I wasn’t upset when the Yankees lost Game 7 of the 2017 ALCS after blowing a 3-2 series lead. I had spent the previous four years watching the Yankees give full seasons of middle-of-the-order at-bats to late-career Vernon Wells and Lyle Overbay. I had seen only one postseason game during that time, a one-game shutout at home to the Astros. I was disappointed the Yankees’ 2017 season ended one win shy of the World Series, but the promise of what was to come prevented any sadness.
A team that wasn’t expected to reach the postseason won 91 games in 2017, erased a three-run deficit in the winner-take-all wild-card game and then erased an 0-2 series deficit in the ALDS against the top-seeded, 102-win team. They overcame an 0-2 series deficit in the ALCS, winning three straight games at home before falling short in Games 6 and 7. They had done all of this with a core of mid-20-somethings surrounded by a reliable cast of veterans in their lineup, rotation and bullpen. I wasn’t upset the Yankees came so close to the World Series and came up short because the future hadn’t been this bright for the organization in 20 years.
Then everything changed.
The Yankees moved on from Joe Girardi, citing a too-tense attitude and a disconnection with the current roster given the coddling needs of today’s players. Brian Cashman claims the Yankees were going to move on from Girardi even if they had won the World Series in 2017. I wish a guardian angel could guide me through an alternate reality like I’m George Bailey in It’s a Wonderful Life in which the Yankees win the 2017 World Series and change managers and then endure the kind of failure and humiliation they have since. Instead of promoting from within by naming career Yankee Rob Thomson — who George Steinbrenner wanted to one day manage the Yankees — the Yankees went with Aaron Boone and his impressive resume of zero coaching and managerial jobs at any level of baseball. Rather than lean into a team clearly capable of being a force in the league in 2018, Hal Steinbrenner cut payroll by $50 million.
Despite spending his entire life around not just baseball, but Major League Baseball, Boone managed like someone who had won a sweepstakes to achieve the position. The issues with Boone’s lack of experience began immediately in spring training when he tried to call Dellin Betances into a game even though he hadn’t asked Betances to warm up. Boone was given a mulligan by the umpires who let Betances warm up for as long as he needed to prevent injury in a spring training game. The issues never subsided, rearing their ugly head in the postseason.
In his first postseason, Boone’s starting pitcher didn’t know the start time of a pivotal Game 3. In that same game, Boone managed the Yankees to the most lopsided home postseason loss in franchise history. The next night, the Yankees’ season came to an end when Boone allowed CC Sabathia to face the entire Red Sox lineup a second time because he liked the matchup of Sabathia against the Red Sox’ light-hitting 9-hitter. The Yankees lost and Boone gave his first postgame press conference following an elimination game. At the time, no one knew it would become an annual occurrence. No one could have envisioned a championship-less tenure would go on this long. Following Wednesday’s Game 4 loss in the ALDS, I found myself watching Boone give his 2025 elimination press conference.
There’s nothing quite like a Boone postgame press conference following elimination. It’s masterful. It’s perfect in every way. Like Watching Wayne Gretzky operate from his “office” behind the net, Boone is most comfortable talking to the media after a Yankees season ends in disappointment because it’s the one thing he has more experience at without a championship to fall back on than any manager in Yankees history. No manager in the history of the Yankees has been given a fifth season on the job without a championship and Boone was just given his eighth. He has crushed the previous record and his eight-year run is now as unbreakable as Joe DiMaggio’s 56-game hit streak or Cal Ripken’s streak of 2,632 consecutive games played.
“When it ends this way,” Boone said. “It’s always terrible.”
It’s never ended any other way for Boone. Actually, that’s not true. There was the time two years ago when the Yankees posted their worst record in 30 years and weren’t eliminated from the postseason because they didn’t even make the postseason despite 40 percent of the league making it. Outside of that disastrous postseason-less year, it’s always ended this way for Boone.
“Winning the World Series is hard,” Boone said. “Been chasing it my whole life.”
Boone wouldn’t know how hard it is to win the World Series because he has never won it. He never won as a player and has never won as a manager. All he has are two American League pennants. One came from his home run, which served as the defining negative turning point in the Yankees-Red Sox rivalry and changed the course of history for the worst for the Yankees considering what the Red Sox have accomplished since Game 7 of the 2003 ALCS and because it led to Boone getting the job he still has. The other came against the easiest postseason field imaginable and was followed by a humiliating defeat in the World Series.
