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Toronto Blue Jays: the 10 biggest mistakes in Blue Jays history

By David Salituro

DENVER, COLORADO - SEPTEMBER 18: Starting pitcher Noah Syndergaard #34 of the New York Mets throws in the first inning against the Colorado Rockies at Coors Field on September 18, 2019 in Denver, Colorado. (Photo by Matthew Stockman/Getty Images)
DENVER, COLORADO - SEPTEMBER 18: Starting pitcher Noah Syndergaard #34 of the New York Mets throws in the first inning against the Colorado Rockies at Coors Field on September 18, 2019 in Denver, Colorado. (Photo by Matthew Stockman/Getty Images) /
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TORONTO, ON – SEPTEMBER 11: Toronto Blue Jays fans display a sign in support of former general manager Alex Anthopoulos during MLB game action against the Baltimore Orioles at Rogers Centre on September 11, 2017 in Toronto, Canada. (Photo by Tom Szczerbowski/Getty Images)
TORONTO, ON – SEPTEMBER 11: Toronto Blue Jays fans display a sign in support of former general manager Alex Anthopoulos during MLB game action against the Baltimore Orioles at Rogers Centre on September 11, 2017 in Toronto, Canada. (Photo by Tom Szczerbowski/Getty Images) /

Blue Jays mistake No. 5: Letting Alex Anthopoulos walk away

Alex Anthopoulos is a Canadian boy made good. He started off as an intern for his hometown Montreal Expos before joining the Toronto Blue Jays scouting department in 2003. Rising through the ranks of the Blue Jays front office, he became general manager in 2009.

Anthopoulos was never afraid to make the bold move. One of his first acts as Blue Jays general manager was to orchestrate the trade of franchise ace Roy Halladay. Before the 2013 season, he acquired Mark Buehrle, Jose Reyes, and Josh Johnson from the Marlins, then got the reigning Cy Young Award winner, R.A. Dickey, in a deal with the Mets.

His moves came to fruition in 2015. He acquired third baseman Josh Donaldson, who went on to win AL MVP that season. On July 28, he traded Reyes to Colorado in a package that included Troy Tulowitzki. Two days later, he swung a deal with the Tigers for left-hander David Price. The Blue Jays were just a game above .500 at the time; they ended the season on a 41-18 run, best in the AL, and snapped a 22-year postseason drought.

Grateful Blue Jays fans showed their appreciation. As they were clinching the division title in a game against the Orioles, the Blue Jays fans who made the trip to Baltimore started an impromptu chant of “Thank you, Alex.” But it turned out to be Anthopoulos’ last year in Toronto.

The Blue Jays hired Mark Shapiro as team president in August. Shapiro and Anthopoulos immediately clashed, with Shapiro’s arrival closing the door on Anthopoulos taking over that same role in the organization. When he was offered a contract extension after the 2015 season, Anthopoulos turned it down and left the club.

His impact is still felt on the club in 2020. In July 2015, he signed a 16-year-old Vladimir Guerrero Jr. But Shapiro and Anthopoulos’ replacement, Ross Atkins, have completely dismantled the roster that made back-to-back ALCS appearances that he built. No player from those teams is still on the roster.

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