Yankees Exit Reopened A Painful Debate About Two Players They Gave Up On

Did the Yankees' decision to let Gary Sanchez and Randal Grichuk go cost them a chance at postseason glory?

The Yankees’ season ended the same way a lot of October games do: one run short, one bench answer missing, and another reminder that playoff value does not always come from a star turn.

New York dropped a 4-3 decision to Tampa Bay at Yankee Stadium on Wednesday, getting swept out of the American League Division Series. The Yankees managed seven hits but never found the last run they needed.

While that was unfolding, other clubs were squeezing production out of smaller roles. Milwaukee offered the cleanest example three days earlier at American Family Field, when it trailed San Diego 3-2 going to the ninth in Game 2 with Mason Miller lined up for a six-out save.

The Brewers scratched out a 4-3 win after three walks set the table and Jackson Chourio followed with a two-out, two-run single to center. Trevor Megill got the win; Miller was tagged with the loss.

That kind of inning is exactly why the Yankees’ decisions on two former players look different in October than they did when those calls were made. A reserve doesn’t have to be an everyday force to matter in a series. Sometimes all that’s required is a baserunner, a walk, a single, something that keeps the line moving.

Gary Sanchez gave Milwaukee that sort of moment.

The Brewers signed Sanchez to a one-year, $1.75 million deal in February 2026, and the Yankees did not bring him back. Just Baseball had identified New York as a possible fit in December, pointing to his power and a backup catching role, but that was only a proposed landing spot, not evidence of talks. Public reporting does not show whether the Yankees made an offer or even engaged his camp.

What Sanchez actually gave Milwaukee was a small but useful October contribution. In the Oct. 4 game against Miller, he worked a two-out walk on six pitches, including a full-count ball four, and loaded the bases for Chourio.

Across the regular season, he hit .209 with 12 homers, 38 RBIs, 47 hits and 37 runs in 86 games. His 112 OPS+ marked him as an above-average bat.

Milwaukee kept him as its second catcher after winning the NL Central at 103-59.

Randal Grichuk’s path with the Yankees was even shorter, and the contrast is hard to miss now.

New York used him for 31 at-bats over 16 games before designating him for assignment on April 29. He had started 0-for-15, then went 6-for-16, according to the New York Post.

Aaron Boone pointed to roster fit and positional flexibility when explaining the move. The Yankees opened room for pitching prospect Elmer Rodríguez’s debut and moved on from a right-handed bench bat just as the results were beginning to turn.

Grichuk chose free agency and signed with Chicago on May 1. With the White Sox, he hit .299 with 15 homers, 44 RBIs and a .926 OPS in 101 games while working in a platoon role. When asked in June about the experience, he said, “Definitely the most fun I’ve had in a long time,” Randal Grichuk said.

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

MLB’s updated numbers now list him at 3-for-12 with no homers or RBIs and a .558 OPS this postseason, after Cleveland won Games 3 and 4 to force a decisive Game 5 on Oct. 10.

The raw opportunity gap tells part of the story. Baseball Savant’s splits show Grichuk had 265 regular-season at-bats overall, with 31 coming for the Yankees and 234 for Chicago. New York accounted for 11.7% of his total, while Chicago gave him about 7.5 times as many chances.

That still doesn’t prove he would have produced the same way if he had stayed. It does, though, sharpen the question the Yankees now have to live with: whether a player can help in a narrower role even if he is not a fit as an everyday piece.

Sanchez’s Yankees résumé was longer and louder. He spent seven seasons in New York, made two All-Star teams and hit 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 created another possible reunion, but it never happened.

Neither Sanchez nor Grichuk is responsible for the Yankees’ exit. But both have already shown how much a little October value can matter, and that is the part New York has to weigh now that its season is over.

Milwaukee has moved on to face the Dodgers after a 3-1 clinching win over San Diego. Chicago’s run has shifted into a fight for survival.

The Yankees, meanwhile, are left to sort through two former players who found ways to contribute after leaving.

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