Worrying history behind Aaron Boone’s 2023 Yankees pressure

Aaron Boone is the most unsuccessful successful manager in the majors.

He has been the Yankees skipper for five years. He has two first-place finishes — the only AL East titles for the organization in the past decade. Boone’s Yankees have never finished worse than second place and never missed the playoffs. Of the 211 men who have managed at least 700 games, Boone’s .603 winning percentage is fifth-best all-time.

But this hero of the 2003 Yankees-Red Sox ALCS shares similarities with a hero of the 2004 Yankees-Red Sox ALCS. Dodgers manager Dave Roberts’ .632 winning percentage is second-best. And unlike Boone, his Dodgers did win a World Series, albeit in the shortened 2020 COVID season.

In seven seasons, Roberts’ Dodgers have finished first six times. But they have won at least 104 regular-season games four times — setting or tying the franchise record for wins in each of the past three full years (2019, 2021, 2022), including 111 last season — and failed to win the World Series in any of those years. 

Roberts’ tenure is best known for failing to capitalize in the postseason and — correctly or incorrectly — for the public and media sense that he is merely a functionary orchestrating the desires of an analytically manic front office.

Los Angeles Dodgers manager Dave Roberts #30 on the dugout steps during a game at Citi Field against the New York Mets.
Dodgers manager Dave Roberts has led teams that have racked up wins but failed to win the World Series in a full season.
Charles Wenzelberg / New York Post

If that sounds familiar, you must have a favorite team in The Bronx.

I think this all renders capable people to caricature. The idea that Boone, for example, is just a cardboard cutout agreeing to whatever his bosses want is extreme.

However, I do wonder whether he is putting up enough of a roadblock when he perceives something is wrong or perhaps he is part of a groupthink that wasted time (and perhaps more) by insisting Gary Sanchez was a championship catcher and Gleyber Torres and Isiah Kiner-Falefa were championship shortstops. Because this is really about championships. 

Every decision cannot just be about the analytic card-counting that allows the Yankees to accumulate enough victories over the Royals and A’s in May and June to get to the playoffs — as valuable as that is. They also have to assemble the kind of team that can do more than beat the crap out of an overmatched AL Central opponent come the postseason.

Boone is in Year 6, and should have enough heft now to speak up if he doesn’t think Kiner-Falefa should be the shortstop or Josh Donaldson the third baseman or Aaron Hicks the left fielder or whatever he believes is stopping the Yankees from fulfilling the toughest mandate: excelling during the long season and having the fewest holes possible to survive the October gauntlet.

Because it is also Year 2 on a three-year contract extension for Boone. And though the Yankees have reversed the unsteady managerial legacy forged by George Steinbrenner by having just four managers in the past three decades, Boone begins this season as the member of the Yankees most in the crosshairs. Hal Steinbrenner will not be firing himself. Brian Cashman received a four-year extension this offseason. The players might get booed at home, but the contracts are guaranteed.

Brian Cashman and Aaron Boone of the New York Yankees chat on the field before the ALDS against the Cleveland Guardians.
GM Brian Cashman has a new four-year Yankees contract while Aaron Boone has two years remaining on his deal.
Robert Sabo for the NY Post

Perhaps Hal Steinbrenner and Cashman like and respect Boone so much that they will tolerate another postseason of beating the Guardians, losing to the Astros in five games and everyone talking afterward about how close they were to the promised land. But at some point the leadership is going to block out the noise by playing the “a new voice was needed” card.

Look, championships are incredibly difficult to win. Just look at Roberts’ Dodgers, whose run of success even predates him as manager. They are 10 for the past 10 in making the playoffs, first under Don Mattingly, then with Roberts. They have five of the 10 best single-season winning percentages in MLB in that decade-long span. They have won 73 more regular-season games than any other club — 931 to the runner-up Yankees’ 858. They have been the sport’s model franchise.

But there is just the one title from after the 60-game regular season.

The Yankees are at 13 years and counting without a championship. And what makes the upcoming season so treacherous is the postseason cannot be considered a layup even with six teams in each league gaining entrance and the Yankees sporting a franchise-record payroll near $290 million for luxury-tax purposes. Top to bottom, the AL East is the majors’ best division.

The Yankees, Blue Jays and Rays all have deep rosters. The Orioles have lots of volatility because their talent is young, but the talent is real. You can convince me the Orioles will win 75 games or that they will win 90 – their farm talent is rich enough that they could be a trade deadline force if they are in contention.

