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For nearly four decades, Don Mattingly has been one of baseball’s most respected figures, a former MVP, six-time All-Star, and manager known for his calm leadership and competitive fire. Yet, despite all his years in the game, one thing has always been missing: a trip to the World Series. As Sports Illustrated noted, that finally changed Monday night when the Toronto Blue Jays punched their ticket to the Fall Classic for the first time since 1993, defeating the Seattle Mariners 4-3 in a thrilling Game 7 of the ALCS. For most of Toronto’s young roster, this marks the start of a new chapter. For Mattingly, the team’s 64-year-old bench coach, it’s a long-overdue full-circle moment. “I’ve waited my whole career to get here,” Mattingly told reporters after the game. “You go through the highs and lows, but you never stop believing. This group never quit, and that’s what makes this special.” In a poetic twist, his first World Series appearance will come against the Los Angeles Dodgers, the very team he once managed but could never quite take to the Fall Classic. Mattingly’s Dodgers Run: So Close, Yet So Far Before joining Toronto’s staff in 2022, Mattingly spent five seasons managing the Dodgers from 2011 to 2015, where he helped guide the franchise back into postseason relevance. During that stretch, Los Angeles posted a 446-363 record (.551 winning percentage) under his leadership, winning three consecutive NL West titles from 2013 to 2015. Despite regular-season success, October heartbreak defined his tenure. Mattingly’s 2013 Dodgers came within two wins of the World Series before falling to the St. Louis Cardinals in the NLCS. In 2014 and 2015, Los Angeles suffered back-to-back heartbreaking Division Series exits. When the Dodgers parted ways with Mattingly after the 2015 season, it was framed as “mutual.” But for many, it felt like unfinished business. As The Athletic once noted, “Mattingly laid the foundation for the Dodgers’ modern dominance, but he just wasn’t there to see it peak.” He would later manage the Miami Marlins from 2016 to 2022, winning Manager of the Year in 2020 after leading a young roster to the playoffs in the pandemic-shortened season. Now, Mattingly will stand in the opposite dugout from the franchise that once defined both his opportunity and his frustration. World Series Matchup The Fall Classic is set to showcase some of baseball’s brightest stars with Shohei Ohtani, Vladimir Guerrero Jr., Freddie Freeman, and George Springer among them. “It’s two of the best rosters in baseball,” Blue Jays manager John Schneider said. “Both teams are built for October and know how to rise to the moment.” Toronto’s lineup has been a force from top to bottom. The Blue Jays ranked fourth in runs scored (847), first in team batting average (.281), and third in OPS (.794) during the regular season and they’ve only turned it up a notch during the postseason. The Dodgers, meanwhile, bring a pitching rotation that’s been nothing short of dominant. Blake Snell, Yoshinobu Yamamoto, Tyler Glasnow, and Shohei Ohtani have combined for an impressive 1.54 ERA in October, giving Los Angeles one of the most formidable staffs in recent playoff history. “We’ve been counted out all year,” Mattingly said. “But this group plays together. They believe in each other. That’s what championship teams do.” As the Fall Classic begins, Mattingly’s long journey finally leads him to baseball’s biggest stage as he faces the team that once let him go. Donny Baseball finally gets his chance to win it all, a dream he has been chasing his entire career.