Moments after the Chicago White Sox clinched a spot in the postseason, Andrew Benintendi was asked by CHSN if he was going to give any of the younger players in the clubhouse pointers on how to celebrate.
“It’s been a while for me,” Benintendi replied. “I’m going to have to teach myself again.”
When Benintendi signed with the Chicago White Sox in 2023, he was hoping to join a playoff contender.
The White Sox were coming off an 81-81 season in 2022, a year that began with the team as favorites to win the AL Central but ended with them 11 games behind the Guardians. Believing they were just a piece or two away from contending, the White Sox made Benintendi that piece, signing him to a franchise-record five-year, $75 million contract to bolster the outfield.
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In his first season with Chicago, Benintendi led the team with 147 hits, ranked second in games played, doubles and runs scored, and tied for second with 13 stolen bases. But the Chicago went 61-101, beginning a stretch of three consecutive 100-loss seasons Benintendi would endure in a White Sox uniform.
That included the infamous 2024 season, when the White Sox set a modern MLB record by losing 121 games.
The 2025 season brought more of the same, but the second half offered a glimpse of what was to come. Benintendi matched his career high with 20 home runs and became the first White Sox player since José Abreu to hit at least 20 in back-to-back seasons. Meanwhile, the young core general manager Chris Getz had been assembling started to show signs of what it could become.
That promise finally became reality in 2026.
Despite low expectations entering the season, the White Sox finished 84-78, just one game shy of the AL Central title, and punched their ticket to the Wild Card round. For Benintendi, the turnaround was especially significant. After enduring more than 300 losses over his first three seasons in Chicago, he was now the second-longest-tenured player on a team headed back to the postseason for the first time since 2021.
For Benintendi, the wait had been even longer. His last taste of October baseball came in 2018, when he helped the Boston Red Sox win the World Series.
Benintendi certainly wasn’t the biggest storyline or most impactful contributor to the White Sox turnaround, but his production was difficult to overlook. He spent most of the season in a platoon role at designated hitter, receiving the majority of his starts against right-handed pitching.
He slashed .240/.302/.413 with 15 home runs and ranked third on the team with 78 RBIs. All 15 of his home runs came against right-handed pitching, against whom he posted a .741 OPS. Paired with Randal Grichuk, who posted a 1.025 OPS against left-handers, the two formed one of the most productive designated hitter platoons in baseball.
It would have been easy for Benintendi to enter the season with a chip on his shoulder. He was still the highest-paid player in franchise history, had endured more than 300 losses during his first three seasons in Chicago, and was now being asked to accept a reduced role in a platoon.
Instead, he embraced his role, did everything Will Venable asked of him and became part of one of the most magical seasons in recent White Sox history.
For Benintendi, the celebration at Kauffman Stadium captured just how much had changed. The player who signed with Chicago expecting to play October baseball finally gets that opportunity again, this time alongside a young core that has transformed the White Sox from one of baseball’s worst teams into a postseason club.
And after all those years of waiting, perhaps the lessons Benintendi relearns while celebrating this postseason will come in handy as the White Sox try to make October last a little longer.
