Don Mattingly Is Finally Heading to the World Series—Just Not With the Yankees

You know what they say about timing in baseball? Sometimes it’s everything. Sometimes it’s the cruelest joke the game has to offer. Don Mattingly, the guy whose swing was poetry and whose back gave out before the dynasty kicked in, is finally going to the World Series. At 64 years old. As the bench coach for the Toronto Blue Jays. If you’re a Yankees fan of a certain vintage, that sentence probably stings a little. Maybe a lot.

The Legend Of Donnie Baseball

Let’s rewind the tape. Mattingly wasn’t just good during his 14 years in pinstripes from 1982 to 1995. He was exceptional. Six All-Star selections. Nine Gold Gloves that could’ve been 10 if voters hadn’t been asleep at the wheel. An MVP award in 1985 when he hit .324 with 35 homers and looked like the second coming of Lou Gehrig.

He did all this while the Yankees were, let’s be honest, terrible. The mid-’80s to mid-’90s Yankees were a cautionary tale about what happens when George Steinbrenner meddles too much and the farm system runs dry. Mattingly gave everything he had to a franchise that couldn’t get him to October until his final season, when Edgar Martinez’s double sent him home in the 1995 ALDS.

The Yankees won the World Series the very next year. Then again in ’98, ’99, and 2000. Mattingly’s retirement party turned into the “Core Four’s” coronation. Talk about rotten luck.

The Long Road Back To October

After hanging up his cleats, Mattingly didn’t stray far from the game. He returned to the Yankees as hitting coach in 2004, helping them smash 242 home runs that season. He became a bench coach in 2006, clearly angling for the manager job that everyone assumed would eventually be his.

It never came. The Yankees passed him over after 2007, and Mattingly headed west to the Dodgers, where he coached and then managed from 2008 to 2015. He took the reins in Miami from 2016 to 2022, enduring the special kind of hell that comes with managing a Marlins team committed to losing. Now he’s in Toronto, working under Manager John Schneider—a guy who had Mattingly’s “Hit Man” poster on his bedroom wall growing up. The symmetry is almost too perfect.

How the Blue Jays Got Here

The Blue Jays weren’t supposed to be here, at least not according to the experts. They fell behind 2-0 in the ALCS against Seattle before clawing back with wins in Games 3 and 4. A heartbreaking Game 5 loss put them on the brink, but they won Games 6 and 7 at home to punch their ticket to the “Fall Classic.”

Mattingly has been instrumental in Schneider’s success, serving as the steady hand and experienced voice in a dugout that could’ve crumbled under pressure. Instead, the Blue Jays thrived, winning 94 games during the regular season and proving that chemistry and trust can carry a team further than talent alone.

“I’ve been telling people for about two months now, we’re gonna win it,” Mattingly said after the Game 7 victory, surrounded by family on the Rogers Centre turf. “You can feel it with this team. They’ve been a team all along.”

Yankees Fans Are Conflicted

If you’re a Yankees fan, this moment hits differently. On one hand, you’re thrilled for Mattingly. He deserves this. He gave his best years to a franchise that couldn’t deliver, and now he’s getting a shot at the ring that should’ve been his decades ago.

On the other hand, it’s with Toronto. The Blue Jays. An AL East rival. And while the Yankees are sitting at home after another postseason flameout, Mattingly’s getting ready to face the Dodgers in the World Series. The irony is thick enough to spread on a bagel.

What Happens Next?

The Blue Jays will take on the defending champion Dodgers, the team that knocked off the Yankees in last year’s World Series. Mattingly managed in Los Angeles for seven seasons, so this matchup carries extra weight. He knows that organization inside and out, and you can bet he’ll use that knowledge to his advantage.

Will Mattingly finally get his ring? Maybe. Maybe not. But the fact that he’s there at all after all these years, all the near-misses, all the bad breaks, feels like justice. Delayed, bittersweet justice, but justice nonetheless. And if the Blue Jays do win it all? Well, Yankees fans will have to decide whether to celebrate or cry into their chicken buckets. Probably both.