Even though the Yankees’ season is over, the team’s disappointment is still very much on display.

Even though this is the first MLB playoffs since 2016, it features numerous ex-Yankees players.

Some people just couldn’t make it in New York.

Some people needed to go elsewhere in order to progress.

Some (well, one in particular) never wore pinstripes, but he still counts as a disappointment.

It’s concerning that the Yankees have been unable to help a player who has been struggling, only to see him flourish elsewhere.

It’s concerning when one team solves a problem that the Yankees have.

When the Yankees pass on a guy who ends up being worth every penny, it raises red flags.

The Yankees have plenty to worry about as they are constantly reminded of their mistakes on national television.

As the playoffs have become open season on Cashman and the Yankees, here are five examples:

The Phillies’ Bryce Harper

Cashman will likely regret not signing the phenom until the Yankees win another World Series.

The Yankees were a team on the fringes of the pursuit for free agency class stars Bryce Harper and Manny Machado.

Even though Harper was a lifelong Yankees fan, the team did not pursue him during free agency. Cashman informed reporters at the winter meetings that the Yankees already had enough outfielders.

Cashman stated, “At no time all winter have I said that I’m looking for an outfielder,” naming players such as Aaron Judge, Giancarlo Stanton, Brett Gardner, Aaron Hicks, Jacoby Ellsbury, and Clint Frazier. I’m astonished you’re still interested in the Harper stuff.

The 13-year, $330 million contract that Harper signed with the Phillies is actually rather affordable.

The Yankees’ inaction did not appear to have any negаtive consequences at first glance.

A relatively unknown signing, DJ LeMahieu, outperformed Harper and Machado in terms of OPS in 2019.

Long-term, Harper has resembled the type of generational superstar he’s been billed as being since he was a teenager.

He’s the National League’s most valuable player from 2021, and he’s currently leading the Phillies against the Braves in the National League Division Series.

The Orioles’ Aaron Hicks.

The Yankees’ decision to stop trying to sign Hicks was met with widespread approval from the fan base.

The Bronx faithful and the Yankees organization had grown tired of the outfielder’s.209 batting average and.625 OPS during the years of 2021 and 2023.

After undergoing wrist surgery in May 2021, he never truly recovered, and he lost his everyday role, which he claimed contributed to his further troubles. He was finally DFA’d with nearly $30 million still owed to him.

After signing with Baltimore at the end of May, Hicks seemed like a new player, finally free from the boos of Bronx fans.

Hicks’ .From the end of May to the end of the season, his OPS of 806 was higher than any other Yankee hitter’s (with the exception of Judge).

Rangers’ Aroldis Chapman

The dominant lefty helped the Yankees win a lot of games and acquire Gleyber Torres (from the Cubs in 2016).

He has also irreparably damaged his reputation on two fronts: first, as a person, for his alleged involvement in a domestic viоlence incident that resulted in a suspension in 2016, and second, as a player, for abandoning the Yankees in the days leading up to the playoffs by skipping a workout.

Before being dealt to the Rangers in June, Chapman signed a one-year, $3.75 million contract with the Royals and generally has been much better than his late Yankees days.

Changes to the fireballer’s delivery have resulted in a significant increase in velocity (from 97.7 mph in 2022 to 99.6 mph this year) and a significant decrease in ERA (4.46 in 2022 to 3.09 in 2023).

The Yankees need to figure out why he has been able to pitch more effectively and with more velocity elsewhere.

The Rangers’ Jordan Montgomery

With an eye on the postseason in 2022, the Yankees dealt the reliable but unspectacular lefty to the Cardinals at the trade deadline for Harrison Bader.

Bader was hurt, but it was expected that he would make a full recovery in time (and he did, excelling in the playoffs).

The Yankees had a deep rotation that included Gerrit Cole, recently acquired Frankie Montas, Nestor Cortes, and Luis Severino, thus it was unlikely that Montgomery would get into the postseason.

Bader’s health and bat never recovered enough to make the deal worthwhile.

Before being traded to the Rangers at the trade deadline, Montgomery had a 2.79 earned run average in 11 starts for St. Louis.

Gregorius Sonny Gray, of the Twins

Another disastrоus trade made at the 2017 deadline.

Gray’s All-Star performance in Oakland was never replicated for the Yankees.

Gray struggled for a season and a half in New York before the Yankees finally gave up and traded him to Cincinnati, where he promptly became an All-Star. This could have been due to Gray’s makeup or his pitch selection.

Gray blamed his problems on the Yankees’ faith in sliders, a pitch with which he was less familiar.

Gray, who has flourished in three other locations and was an All-Star again this season after posting a 2.79 ERA for Minnesota, had a pitching coach in Larry Rothschild who was unable to bring out his full potential.