It’s unlikely Boone will ever stop chasing a championship. I can’t fathom a scenario where the Yankees win with him at the helm and no other self-respecting owner or general manager in the league with a ready-to-win roster would be foolish enough to hand the keys over to someone who has overseen such miserable disappointment. The idea Boone is good at his job because of his regular-season winning percentage at a time when half the league is tanking and pocketing profits or because he has made the postseason in seven of eight years at a time when 83-win teams are getting into the expanded format is comical.
Boone has created and fostered a culture comfortable with losing. His players recite the same tired lines they hear their manager use following losses. His players believe they can do no wrong performance-wise because they constantly hear their manager and the rest of the organization talk about how great they are. Cashman called the Yankees “pretty fucking good” after the team went 82-80 two years ago, so you can only imagine how he feels about a team that blew an eight-game lead over the Blue Jays, went 12-21 against the Blue Jays and Red Sox, bowed out in the division series, but won 94 games. Maybe Cashman will claim the 2025 Yankees as World Series champions the way he claims his 2017 team as World Series champions.
Boone frequently referred to his offense as “the best in baseball” this year as they consistently inflated their run differential against the league’s worst and then laid down to the league’s best. The best offense in baseball scored two runs or fewer in three of seven postseason games, couldn’t hit a splitter and were eliminated against an overworked, fatigued eight-reliever bullpen game. Boone constantly called the Yankees “the best team in the league” this year as well, so it’s unsurprising when Jazz Chisholm tells the media after a Game 4 loss (in which his own costly error put the game out of reach) that the Yankees were “the team to beat in the playoffs.”
The delusion and lack of accountability within the organization has spread through the clubhouse like hand, foot and mouth disease at a preschool and no player seems to be immune whether it’s a homegrown rookie, a veteran, a trade acquisition or a free-agent signing. Every Yankee except for possibly Giancarlo Stanton has been infected by the happy-go-lucky, Pollyanna way Boone has instilled in his team.
When the Yankees played the Red Sox on Sunday Night Baseball on June 8, Chisholm participated in an in-game interview with ESPN. When asked about Boone, Chisholm said, “We’re really good friends.” He didn’t say Boone is a “really good manager” or that “he’s great to play for.” No, the first thing that came to his mind was how good of friends they are. A manager has to have the ability to call out his players when they deserve to be called out. A friend? A “really good friend” isn’t about to call out their friend even if they deserve to be.
There is no score, game or situation that attracts urgency from the players, the manager or front office. Washed-up veterans are given exceedingly long leashes before being released, struggling closers are allowed to nearly ruin seasons and one player in particular has been treated like a Baseball God, receiving three full seasons of everyday playing time despite being the worst statistical everyday player in the majors during that time. With the outs coming off the board for the Yankees on Wednesday, Boone waited to use David Bednar, possibly saving him for Opening Day 2026, and called on Devin Williams and Camilo Doval first. Williams allowed two inherited runners to score and Doval gave up an earned run. By the time Bednar took the mound the Yankees trailed by four runs. Not even staring in the face of elimination is enough to create urgency for this manager.
I would never call for Cashman to be fired or replaced because it’s as likely to happen as the Yankees abandoning the interlocking NY — the most recognized sports brand in the world — as their logo. Cashman started with the Yankees 40 years ago as an 18-year-old, at the same time Hal Steinbrenner was 15. These two grew up together. They are essentially brothers. Cashman is a part of the Steinbrenner family in every way except for adopting the last name. The idea Cashman would ever be fired, removed or reassigned is not worth thinking about. One day Cashman will retire and leave the Yankees on his own terms and pick his successor before doing so, and that is the only way he will exit.
Hal Steinbrenner doesn’t want to be the public face owner of the Yankees. He wants to reap the benefits of owning the Yankees and increase his net worth, but he doesn’t want to be in the position he is in. It’s why his father planned to leave the team to be run by his son-in-law before a divorce ruined that and it’s why Hal’s brother was briefly the public face of the team before him. Hal is in the position he’s in out of necessity, not desire.
