Jorge CastilloSep 24, 2025, 12:59 AM ET
- ESPN baseball reporter. Covered the Washington Wizards from 2014 to 2016 and the Washington Nationals from 2016 to 2018 for The Washington Post before covering the Los Angeles Dodgers and MLB for the Los Angeles Times from 2018 to 2024.
NEW YORK -- José Caballero, a Yankee for all of 54 days, proudly carried a championship belt -- given to the player of the game after every New York victory -- around his left shoulder as alcohol-soaked chaos raged around him in the home clubhouse Tuesday night.
Acquired at the trade deadline to provide a versatile spark off the bench, the utility infielder fulfilled his duties to the max for the distinction: An inning after entering the game as a pinch-runner, Caballero swatted a two-out, walk-off single on the ninth pitch of his at-bat to lift the Yankees to a 2-1 victory over the Chicago White Sox and clinch the 60th postseason berth in franchise history.
"This is the best time to have the belt," Caballero said, "and I'm not letting it go."
Coupled with the Toronto Blue Jays' loss to the Boston Red Sox, the Yankees moved within a game of first place in the American League East with five games remaining. Toronto, however, holds the tiebreaker over New York. The Yankees would have to surpass the Blue Jays in the standings by the end of Sunday to claim their 22nd division title and earn a bye into the ALDS to begin their pursuit of a second consecutive AL pennant after falling to the Los Angeles Dodgers in the World Series last season.
"This October we're coming to prove a point," Yankees second baseman Jazz Chisholm Jr. said.
For now, the Yankees are guaranteed their eighth postseason appearance over the past nine years and their 26th trip in the 32 seasons since the playoffs were expanded to eight teams in 1994. Their magic number to clinch the top AL wild card spot -- and guarantee home-field advantage in a three-game wild-card series -- is three. The Yankees have not played in a wild-card series since it was first implemented in 2022.
"The ultimate goal is to win our division," Yankees right fielder Aaron Judge said as teammates bathed him with MVP chants and showered him with alcohol. "It's still right there for us. So, we're excited about getting in, but we got bigger things ahead of us."
The Yankees, despite boasting the third-most expensive roster in baseball, entered the season with pressing questions after losing Juan Soto to the Mets in free agency and Gerrit Cole to a season-ending UCL tear in spring training.
What followed has, so far, been a three-chapter tale. Their 42-25 record to start the season through June 12 was third best in the majors. From there, they went 22-31 through Aug. 12, tied for the seventh-worst mark in baseball. They then went 25-12 since Aug. 13, the best record in the majors, to ignite Tuesday's celebration and cut the Blue Jays' division lead by five games.
Challenges surfaced throughout the season. Oswaldo Cabrera's gruesome season-ending knee injury in May opened a gaping hole at third base that wasn't addressed until the trade deadline. Giancarlo Stanton didn't make his season debut until mid-June as he dealt with tendon injuries in both elbows. Clarke Schmidt, another rotation stalwart, joined Cole on the list of Tommy John surgery recipients in July. Luis Gil missed the season's first four months with a lat injury.
Anthony Volpe's struggles at shortstop and in the batter's box drew consistent boos all summer and, eventually, a dip in playing time. Devin Williams, acquired over the winter, lost his job as closer twice. Veterans DJ LeMahieu and Marcus Stroman were designated for assignment.
And, finally, the latest major blow: The flexor strain Judge suffered in his right arm in late July, which forced a 10-day trip to the injured list to interrupt his MVP-level campaign, limited him to designated hitter for a month upon his return, and has cast doubt over his ability to unleash full-effort throws from right field.
"It's been a challenging year, no question about it," Yankees manager Aaron Boone said. "But, at my core, and especially as we got here to the final couple months and then we got to the final month, I'm looking around in there and knowing that we're pretty healthy and getting guys back ... I [felt] like our best baseball was absolutely ahead of us and, hopefully, even still is ahead of us.
"But I think we're a really good club. It doesn't guarantee anything, but I'll certainly take our chances up against anyone."
The Yankees overcame the obstacles with a combination of internal development and external additions.
Trent Grisham emerged as the everyday center fielder with a career year. Cody Bellinger, acquired over the offseason to compensate for Soto's departure, gave the Yankees the left-handed bat they needed behind Judge while providing elite defense at four positions. Ben Rice solidified himself as a potent power hitter and a catcher the Yankees can trust. Rookie Cam Schlittler joined the rotation in July, just before the All-Star break, and didn't relinquish his rotation spot. Chisholm became the third Yankee to ever post a 30/30 season.
And at the deadline, general manager Brian Cashman, recognizing the roster was clunky and short on relievers, acquired three position players for more roster versatility and four right-handers to overhaul the bullpen.
"The depth is very impressive," Bellinger said. "Just the type of guys we got here, man. The culture here is very impressive, is very fun to be a part of. And we just believe in each other."
One of those position players added on the final day in July starred when it mattered most Tuesday night, putting together the kind of at-bat that wins games in October to send the Yankees to the postseason again for another chance at World Series title No. 28.
"We are coming for the big thing," Caballero said.
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