Attempting to defend their World Series title, the Los Angeles Dodgers will oppose a Toronto Blue Jays team that has far less Fall Classic experience. In his seventh MLB season, face of the franchise and ALCS MVP Vladimir Guerrero Jr. has reached this point for the first time, while the Blue Jays fanbase waited 32 long years to get back.

It has been an especially arduous journey here for Don Mattingly. More than 43 years after making his major league debut as a player, Toronto’s bench coach will make his World Series debut on Friday.

Mattingly has been tantalizingly close on numerous occasions. When he got called up by the perennially competitive New York Yankees in 1982, they were the reigning American League pennant winners. However, his playing career coincided with an uncharacteristic fallow period. Despite establishing himself as the AL’s best first baseman, Mattingly wouldn’t even get to appear in the postseason until 1995, his final season. Immediately after that, in 1996, the Yankees snapped their 18-year title drought and won it all.

Donnie Baseball t-shirt available at BreakingTMattingly officially retired in 1997 and was loosely connected to the Yankees organization during their ensuing dynasty as a special instructor. On the heels of yet another pennant in 2003, he was hired as their major league hitting coach. In his first year on the job, the Yankees took a seemingly insurmountable 3-0 lead over the Boston Red Sox in the 2004 ALCS, only to notoriously choke it away. He remained on their coaching staff through 2007—consistently qualifying for October, but never getting over the hump.

As manager of the Dodgers, Mattingly’s club was eliminated by the eventual NL pennant winners in both 2013 (St. Louis Cardinals) and 2015 (New York Mets). He stepped down from the position after five seasons. His successor, Dave Roberts, has led the Dodgers to five WS appearances since then.

Next, Mattingly became the winningest skipper in Miami Marlins history, though that’s not saying much. The Fish only finished above .500 once during his tenure (2020) and got swept out of the NLDS.

Now in his third year coaching with the Blue Jays, Mattingly is closer to a championship than he’s ever been before. As fate would have it, one of the few Jays players with World Series pedigree, George Springer, blasted the go-ahead home run in Monday’s pennant-clinching victory over the Seattle Mariners.

The Dodgers are favored to go back-to-back, though a superior regular season record earned Toronto home-field advantage. Rogers Centre hosts Game 1 of the World Series on Friday night.

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