Former Padres outfielder's last playoff run before free agency feels like unfortunate throwback

Trent Grisham's 2025 regular season was unfamiliar to San Diego Padres fans. Blasting a career-high 34 home runs - which doubled his previous best - as a New York Yankee this season, it looked like the former four-year Padre would catapult the Bronx Bombers to a deep postseason run.

Friars fans needed something to cheer for since they were eliminated in the Wild Card round by the Chicago Cubs, and thankfully, there were several former players still in postseason contention. All eyes were on Grisham, however, as the reigning World Series runner-up Yankees were looking to move by their AL East rivals in the Toronto Blue Jays. Grisham, a consistent leadoff hitter for the Yankees, was the perfect guy for Padres fans to root for, because, well, we all expected him to continue his new-found greatness at the plate.

He was dominant all season long, but unfortunately, Grisham fell short of his regular season successes in his first year with New York. Grisham batted 4-for-29 (.138) with 10 strikeouts in the playoffs, including an 0-for-5 effort with two punch-outs in Game 4 of the ALDS, which eliminated the Yankees from the postseason.

Grisham's brightest moment came in the game before they were bounced. In the bottom of the third inning at Yankee Stadium in Game 3 of the ALDS, Grisham led off with a double to spark a rally with the Bronx Bombers trailing, 6-1. He scored immediately on an Aaron Judge double to shift the momentum to New York's side as they went on to win.

Padres fans wish that Grisham had more in him, though. After batting south of .200 in each of his final three years with San Diego, it finally started to look like he was primed for a breakout. He was a regular season hero, but as we all know, the Yankees demand more than just regular season success from their players, and deservingly so.

Signed to a one-year, $5 million deal this past season, Grisham has become a free agent. We'll see where the two-time Gold Glover lands, and hopefully for him, his struggles in the playoffs will be overlooked.