Two Former Yankees Give New York Reason To Regret Giving Up On Them
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Home News Ex-Yankees

Yankees’ lack of faith in two former players returns to haunt their flawed judgment

Inna Zeyger by Inna Zeyger
October 10, 2026 at 11:13 am EDT
in Ex-Yankees, News
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Pinch hitter Austin Wells gets hugs in the dugout after his second home run in the Yankees' 16-1 win over the Red Sox, New York, August 30, 2026.

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NEW YORK — The Yankees’ season ended with a one-run deficit and no answer from the bench. Elsewhere in October, contenders have kept innings alive and strengthened their lineups by finding value in limited roles.

New York lost 4-3 to Tampa Bay at Yankee Stadium on Wednesday, completing an American League Division Series sweep. The Yankees finished with seven hits but could not produce the final run they needed.

Three days earlier, Milwaukee had faced a similar late deficit at American Family Field. The Brewers trailed San Diego 3-2 entering the ninth inning of Game 2, with Mason Miller pursuing a six-out save.

Milwaukee won 4-3 when Jackson Chourio singled home two runs with two outs. Before that hit, three walks had changed the inning. The difference was a string of baserunners against an elite closer, followed by contact that reached center field.

That contrast puts the Yankees’ roster decisions in a different postseason context. A reserve does not need a full season of everyday work to affect a series. The available assignment might be one plate appearance, with the club needing him to reach base rather than deliver a homer.

For the Yankees, evaluating those assignments also means separating two questions: whether a player fits as a regular and whether he still offers something in a narrower role. A decision to move on can be defensible when made and still deserve another examination after the player produces elsewhere.

The evidence this October comes from different transactions, different timelines and different expectations. One involves a brief early-season opportunity. The other follows years of major league exposure. Treating both as identical mistakes would miss what their new clubs actually received and how those contributions now sharpen the comparison.

A $1.75 million deal turns into big October value

Gary Sanchez signed a one-year, $1.75 million contract with Milwaukee in February 2026. The Yankees did not bring him back.

Just Baseball identified New York as a possible landing spot in December, citing his power and a backup catching role. That was a proposed fit, not a report of negotiations. Milwaukee ultimately made the investment in his rebound. Public reporting does not establish whether the Yankees made an offer or held talks with his representatives.

Sanchez drew a two-out walk against Miller on Oct. 4, loading the bases for Chourio. He took all six pitches, including ball four on a full count. Trevor Megill earned the win; Miller took the loss.

He hit .209 with 12 homers, 38 RBIs, 47 hits and 37 runs in 86 regular-season games. His 112 OPS+ indicated above-average offense. Milwaukee kept him as its second catcher after winning the NL Central at 103-59.

Grichuk loses his Yankees spot despite signs of a rebound

The Yankees gave Randal Grichuk 31 at-bats across 16 games before designating him for assignment April 29. He had gone 6-for-16 after an 0-for-15 start, the New York Post reported.

Aaron Boone cited roster fit and positional flexibility in explaining the move. Grichuk’s departure cleared space for pitching prospect Elmer Rodríguez’s debut. New York cut its right-handed bench bat even as his results improved.

Grichuk elected free agency and signed with Chicago May 1. In 101 White Sox games, he hit .299 with 15 homers, 44 RBIs and a .926 OPS while filling a platoon role.

Asked in June about playing for Chicago, he described his enjoyment of the experience.

“Definitely the most fun I’ve had in a long time,” Randal Grichuk said.

Through Chicago’s first four postseason games, he had appeared in three and gone 2-for-6 with a walk and a run.

A 31-at-bat trial accounts for just 11.7% of his season

Baseball Savant’s splits show Grichuk had 265 regular-season at-bats: 31 for the Yankees and 234 for Chicago. New York accounted for 11.7% of the total; Chicago gave him about 7.5 times as many at-bats.

That measures opportunity, not what he would have produced if retained. Sanchez’s history was longer: seven Yankees seasons, two All-Star selections and 34 homers in 2019.

The Yankees traded Sanchez and Gio Urshela to Minnesota in March 2022 for Josh Donaldson, Isiah Kiner-Falefa and Ben Rortvedt. His 2026 free agency offered another chance at a reunion.

Neither player’s subsequent production proves his absence caused New York’s elimination. Both provide evidence of value in limited roles.

Yankees’ October path closed, but their remains open

Former Yankees big name Sanchez, with 201 career regular-season homers, extended Milwaukee’s rally without swinging. His assignment required another baserunner, not another home run.

As of Oct. 10, Milwaukee has advanced to face the Dodgers after a 3-1 clinching victory over San Diego.

Chicago’s position has changed since its unbeaten postseason start. Cleveland won Games 3 and 4, forcing a decisive Game 5 on Oct. 10. MLB’s updated statistics list Grichuk at 3-for-12 with no homers or RBIs and a .558 OPS this postseason.

The Yankees are in the offseason. Their former players have contributed in roles requiring less than everyday status, giving New York two cases to weigh during its roster review.

What do you think? Leave your comment below.

Tags: Chicago White Soxex-yankeesgary sanchezJackson Chouriomason millerMilwaukee BrewersMLB playoffsNew York Yankeesrandal grichukYankees roster
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Inna Zeyger is a staff writer for PinstripesNation contributing to breaking news stories as they happen. Being at the stadium for Jeter's last game

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