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MLB playoffs rife with reminders of Yankees’ regrets

Tags: yankees harper

The Yankees’ season might have ended, but the regrets are still fully on display.

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

Some simply did not work out in New York.

Some had to go elsewhere to reach another level.

Some (well, one in particular) never actually donned pinstripes — but he surely qualifies as a regret.

When the Yankees cannot fix a struggling player and then watch him excel elsewhere, there is cause for concern.

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

When the Yankees stay out of the sweepstakes for a player who proves to be worth every penny, there is cause for concern.

There is plenty of concern for a Yankees club that is being reminded, on national TV, of potential missteps.

Here are five examples, as the postseason has doubled as open season on Cashman and the Yankees:

Bryce Harper, Phillies

The Yankees declined to make a serious run at Bryce Harper, watching him sign with the Phillies instead.Getty Images

A decision not to pursue the phenom probably will haunt Cashman until the Yankees win another World Series.

Back in the 2018-19 offseason, the Yankees hung on the periphery of the chase for the two 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 at that offseason’s winter meetings, the Yankees’ outfield was filled.

“At no time all winter have I said that I’m looking for an outfielder,” Cashman said, citing Aaron Judge, Giancarlo Stanton, Brett Gardner, Aaron Hicks, Jacoby Ellsbury and Clint Frazier. “The Harper stuff, I’m surprised you’re still asking.”

Harper wound up with the Phillies for what has become a reasonable, 13-year, $330 million contract.

In the short term, the Yankees’ inaction did not look like a backfire.

DJ LeMahieu, an under-the-radar signing, out-OPS’ed both Harper and Machado in 2019.

In the longer term, Harper has looked like the exact kind of generational superstar he has been hyped to be since he was a teenager.

He was the NL MVP in 2021, led the Phillies to a pennant last year and is fighting the Braves in the NLDS this year.

Aaron Hicks, Orioles

The Yankees gave up on Hicks, which mostly elicited cheers from the fan base.

The team and Bronx crowds were tired of an outfielder who, from 2021 until his last game as a Yankee on May 19, 2023, batted .209 with a .625 OPS.

He never quite looked right after needing wrist surgery in May 2021, eventually losing his everyday role — which he believed led to further struggles — and was DFA’d with nearly $30 million still owed to him.

By the end of May, Hicks had signed with Baltimore and immediately looked like a different player freed from a Bronx crowd that had consistently booed him.

Hicks’ .806 OPS from May 31 until the end of the season was better than every Yankee in that span except Judge.

Aaron Hicks looked like a different player once he escaped The Bronx.USA TODAY Sports via Reuters Con

Aroldis Chapman, Rangers

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

He also forever stained his reputation twice: first as a person for his role in an alleged domestic violence incident for which he earned a suspension in 2016, second as a player in abandoning the Yankees ahead of last year’s playoffs when he skipped a workout, which guaranteed he was left off the postseason roster.

Chapman signed a one-year, $3.75 million deal with the Royals, was traded to the Rangers in June and largely has been far better than his late Yankees days.

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

With a noticeably tweaked delivery, the fireballer’s velocity has been way up — last year’s average fastball was 97.7 mph, while this year’s was 99.6 mph — and ERA way down — from 4.46 in 2022 to a combined 3.09 in 2023.

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

Jordan Montgomery, Rangers

The Yankees traded the solid, if not yet spectacular, lefty to the Cardinals for Harrison Bader at the 2022 trade deadline with an eye on October.

Bader was hurt but projected to return in time (which he did, flourishing in the postseason).

It was hard for the Yankees to envision Montgomery cracking a 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 came around.

Montgomery was excellent with St. Louis until this year’s deadline, when he was sent to the Rangers and has been even better, posting a 2.79 ERA in 11 starts.

Sonny Gray, Twins

Another ill-fated trade, this one at the 2017 trade deadline.

The Yankees never could coax out the same Gray who emerged as an All-Star in Oakland.

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

In the aftermath, Gray cited the Yankees’ belief in sliders — a pitch he felt less comfortable with — as key to his struggles.

Larry Rothschild was the pitching coach who could not maximize Gray, who has thrived now in three other places and was an All-Star again this season, pitching to a 2.79 ERA with Minnesota.



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