Yankees Legend Heading to World Series for First Time

Don Mattingly spent his entire playing career on the New York Yankees, but in 2025, he is going to the World Series for the very first time. With the Toronto Blue Jays. Yankees Videos shared the news on Twitter, as originally pointed out by MLB's Bryan Hoch.

Don Mattingly is headed to the World Series for the first time in his MLB career

(h/t @BryanHoch) pic.twitter.com/TqKA1niUIU
— Yankees Videos (@snyyankees) October 21, 2025

Mattingly's Playing Career

Mattingly played for the Yankees for 14 years from 1982 until his retirement in 1995, a famously conspicuous tenure in which the Yankees did not make the World Series (they appeared in 1981 and 1996, the year before and the year after Mattingly). The Yankees proceeded to enjoy a generational run without him, winning the World Series four times in his absence: 1996, 1998, 1999 and 2000.

It was clearly not for lack of talent or effort, as some current Yankees know all too well. Mattingly was a six-time All-Star for the team, selected every year from 1984–1989, a nine-time Gold Glove Award winner, and AL MVP in 1985. Mattingly is a certified Yankees legend, just one who never won a championship.

Mattingly Returned to New York as a Coach

Mattingly returned to the Yankees as their hitting coach in 2004, taking them to new heights and setting a record for home runs in a season with 242 (the current Yankees record is 306, set in 2019). He became a bench coach for them in 2006, and left after the 2007 season, an offseason in which he was passed over for the Yankees' manager role. He went on to serve as a coach with the Los Angeles Dodgers from 2008-2010, managed the Dodgers from 2010-2015, and managed the Miami Marlins from 2016-2022 before joining the Blue Jays' staff in 2023.

Future Yankees Manager?

Yankee fans have clamored to have Mattingly back in New York, specifically to take the place of controversial manager Aaron Boone, who is taking the heat once again as the Yankees miss another chance at a World Series win. The fanbase is bitter in defeat, and the Yankees are experiencing a 16-year drought since their 2009 World Series win. Donnie Baseball, on the other hand, is experiencing a dream come true with Toronto. The Blue Jays have not been to the World Series since 1993, and Mattingly of course has never been.

Aug 20, 2025; Pittsburgh, Pennsylvania, USA; Toronto Blue Jays bench coach Don Mattingly (46) looks on from the dugout against the Pittsburgh Pirates during the fourth inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

With their ALCS win, the Blue Jays will head to the 2025 World Series with the Dodgers, who won the NLCS in a sweep. The Dodgers defeated the Yankees in the 2024 championship, and the Blue Jays will have the opportunity to best them in 2025 with a Yankees legend in their corner.

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