Former World Series Champion Outfielder, Now a Free Agent, Wants to Return to the Yankees – “One Time Wearing the Pinstripes Again Is a Dream Before I Retire”

New York, NY – November 11, 2025
One of Major League Baseball’s most respected veteran outfielders — a former World Series champion and multiple-time All-Star — has publicly expressed his desire to return to the New York Yankees before hanging up his cleats for good.
The player in question? Andrew Benintendi, who last played for the Chicago White Sox and remains a free agent after his release earlier this year. A key contributor to Boston’s 2018 World Series title and a midseason spark for the Yankees during their 2022 playoff run, Benintendi says he still dreams of one last shot in the Bronx.

“Getting to wear the pinstripes again would be a dream before I retire,” Benintendi said in a recent interview. “There’s something about playing in New York — the energy, the fans, the tradition. I’ve been fortunate to experience it once, and I’d love nothing more than to finish my career there.”

Benintendi’s connection with the Yankees remains strong. During his brief stint with the team in 2022, he posted a solid .304 on-base percentage and earned praise for his steady defense and leadership in the clubhouse. However, a wrist injury late that season cut his momentum short, and he went on to sign with the White Sox the following year.
Now 31, Benintendi is healthy again and seeking a final opportunity to compete for a championship — and the Yankees, who have struggled to find consistent production in left field, could be an ideal destination.
While New York boasts stars like Aaron Judge and Anthony Volpe, the team has lacked a steady defensive outfielder to round out its lineup. A veteran presence like Benintendi — known for his contact hitting and postseason composure — could be exactly what the Yankees need heading into 2026.

“The Yankees are always built to win,” Benintendi added. “You see the roster, the history, the passion — that’s the standard every player dreams to be part of. If I get one more chance to help them chase a title, I’d take it in a heartbeat.”

At his best, Benintendi was one of baseball’s most complete left fielders — a career .276 hitter with a Gold Glove (2021) and over 80 outfield assists. His leadership and playoff experience could prove invaluable to a Yankees team looking to return to its championship identity.
With free agency heating up and New York expected to pursue veteran depth this winter, fans across the Bronx are already buzzing. And for Andrew Benintendi, one final chapter in pinstripes would be more than a comeback — it would be coming home.