed to non-CBT paying teams. It is true non-CBT paying teams get a portion of the CBT penalty money, but they don't get all of it. From Article XXIII(H)(2) of the 2017-21 collective bargaining agreement:

(2) 2017-21 Competitive Balance Tax Proceeds

(a) The first $13 million of proceeds collected for each Contract Year shall be used to defray the Clubs' funding obligations arising from the Major League Baseball Players Benefit Plan Agreements.

(b) 50% of the remaining proceeds collected for each Contract Year, with accrued interest, shall be used to fund contributions to the Players' individual retirement accounts, as provided in the Major League Baseball Players Benefit Plan Agreements.

(c) The other 50% of the remaining proceeds collected for each Contract Year, with accrued interest, shall be provided to Clubs that did not exceed the Base Tax Threshold in that Contract Year.

In 2017, five teams paid a combined $61.15 million in CBT penalties, with $36.2 million coming from the Los Angeles Dodgers. The Yankees contributed $15.7 million of that $61.15 million. So, per the CBA, the first $13 million of the $61.15 million went to the player benefit plan, and 50% of the remaining $48.15 million was distributed to the 25 non-CBT paying teams, or roughly $963,000 per team. That's a nice chunk of money in the real world, but in the baseball world, it's not much, and the Yankees didn't even pay all of it.

It was also argued getting under the CBT threshold in 2018 would put the Yankees in better position to pursue Bryce Harper and/or Manny Machado during the 2018-19 offseason. I suppose that's true, but not only did the Yankees not sign Harper or Machado, they never made Machado a formal offer and never even contacted Harper during free agency. One of the primary benefits of staying under the CBT threshold is lesser penalties for signing a qualified free agent, and the Yankees didn't sign any qualified free agents that offseason. The purposes of getting under the CBT threshold was what, exactly?

The Yankees raised payroll in 2019 and again in 2020, but it was still below its 2016 level, and the Yankees went under the CBT threshold again in 2021. When the Yankees signed Cole in Dec. 2019, Steinbrenner said, "We need to win some world championships ... plural." A year later the Yankees cut their CBT payroll by 14% to get under the threshold. Cutting payroll runs counter to whole "we need to win some world championship ... plural" thing. The Yankees blamed the pandemic, but a) other teams raised payroll from 2020 to 2021, and b) their 2017-18 actions are a reason to doubt their stated intentions.

Also, because the Yankees have prioritized the CBT, they have structured several contracts in a way that lowered the player's CBT number (CBT is based on the average annual value of the player's contract) but were a negative for the team overall. When LeMahieu became a free agent after 2020, the going rate for an above-average 30-something infielder was four years and $90 million (roughly Josh Donaldson's contract). They stretched the $90 million out over six years to lower LeMahieu's CBT number from $22.5 million to $15 million, though he's now signed through 2026 rather than 2024.

When the Yankees extended Aaron Hicks in Feb. 2019, the going rate for an above-average center fielder was five years and $80 million or so (Lorenzo Cain's and Dexter Fowler's contracts), and the Yankees stretched a five-year deal worth $70 million across seven years to lower the CBT number from $14 million to $10 million. New York released Hicks earlier this year and have to pay him through 2025 when a standard five-year contract would have expired after this season. These unwanted contracts will be on the books a lot longer than they need to be simply because the front office was trying to navigate ownership's CBT mandate.

Thanks to Judge & Co., the Yankees returned to prominence in 2017, and ownership's response was cutting payroll in 2018. And getting under the CBT threshold in 2018 has had no obvious on-field benefit. The Yankees have spent a lot -- A LOT -- of money on payroll the last two decades, but there was a significant reduction at a crucial time in 2018. The Yankees never put the pedal to the floor when the Tampa Bay Rays were regrouping and the Baltimore Orioles were a punchline, and now the AL East is much more competitive. The Yankees are the only team in the division with an arrow pointing down.

The problems start at the top. When the championship window opened in 2017, the first thing Yankees ownership did was reduce payroll. How they defend the decision to reduce payroll it is irrelevant. They did it and it is something that runs counter to putting the best team on the field. Cutting payroll intermittently meaningfully subtracted from New York's World Series odds.

2. Money poorly spent

Again, even with the CBT plans, the Yankees have spent a ton of money on their roster over the years. They have led baseball in payroll just once since 2014 (the 2020 pandemic season), though they're pretty consistently in the top three. This year only the New York Mets have a higher payroll than the Yankees, who have a $291.0 million CBT payroll and a $277.7 million payroll in actual dollars. The way that money has been allocated is a problem, putting it mildly.