Baltimore Orioles catcher Adley Rutschman (35) flies out in the third inning against the New York Yankees at Yankee Stadium, Monday, May 23, 2022.
Adley Rutschman leads a young Orioles team that could sneak up on the AL East in 2023.
Corey Sipkin for the NY Post

And though the Red Sox have the most questionable talent base, they do have talent. Mostly, though, the Red Sox never make sense. They have finished last five times in the past 11 seasons, yet also won two titles. After the 2002 campaign, their offseason was perceived as underwhelming, filled with lots of accumulation without impact. Except there was a lot of impact. The Red Sox went to ALCS Game 7 in 2003 (the Boone game) and won it all in 2004.

After the 2012 campaign, their offseason was perceived as underwhelming, filled with lots of accumulation without impact. Except there was a lot of impact, and the Red Sox won it all in 2013.

It has been another 10 years. And after the 2022 campaign, their offseason has been perceived as underwhelming, filled with lots of accumulation without impact.

So, who knows?

Boone’s group has to navigate toward the top — if not the top — of this division, then finally assemble four weeks of postseason excellence. It is a perilous road. It is why in this ranking of the Yankees under the most pressure heading into spring training, the leadoff hitter in this nine-man lineup is the manager. The rest of the order:

2. Cashman. This is more his team than Boone’s. And one thing to remember is that in a quarter of a century as GM, Cashman never has assembled a clunker. There are no last-place finishes here like with the Red Sox — and the high draft picks that come with that.

But Cashman needs a championship like the Warriors had last year — the cherry on top 

that validates a great run. Cashman’s first three Yankees squads from 1998-2000 won it all, as did the 2009 club. To quiet the noise around him, Cashman surely could use another title, which would probably stamp a Cooperstown ticket as well.

Cashman has a lot of self-inflicted problems on this roster. Hicks’ seven-year, $70 million extension is the booby prize that keeps on giving. To date, uninspiring trades for Donaldson/Kiner-Falefa and Frankie Montas are creating 2023 headaches and headwinds. The position-player group remains overly right-handed. A bunch of trades have left a lot fewer rotation insurance policies. And it feels as if the time is now for Oswald Peraza and/or Anthony Volpe to exonerate the Yankees for staying out of the past two, starry free-agent shortstop classes.

New York Yankees starting pitcher Gerrit Cole #45 reacts after giving up a 2-run homer to Houston Astros center fielder Chas McCormick in the 2022 ALCS.
Gerrit Cole has been trending in the wrong direction during the early stages of his $324 million Yankees contract.
Charles Wenzelberg / New York Post

3. Gerrit Cole. As with Boone, there is a sense of someone being unsuccessfully successful. Cole has received Cy Young Award votes in all three of his Yankees seasons. He has been durable and missed bats at the highest level and been an above-average performer.

Yet there also has been something missing. Can Cole be explained by this 2022 reality: He led the majors in both strikeouts and homers allowed? His performance has declined in each Yankees season, and he has become more long-ball prone. And, while employed by the Yankees, he has become the face of pitcher usage of illegal sticky stuff, and his postseason performances have vacillated from high to low.

He still has six years left on a $324 million contract — which remains the most ever given to a pitcher. Is there a Cy Young in him? Is there a postseason run similar to what CC Sabathia had in 2009, the last time the Yankees won a championship? At his introductory press conference, he professed having the Yankees in his blood. But at this moment, the fans’ feelings toward the ace plays like a business relationship more than an emotional investment. 

4. Aaron Judge. Perhaps the 62-homer season after turning down a $213.5 million extension indicates Judge might be impervious to pressure. Still, there is naturally going to be a presiding sense of “what can he do for an encore,” especially after Judge signed a nine-year, $360 million deal.

New York Yankees owner Hal Steinbrenner walks on the field during Paul O'Neil Day at Yankee Stadium on August 21, 2022.
Yankees owner Hal Steinbrenner is now in the unfamiliar position of having the second-biggest payroll in town.
Jason Szenes for the NY Post

Judge has played in 305 of a possible 324 regular-season games the past two years. Since the Yankees offense goes as Judge goes until proven otherwise, his health is a key to the 2023 season.

5. Hal Steinbrenner. If it wasn’t bad enough for son of George that he has never been able to fully escape his father’s shadow, he now is going to be compared to Steve Cohen. The Yankees’ record payroll, for example, projects to more than $80 million less than that of Cohen’s Mets for luxury-tax purposes.

Being booed last September when Derek Jeter mentioned his name during a ceremony for Jeter’s Hall of Fame induction unnerved Steinbrenner. It perhaps gave Judge the best ammunition in his negotiation with the Yankees — knowing Steinbrenner recognized how much more unpopular he would become if he did not re-up the most popular Yankee since Jeter.

Steinbrenner sure could use a championship, too. Though it should be noted John Henry is the owner who helped end the Red Sox “Curse” in 2004 of not having won a title since 1918 and has been in charge for three more championships, yet Henry has been booed publicly this offseason by Red Sox fans who feel he has not invested enough emotionally and financially in the franchise in recent years.

