The MLB playoffs are rife with reminders of the Yankees’ grievances


The Yankees’ season may be over, but the grief is still there.

Still, the first MLB postseason without the Yankees since 2016 is filled with players from the Yankees’ past.

Some just didn’t work in New York.

Some had to go elsewhere to reach another level.

Some (well, one in particular) never actually wore pinstripes – but it’s certainly something to regret.

When the Yankees are unable to fix a struggling player and then watch him achieve success elsewhere, there is cause for concern.

When the Yankees’ problem becomes another team’s solution, there is cause for concern.

When the Yankees are not in the lottery and are looking for a player who proves to be worth every penny, there is cause for concern.

There are many concerns about the Yankees, who are being reminded on national television of their potential mistakes.

Here are five examples of when the postseason doubled as the open season for Cashman and the Yankees:

Bryce Harper, Phillies

The Yankees refused to make a major push for Bryce Harper, instead watching him sign with the Phillies.
Getty Images

The decision not to continue this phenomenon will likely haunt Cashman until the Yankees win another World Series.

In the 2018-2019 offseason, the Yankees were on the fringes of their pursuit of two of the gems of the free agent class in Harper and Manny Machado.

The Yankees stayed away from Harper, who grew up a Yankees fan, even as his free agency dragged on because, as Cashman told reporters during the winter offseason meetings, the Yankees’ outfield was full.

“I haven’t said once all winter that I’m looking for an outfielder,” Cashman said, citing Aaron Judge, Giancarlo Stanton, Brett Gardner, Aaron Hicks, Jacoby Ellsbury and Clint Frazier. “Harper stuff, I’m surprised you’re still asking about it.

Harper finished his career with the Phillies on a reasonable 13-year, $330 million contract.

In the short term, the Yankees’ inaction didn’t seem to backfire.

DJ LeMahieu, an under-the-radar addition, surpassed both Harper and Machado’s OPS in 2019.

In the long run, Harper looks to be exactly the generational superstar he has been promised to be since he was a teenager.

He was the NL MVP in 2021, led the Phillies to the relay last year and is facing the Braves in the NLDS this year.

Aaron Hicks, Orioles

The Yankees waived Hicks, much to cheers from fans.

The team and fans in the Bronx were tired of the outfielder, who was batting .209 with a .625 OPS from 2021 until his final game as a Yankee on May 19, 2023.

He never looked well after wrist surgery in May 2021, ultimately losing his everyday role – which he believes led to further struggles – and was DFAed while still being owed nearly $30 million.

In late May, Hicks signed with Baltimore and immediately looked like a different player, freed from the Bronx crowd that constantly booed him.

Hicks’ .806 OPS from May 31 through the end of the season was better than all Yankees during that period except Judge.

Aaron Hicks looked like a different player after escaping from the Bronx.
USA TODAY Sports via Reuters Con

Aroldis Chapman, Rangers

The powerful lefty brought plenty of wins to the Yankees and Gleyber Torres (in a 2016 trade with the Cubs).

He has also permanently sullied his reputation twice: first for his role in an alleged domestic violence incident, for which he was suspended in 2016, and second for abandoning the Yankees before last year’s playoffs when he left training, which guaranteed he was left off the postseason squad.

Chapman signed a one-year, $3.75 million contract with the Royals, was traded to the Rangers in June, and is largely doing much better than he was when he was with the Yankees late in his career.

The end of Aroldis Chapman’s Yankees came after he was left off the 2020 playoff roster.
Getty Images

Thanks to the noticeably improved delivery, fireball velocity has increased significantly – last year’s average fastball velocity was 97.7 mph, down from 99.6 mph this year – and the ERA dropped significantly – from 4.46 in 2022. to a total of 3.09 in 2023

The Yankees should probably ask themselves why he threw better and harder elsewhere.

Jordan Montgomery, Rangers

The Yankees traded a solid if unspectacular left winger to the Cardinals for Harrison Bader at the 2022 trade deadline, with an eye on October.

Bader was injured, but was expected to return in due time (which he did, flourishing in the postseason).

It was hard for the Yankees to imagine that Montgomery would crack the postseason rotation of Gerrit Cole, newly acquired Frankie Montas, Nestor Cortes and Luis Severino.

The trade did not work out as Bader’s health and bat never fully returned to normal.

Montgomery performed brilliantly for St. Louis until this year’s deadline, when he was sent to the Rangers and performed even better, posting an ERA of 2.79 in 11 starts.

Sonny Gray, Twins

Another bad trade, this time at the 2017 trade deadline.

The Yankees would never be able to bring out the same Gray who emerged as an All-Star in Oakland.

Maybe because of the makeup, maybe because of the pitch selection, Gray endured a poor season and a half in the Bronx before the Yankees admitted defeat and moved him to Cincinnati, where he immediately became an All-Star.

In the aftermath, Gray cited the Yankees’ faith in sliders – a pitch he was less comfortable with – as a key to his struggles.

Larry Rothschild was a pitching coach who was unable to maximize Gray’s level of success in three other spots, and he was an All-Star again this season, posting an ERA of 2.79 in Minnesota.

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