Last year's Donaldson/Isiah Kiner-Falefa trade with the Minnesota Twins is perfectly emblematic of the Yankees' problems. They did not want to sign a prime-aged free agent shortstop (namely Carlos Correa or Corey Seager), in part because the end of long-term contracts tend to be ugly, so they instead tried to thread the needle with Kiner-Falefa, who is a fine utility guy that gets exposed with everyday play, and Donaldson, a 36-year-old making big money. What they acquired in Donaldson was what they feared getting stuck with had they signed Correa or Seager: an aging player making big money.

Not only did the Yankees fail to address their shortstop need and assume the large contract of a declining player with the trade, taking on Donaldson's contract allowed the Twins to sign Correa to what proved to be a bargain one-year contract. The Yankees tried to be the smartest team in the room and wound up with high-priced and ineffective players, allowing the other team to sign one of the game's top players. Think the Yankees could've used Correa's 138 OPS+ and 5.5 WAR in 2022? Yeah, me too.

Here are the Yankees' seven highest-paid players this year. Other than Cole and Judge, it's a lot of money for not much production:

RF Aaron Judge

$40 million

3.0

SP Gerrit Cole

$36 million

4.7

SP Carlos Rodón

$27 million

-0.5

3B Josh Donaldson

$25 million

-0.1

DH Giancarlo Stanton

$22 million

0.1

1B Anthony Rizzo

$20 million

0.6

IF DJ LeMahieu

$15 million

0.6

Judge has been excellent around his fluke toe injury and Cole has been amazing since Opening Day. He's been the best pitcher in baseball and is money well spent. Everyone else? Yeesh. The Yankees are paying impact player prices for guys putting up role player numbers, all of whom are on the wrong side of 30 and three of whom (LeMahieu, Rodón, Stanton) are signed through at least 2026. How are the Yankees supposed to build their roster around those guys the next few seasons?

I generally think Stanton is unfairly maligned -- his CBT salary is "only" 43rd highest in baseball this year and the Yankees gave up nothing to get him in a salary dump trade coming off his NL MVP year in 2017 -- and the Yankees made that trade knowing the end of the contract would be ugly. They did it to get the elite years up front, which they never quite got because of injuries, and the Yankees made matters worse by cutting payroll in 2018. Think about it: the Yankees added Stanton's massive contract in 2018 and still managed to cut payroll by $31.2 million.

The lesson: sign elite in-their-prime players when they become available. Harper, Machado, and Seager hit free agency at ages 26-27, meaning their contracts came with peak years in bulk, and the Yankees passed on them in favor of stopgaps like Donaldson and Kiner-Falefa and a small army of ineffective left fielders. Correa too. Once he was willing to take a one-year guarantee for 2022 (the Yankees were aware of that, per the New York Post), how do you not jump on it? The Yankees got cute and tried to cut corners when the obvious solutions were right in front of them, and they wound up with a bloated payroll anyway.

3. Young hitters stalling out

In the grand scheme of things, this is the single biggest reason the Yankees have been unable to get over the hump the last few years and are now at the beginning of what looks like a down period. So many of their young hitters and top prospects reached the big leagues, had immediate success, then stalled out or went backward. Judge is the obvious exception. He is one of the 4-5 best players in the world. Gleyber Torres has settled in as an above-average player who is short of being truly great, and that's really it.

Bird, Miguel Andújar, and Clint Frazier were all highly regarded former top 100 prospects who had immediate success in the big leagues -- Andújar finished second to Shohei Ohtani in the 2018 AL Rookie of the Year voting -- but could not sustain it for one reason or another (injuries, etc.). Sánchez belongs in this bucket as well. He was one of the game's best catchers from 2017-19, then everything just started to fall apart. Look at his career path:

2016

53

20

168

3.0

2017

122

33

126

4.0

2018

89

18

89

1.1

2019

106

34

119

3.1

2020

49

10

70

-0.3

2021

117

23

99

0.7

Sánchez played through a shoulder injury that required offseason surgery in 2018 and he bounced back nicely in 2019. He was the 2016 AL Rookie of the Year runner-up, a deserving All-Star in 2017 and 2019, and then his game went backwards at an age (27 in 2020) when players typically have their best seasons. Sánchez has at least rediscovered some semblance of his old self this year (15 homers and 1.4 WAR with the San Diego Padres), unlike Andújar, Bird, and Frazier.

