2023 playoffs serve as a stinging reminder of Yankees of blunders

Fans react after the game between the Yankees and the Mets was postponed on July 2, 2021.

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The 2023 playoffs rub salt in the Yankees’ wounds with glaring reminders of their personnel gaffes and roster missteps. Despite the team’s absence from the MLB postseason for the first time since 2016, it’s impossible to ignore the presence of former Yankees players throughout the playoff field.

Many of those ex-Yankees were dumped by the team after failing to fulfill their potential during their time in New York. There are also many who had to seek greener pastures to unlock their true capabilities. But the most stinging ones for the Yankees are those who stood out as a significant source of disappointment in the Bronx but powered their teams once dumped unceremoniously.

When the Yankees find themselves unable to rejuvenate a struggling player who subsequently thrives elsewhere, it’s a matter of genuine concern. It is full of regret to see a problem that plagued the Yankees ends up resolving itself with another team.

For the Yankees, this postseason has served as a vivid reminder of their regrettable decisions. Let’s find out why and how.

Yankees rejected Bryce Harper, who flourishes with Phillies


Cashman’s choice to abstain from pursuing this prodigious talent is likely to linger as a haunting regret until the Yankees secure another World Series title. During the 2018-19 offseason, the Yankees found themselves on the fringes of the race for the two crown jewels of free agency: Bryce Harper and Manny Machado.

The Yankees decided to steer clear of Harper, despite his childhood allegiance to the team, while his free agency saga unfolded. Cashman explained to reporters during that offseason’s winter meetings that the Yankees’ outfield roster was already brimming with talent.

Cashman stated that throughout the winter, he never mentioned that he was seeking an outfielder. He mentioned several players, including Aaron Judge, Giancarlo Stanton, Brett Gardner, Aaron Hicks, Jacoby Ellsbury, and Clint Frazier, as part of the existing outfield options. He expressed surprise that people were still asking about the Harper situation.

Harper ultimately inked a fairly reasonable 13-year, $330 million deal with the Phillies. Initially, the Yankees’ decision to stay on the sidelines appeared to be a non-issue. DJ LeMahieu, an under-the-radar acquisition, outperformed both Harper and Machado in terms of OPS in 2019.

However, in the grand scheme of things, Harper has proven himself to be the quintessential generational superstar he was heralded as since his teenage years. He claimed the National League MVP title in 2021, spearheaded the Phillies to a pennant last season, and is currently battling the Braves in the National League Division Series this year.

Yankees pay to Aaron Hicks to power Orioles

The Yankees decided to part ways with Hicks, a move that was met with applause from the fanbase. Both the team and the Bronx faithful had grown weary of an outfielder whose performance between 2021 and his final game as a Yankee on May 19, 2023, included a dismal .209 batting average and a lackluster .625 OPS.

Aaron Hicks had never quite seemed to recover fully after undergoing wrist surgery in May 2021, ultimately losing his regular starting role—an experience he believed contributed to his continued struggles. He was designated for assignment despite having nearly $30 million remaining on his contract.

By the end of May, Hicks had signed with the Baltimore Orioles, and he immediately seemed like a transformed player, thriving away from a Bronx crowd that had consistently booed him.

From May 31 until the season’s conclusion, Hicks boasted a .806 OPS, outperforming nearly every Yankee in that timeframe except for Judge.

Yankees forced Aroldis Chapman to redeem himself elsewhere

Ex-Yankees pitcher Aroldis Chapman in pinstripes and Texas uniform.

The hard-throwing southpaw delivered numerous victories to the Yankees. However, his reputation suffered irreparable damage on two occasions: first as an individual due to his involvement in an alleged domestic violence incident that resulted in a suspension in 2016, and second as a player when he abandoned the Yankees just before last year’s playoffs by skipping a workout, effectively ensuring his omission from the postseason roster.

Aroldis Chapman inked a one-year, $3.75 million contract with the Royals, eventually being traded to the Rangers in June, and has largely outperformed his final days with the Yankees.

With a noticeably altered pitching delivery, the flame-thrower’s velocity has seen a significant uptick, with his average fastball velocity rising from 97.7 mph last year to an impressive 99.6 mph this year. Additionally, his ERA has taken a notable nosedive, plummeting from 4.46 in 2022 to a combined 3.09 in 2023.

The Yankees might want to reflect on why he has performed better and thrown harder for other teams.

Jordan Montgomery exemplifies Yankees’ worst trade decision

Jordan Montgomery is seen in both Texas Rangers' color and Yankees away uniform.

The Yankees made a trade with the Cardinals during the 2022 trade deadline, sending the reliable, though not yet outstanding, left-handed pitcher to St. Louis in exchange for Harrison Bader. This move was made with an eye on success in the postseason, as Bader was dealing with an injury but was expected to recover in time, which he did, and performed admirably during the playoffs.

At the time, it seemed unlikely that Jordan Montgomery would break into a postseason rotation that already featured the likes of Gerrit Cole, newly acquired Frankie Montas, Nestor Cortes, and Luis Severino.

However, the trade didn’t pan out as expected. Bader’s health and offensive performance never fully rebounded to their previous levels, while Montgomery thrived in St. Louis until the trade deadline this year when he was sent to the Rangers. Interestingly, Montgomery’s performance has improved further since joining the Rangers, boasting an impressive 2.79 ERA over 11 starts.

Yankees gave up Sonny Gray and Twins glad to have him

Sonny Gray in the Yankees pinstripes and Twins' uniform.

Here’s another unfortunate trade, this time occurring at the 2017 trade deadline. The Yankees struggled to bring out the best in Sonny Gray, who had previously thrived as an All-Star in Oakland. It’s unclear whether this was due to his makeup or pitch selection, but Gray’s tenure in The Bronx was marked by disappointment, lasting only a season and a half before the Yankees decided to cut their losses and trade him to Cincinnati. Interestingly, Gray immediately regained his All-Star form upon joining the Reds.

Following his departure from the Yankees, Gray pointed to the organization’s heavy reliance on sliders, a pitch he didn’t feel entirely comfortable with, as a major factor in his struggles.

Interestingly, it was Larry Rothschild, the pitching coach during Gray’s stint with the Yankees, who couldn’t seem to unlock Gray’s full potential. However, Gray has since excelled in three different locations and even earned an All-Star nod this season, posting an impressive 2.79 ERA while pitching for Minnesota.

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