Jose Caballero's walk-off single propels Yankees into postseason
Sep 23, 2025; Bronx, New York, USA; Chicago White Sox second baseman Lenyn Sosa (50) hits a single against the New York Yankees during the second inning at Yankee Stadium. Mandatory Credit: John Jones-Imagn Images Jose Caballero hit a walk-off single in the ninth inning and the New York Yankees clinched a playoff berth with a 3-2 victory over the visiting Chicago White Sox on Tuesday night.
New York (89-68) won for the 20th time in 28 games and secured the 60th postseason appearance in team history when Caballero hit a bloop single to center field off Steven Wilson, capping a nine-pitch at-bat.
His hit also pushed the Yankees within one of Toronto (90-67) in the AL East after the Blue Jays fell to the Red Sox.
The Yankees tied the game in the ninth after Anthony Volpe scored on a wild pitch to the backstop by Brandon Eisert (3-7) on a walk to Cody Bellinger. Aaron Judge slid home from second for the winning run after drawing his second intentional walk.
Before Caballero gave New York its fifth walk-off win this season, the White Sox held a 2-1 lead as rookie Colson Montgomey hit a two-run homer with one out in the sixth off Luis Gil.
After Gil opened the inning by retiring Chase Meidroth, Kyle Teel hit a fly ball to right-center field. Center fielder Trent Grisham and Judge appeared to get confused on who was responsible for the catch and the ball fell between them for a single.
Three pitches later, Montgomery drilled a 1-1 changeup over the right field fence to give the White Sox the lead.
The Yankees faltered in clutch situations against relievers Tyler Gilbert, Jordan Leasure and Grant Taylor before getting their second win in 61 games when trailing through eight this season.
Jazz Chisholm Jr. was picked off before Gilbert struck out Volpe to end the sixth and Judge bounced into a double play to end the seventh. In the eighth, Amed Rosario struck out with runners at second and third following two singles and a wild pitch.
Austin Wells hit an RBI double in the second off Chicago rookie starter Shane Smith to give New York a 1-0 lead but the Yankees stranded nine before Caballero's game-winner.
In a possible audition for New York's postseason rotation, Gil allowed two runs and four hits in six innings. The right-hander struck out three, issued two and recovered from a 27-pitch opening inning.
--Field Level Media
Bengals Have No More Excuses Entering the 2026 NFL Season
MLB Player Props Today: Best Bets for Wednesday, July 22
Why the WNBA Won't Monetize Sophie Cunningham's Viral Point
What Prediction Markets Are Telling Us About NFL 2026 MVP
The Sacramento Kings Need to Blow It Up Before It's Too Late
- MLB Best Bets: Jacob Misiorowski, Dylan Cease Lead Monday's Top Picks
- Athletics vs. Diamondbacks Predictions: Best Bets, Odds and Props for Monday
- UFC Fight Night Best Betting Picks for Du Plessis vs. Usman in OKC
- France vs. England Best Bets: Three Picks for the World Cup Third-Place Match
- Dodgers vs. Yankees Friday July 17 Best Betting Picks and Props
- July 17 White Sox vs. Blue Jays Prediction, Odds and Best Bets
- Three MLB Futures Bets to Make After the All-Star Break