Not every prospect works out and not every young player can live up to the high standards set early in their careers. Look at the list of Rookie of the Year winners. It's littered with players who had 1-2 great years to start their career, then petered out. When it happens once or twice, that's baseball. When it happens three times, it starts becoming a trend, and when it happens with four good young players in a short period of time as it did with the Yankees, it's time to ask what's going on. The players deserve some share of the blame, they're the ones on the field playing the game, but the Yankees have to look in the mirror too.

4. Lessons not learned

There are times it seems like the Yankees don't hear themselves talk. For example, Boone refers to "lanes" for his relievers, meaning pockets of the opposing lineup where certain relievers match up best. This goes back to at least 2019. Finding situations and matchups that best use the skills of your relief crew is smart business and something every contending team does. The Yankees are not unique in this regard, and they've typically had very good bullpens the last 10 years or so.

The thing is, the Yankees have built such a right-handed dominant offense the last few years that their lineup has become one big lane for the opposition. The Yankees find lanes for their relievers yet seem unconcerned about lanes for opposing relievers. Repeatedly from 2018-22, their offense was shut down by hard-throwing righties in the postseason because they lacked the lefty bats to match up. Look at the starting lineups for their final games in 2019, 2020, and 2022 (the Yankees were one-and-done in the 2021 Wild Card Game):

1. 1B DJ LeMahieu, RHB

1. 2B DJ LeMahieu, RHB

1. CF Harrison Bader, RHB

2. RF Aaron Judge, RHB

2. RF Aaron Judge, RHB

2. RF Aaron Judge, RHB

3. 2B Gleyber Torres, RHB

3. CF Aaron Hicks, SHB

3. 1B Anthony Rizzo, LHB

4. DH Edwin Encarnación, RHB

4. DH Giancarlo Stanton, RHB

4. DH Giancarlo Stanton, RHB

5. LF Giancarlo Stanton, RHB

5. 1B Luke Voit, RHB

5. 2B Gleyber Torres, RHB

6. CF Brett Gardner, LHB

6. 3B Gio Urshela, RHB

6. 3B Josh Donaldson, RHB

7. C Gary Sánchez, RHB

7. SS Gleyber Torres, RHB

7. LF Oswaldo Cabrera, SHB

8. 3B Gio Urshela, RHB

8. LF Brett Gardner, LHB

8. SS Isiah Kiner-Falefa, RHB

9. SS Didi Gregorius, LHB

9. C Kyle Higashioka, RHB

9. C Jose Trevino, RHB

That's 24 individual lineup slots between the three years and 18 went to right-handed batters, with two of the other six going to late-career Gardner. And it's not just that the lineup has been overloaded with righties. It's been overloaded with similar righties like Judge and Stanton and Encarnacion and Voit and Donaldson. Righties with power who are prone to swinging and missing. One or two of those guys is fine, especially when one is Judge. But three or four or five? It's too much.

It is confounding the Yankees have fielded such a right-handed heavy lineup despite playing their home games in Yankee Stadium, where the short right field porch is so inviting for left-handed batters. They rank 28th in plate appearances by left-handed batters this season and 27th since 2017. The Yankees continue to field such a right-handed heavy lineup even after the downside has been exposed year after year after year in the postseason. This is a major black mark on Cashman and the front office. An obvious multi-year problem is still a problem.

The Yankees have failed -- repeatedly -- to diversify their offense during the Judge era. Call it arrogance, call it ignorance, call it whatever you want (I lean toward arrogance more than ignorance because they're obviously aware of the importance of matchups given their bullpen usage). The point is, this has been an ongoing problem, and there have been few attempts to correct it. The game is telling the Yankees this isn't working and you have to change things, and they have not heeded those warnings.

5. Bad luck

Look, sometimes things just don't go your way. An errant fastball broke Judge's wrist in 2018 and he tore a toe ligament crashing into a small exposed concrete portion of the Dodger Stadium wall this season. The Yankees were planning an all-out pursuit of Ohtani when he first came over from Japan -- they traded for the maximum allowed amount of international bonus money -- and he was uninterested in the East Coast. He declined (respectfully) to even listen to their pitch. Severino got hurt (again and again), a rainout threw their rotation plans into a blender into the 2019 ALCS, so on and so forth.

Every team deals with bad luck though and I don't want to make excuses for the Yankees, Yes, they'd have their share of bad luck, but their resources also mean they are better able to overcome that bad luck than most teams. Bad luck played only a small role in their current plight. They've been unable to finish off the development of their top young hitter prospects, they've spent poorly when ownership wasn't randomly cutting back on payroll, and they have at best inadequately addressed their lineup imbalance, and at worst ignored it. The Yankees are where they are because they deserve to be here. They've stepped on landmine after landmine since 2017, many of them self-induced.

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