Josh Donaldson #28 of the New York Yankees reacts after striking out during the ALCS against the Houston Astros.
Josh Donaldson has a lot to prove coming off a career-worst season and toting a big contract at the age of 36.
Charles Wenzelberg/New York Post

6. Donaldson. Cashman has proclaimed Donaldson the starting third baseman, though Donaldson is coming off his worst season. The Yankees GM has insisted it is not because the club still owes Donaldson $27 million, but rather because he fielded superbly last year and Cashman insists the bat will recover in 2023. But the combination of money and a personality that worries lots of organizations means, at 36, Donaldson does not have a ton of potential landing spots if the Yankees grow tired of his performance on or off the field. Donaldson, to some degree, is fighting for his career.

7. Volpe. Kiner-Falefa is the incumbent shortstop. Peraza — because he reached the majors and performed well in a cameo last year — might just be the favorite to start at short going into the season. But Volpe carries so many of the hopes and dreams of this organization.

The Yankees haven’t felt so good about the overall package of a prospect — skill and makeup — since perhaps Jeter. That is a lot of weight for someone who will not turn 22 until April 28. Many eyeballs will be on him in spring training to see what all the hype (and decision not to sign established stars) has been about.

8. Carlos Rodon. From 2017-20, Rodon was injury-prone and underperforming the talent that made him the third overall draft pick in 2014. In that time, he appeared in just 43 games (41 starts), going 11-17 with a 4.45 ERA, averaging 4.1 walks and 8.4 strikeouts per nine innings.

The past two seasons, Rodon has been as good as any pitcher. He is 27-13 with a 2.67 ERA in 55 starts, averaging 2.5 walks and 12.2 strikeouts per nine innings.

New York Yankees manager Aaron Boone assists pitcher Carlos Rodon with his jersey at his introductory press conference at Yankee Stadium on Dec. 22, 2022.
Carlos Rodon is set to don the pinstripes as he tries to maintain his two-year run of good health and dominant pitching.
Corey Sipkin for the NY Post

The Yankees invested $162 million over six years believing Rodon has unlocked the ability to stay healthy and thrive. In the 2008-09 offseason, the Yankees signed Sabathia for seven years at $161 million and A.J. Burnett for five years at $82.5 million.

Where on the Sabathia-Burnett spectrum will Rodon land? Will he be an ace lefty like Sabathia? Or, like Burnett, a talented guy who put together success and health to get the big free-agent deal, but could never fully harness the stuff in New York?

9. Hicks. There were other places to go for ninth in this order, including Harrison Bader and Luis Severino entering their walk years before free agency or DJ LeMahieu trying to come back from a foot injury or Oswaldo Cabrera attempting to prove his strong two-month debut last year was no fluke.

But Hicks and Donaldson are such hot-button issues, and both will feel intense scrutiny over whether they can be useful players. Hicks seemed to lose his nerve playing games in The Bronx last year. He was one of the worst home performers in the sport (.523 OPS, compared to .732 on the road).

The Yankees did not satisfactorily solve left field this offseason nor find enough lefty bats. In the ideal scenario, Hicks would be even league average in left field, allowing Cabrera to be used in a myriad of spots and giving Boone two switch-hitters to deploy regularly along with lefty Anthony Rizzo.

New York Yankees center fielder Aaron Hicks #31 bats against the Boston Red Sox on September 25, 2022.
Aaron Hicks’ numbers were noticeably worse in 2022 at Yankee Stadium, where he heard the complaints of Yankees fans.
Charles Wenzelberg / New York Post

I stumbled upon a stat that probably means nothing, but here it is: As a lefty hitter on the road, Hicks’ slashline was .279/.395/.416 in 186 plate appearances. There was not much power, but among players with at least 175 road at-bats as lefty batters, Hicks’ 16.1 percent walk rate trailed only Juan Soto (20.6), Max Muncy (19.9) and Lars Nootbaar (18.2), and Hicks struck out just 18.8 percent of the time.

And what did Hicks’ 143 plate appearances as a lefty hitter look like in the Yankee Stadium haven for lefty hitters? He had a .116/.252/.149 slash line with a 14 percent walk rate and 28 percent whiff rate. Hicks hit just one lefty homer at home — amazingly, it was a three-run shot off Astros closer Ryan Pressly in the bottom of the ninth on June 23 that tied the score 6-6 before Judge won it with an RBI single.

It feels as if the crux of getting performance out of Hicks begins with him finding a way to block the negativity that surrounds him in The Bronx. Is that even possible, or has the relationship deteriorated to such an extent as to make Hicks unsalvageable? Can the Yankees receive any signs in spring that Hicks will not crumble in The Bronx?

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