TORONTO -- Over five decades of baseball, the major moments begin to stack up, each era having its own version of “where were you when …”
Early generations of Blue Jays fans tell stories of Exhibition Stadium and those cold, steel bleachers on Lake Ontario. Then came those great teams of the 1980s. Oh, how differently we might remember those years if there were three Wild Card spots in each league, but those rosters held some of the greatest collections of talent this organization has ever seen.
The early 1990s brought back-to-back World Series championships, and even in the two-plus decades that followed without a postseason appearance, we were all treated to the greatness of Roy Halladay and Carlos Delgado, two of the finest players to ever wear the Blue Jays’ uniform. Younger fans have their own heroes, too, from José Bautista and Josh Donaldson to Vladimir Guerrero Jr., George Springer and the 2025 team that jolted baseball back to life across Canada.
That 2025 run is still so fresh, but eventually, we’ll need to be reminded of moments like Addison Barger’s pinch-hit grand slam in Game 1 of the World Series, or when Davis Schneider and Vladdy busted open Game 5 in L.A. with back-to-back home runs on the first and third pitches of the game. We’ll remember the big ones, like Springer’s Game 7 American League Championship Series blast and Bo Bichette’s three-run shot in World Series Game 7 against the Dodgers, but there are so many others worth keeping alive.
The same goes for those teams of the 1980s, the World Series years and the return to glory in 2015 and ‘16. An organization with a history as rich as the Blue Jays’ has its Mount Rushmore moments, but it also has plenty of underrated moments from over the years that are worth remembering as this organization reaches its 50th year. Here are a few to start us off.
1. Dave Winfield’s double in Game 6 of the 1992 World Series
Arguably the most underrated moment in Blue Jays history, Winfield’s 11th-inning double in Game 6 of the 1992 World Series deserves to be on every nostalgia-fuelled highlight reel in Toronto for the rest of time. After Joe Carter’s walk-off home run at No. 1, it always takes a little too long to get to Winfield’s double when we discuss this organization’s biggest moments.
Winfield pulled the 3-2 pitch down the left-field line, past the Braves’ third-baseman, to score Devon White and Roberto Alomar. The eventual Hall of Famer had been brought to Toronto as a veteran bat to help take the lineup to the next level, and with the final swing of his lone season in Toronto, he cemented himself as a postseason legend.
2. Devon White’s triple in Game 4 of the 1993 World Series
Forget Blue Jays history, this was one of the best games in World Series history, a 15-14 win with a combined 32 hits over four hours and 14 minutes. This game should be part of the starter pack for young Blue Jays fans, and at the end of all the chaos, it was White who delivered the final blow.
Known as one of the greatest defenders in Toronto history, White did it with the bat this time. With the Blue Jays down, 14-13, in the top of the eighth, White looped a triple into the right-center alley to score Pat Borders and Rickey Henderson and give the team a one-run lead it wouldn’t relinquish.
3. Dave Stieb’s (and the Blue Jays’ ...) postseason debut
Those 1985 Blue Jays were so good. The outfield of George Bell, Lloyd Moseby and Jesse Barfield, all 25 years old, was a force. A young Tony Fernandez, just 23, was emerging as one of the best shortstops in baseball, and their rotation was led by the great Stieb and Jimmy Key (speaking of underrated …).
Stieb got the ball in Game 1 of the 1985 ALCS, the first postseason game in Blue Jays history, and delivered one of the finest performances of his career with eight scoreless innings, allowing just three hits and one walk while striking out eight. The heartbreak of that series (4-3 loss) still lingers for fans who remember, which included Stieb being hit hard in Game 7, but it felt like anything was possible after Game 1.
4. Candy Maldonado’s World Series Game 3 walk-off
Maldonado came to Toronto with loads of postseason experience from his days with the Giants, and in Game 3 of the 1992 World Series, it all paid off. With the series tied, 1-1, a Kelly Gruber home run in the eighth sent the game to the ninth tied at two.
Enter Maldonado, for whom the bases were loaded after Atlanta walked Ed Sprague in order to set up the double play. Instead, Maldonado took an 0-2 pitch and shot a line drive over the center fielder’s head, bringing home Alomar for the win.
5. Marco Estrada’s postseason heroics in 2015
That ALCS Game 5 performance in 2015 still feels special to watch back, though. The Blue Jays were down 3-1 in the series, still new to postseason success after 20-plus years stuck on the outside, and Estrada put his foot down. After pitching 7 2/3 innings of one-run ball at Rogers Centre, Estrada handed the ball to manager John Gibbons and walked off to one of the loudest ovations for a pitcher that the Toronto crowd has produced.