The last thing Hal would do is fire his “brother” and have to conduct a job search for a position that has been filled since Derek Jeter completed his second full season. The Yankees may not win championships, but they win in every aspect that matters to Hal. They led the AL in attendance, they made the playoffs, and they got five home playoff gates. The championship drought may get longer each year, but concession prices, ad revenue and ticket prices go up whether the drought exists or not. Business is good for Hal. Why would he want to disrupt what’s working for him in terms of massive, sport-leading revenues? He’s not an owner who invented some society- or industry-changing technology. He didn’t start a business in his garage and become a billionaire through decades of hard work and perseverance. Hal won the birth lottery. He doesn’t own the Yankees because he’s rich. He owns the Yankees because they are what makes him rich.
Because of this, Cashman has full control of the Yankees. Two years ago, when Cashman freaked out on the media after an 82-80 season, he said, “I’m here and Boonie’s here, and we’re not going anywhere,” and it was in that moment that every Yankees fan should have realized they’re screwed if they hadn’t already. Only after recognizing how outlandish he sounded did Cashman say that ownership has the power to change the manager and general manager if they want, but he made it clear that this is his team and his organization and the moron he has in the dugout is his moron and he’s not getting rid of him. Never for a day as Yankees manager has Boone thought it may be his last day as Yankees manager. Not when the team missed the postseason nor in any of their early postseason exits. When asked if he thought Game 4 may have been his last game as Yankees manager, Boone smiled, gave a sarcastic laugh and answered, “No, I’m under contract.”
Cashman and his smarter-than-everyone team annually construct a team built for a 162-game regular season in which they will face a lot of bad teams and bad pitchers. But when the schedule is shortened to just the league’s best teams and elite starters and high-end relievers, their 162-game roster is worthless. Their home run-or-nothing approach can’t win in October and their lack of contact bats who can work counts, foul off tough pitches and simply put the ball in play leaves them vulnerable to all-world breaking balls, high velocity and allows opposing starters to work deep into games. The offensive style the Blue Jays just used to destroy the Yankees is the style the Yankees used to play.
That was a long time ago. During Game 4, John Smoltz compared this Yankees era to his Braves career in which his Braves team only won once. At least they won once! This Yankees team has turned into a punchline, whether it’s the Red Sox using “New York, New York” as their victory song during their 2018 championship run, the Astros beating the shit out of the Yankees every time they have met in the postseason, the Dodgers embarrassing the Yankees on the field and then through the media for an entire offseason or David Ortiz and Vladimir Guerrero Jr. doing their own revised version of John Sterling’s “Theeeeeee Yankees win!” during a Yankees’ elimination celebration. The Yankees are only the Yankees in name at this point. A Yankees hat or a pinstriped home jersey used to signify winning and excellence. Now it’s signifies disappointment and failure. The brand of winning associated with the Yankees is fading because they don’t win anymore. 2009 was 16 years ago and 1996, 1998, 1999 and 2000 were forever ago. Once the Yankees retire Sabathia’s number, they will have exhausted every possible avenue to draw a sellout crowd for a mid-August game against the Royals unless they turn to Monument Park plaques for Brett Gardner, Joba Chamberlain and Nick Swisher for a revenue boost.
Four years ago, after the Yankees were embarrassed in the wild-card game at Fenway Park in a season in which they were the favorite to win the AL and instead finished third in their division and fifth in the AL, I wrote Yankees Need Organizational Change This Offseason. The big change was trading for Josh Donaldson for which the Yankees paid $51.5 million for a .678 OPS in 165 regular-season games and a .540 OPS in nine postseason games, and the ill-fated decision to acquire Isiah Kiner-Falefa to play shortstop. Following that wild-card game loss, Boone oddly talked about how “the league has closed the gap” on the Yankees. It was a confusing comment normally reserved to compare emerging teams to a recent champion, not a team at the time hadn’t won a championship in 13 years and now hasn’t won one in 16 years. It’s that kind of entitled lack of awareness by a manager who has never won anything and an organization that hasn’t won anything since the first year of the new Stadium that is disturbing.
When Cashman gave up on Sonny Gray after 2018 and traded him, he said, “I don’t feel like we can go through the same exercise and expect different results,” and yet, the Yankees continue to go through the same exercise every season during this era. Same manager, same type of players, and sure enough, same season-end result. The Yankees believe next year luck will be on their side in the postseason and they will finally overcome the odds of the crapshoot they have considered the postseason to be ever since they stopped winning it.
I fully expect the Yankees to “run it back” (as Aaron Judge mentioned he would like to do after Game 4) in 2026 with close to the same roster, the same failed organizational philosophies and certainly the same manager. And I fully expect another early postseason exit a year from now.
