There is a strong Cleveland-Toronto connection to the Blue Jays representing the American League in the World Series, and right at the top is Blue Jays president and CEO Mark Shapiro.

Shapiro, 58 years old, broke into professional baseball with the Cleveland Indians in 1991 as their player development director. He worked his way up to assistant general manager, general manager and then at the end of the 2010 season was named President of Baseball Operations.

Chris Antonetti was promoted to Indians general manager when Shapiro was named team president.

On Aug. 31, 2015, the Indians and Blue Jays jointly announced Shapiro would be leaving Cleveland at the end of the 2015 season to become president and CEO of the Blue Jays.

“Given the person that Mark is, the significant leadership and values that he has brought to the organization and with everything he has helped us accomplish, it will be extremely difficult to see him leave,” Guardians owner Paul Dolan said in a statement when Shapiro accepted the job with the Blue Jays. “However, I hope that this new challenge brings happiness and fulfillment for Mark and his family.”

Shapiro doesn’t run just the baseball side of the Blue Jays. He is also in charge of the business side of the organization. The only other baseball executive who has a similar dual role is Derek Falvey of the Minnesota Twins. Not coincidentally, Falvey broke into baseball as an intern with the Indians under Shapiro in 2007, working as an amateur and international scout.

Former player and manager Leo Durocher famously said, “Nice guys finish last,” when he was managing the Brooklyn Dodgers, but Shapiro is living proof nice guys can also finish first. For that matter, so in Antonetti, but this column is about Shapiro.

The Blue Jays are in the World Series for the first time since 1993. It is worth noting the Indians made it to the World Series in 2016, the season after Shapiro left, which is only to point out the Indians/Guardians did not fall apart without Shapiro’s leadership. Cleveland advanced to the wild-card series twice, the ALDS three times and the ALCS once after losing the 2016 World Series to the Cubs.

John Schneider has been managing the Blue Jays since 2022. They finished last in the AL East in 2024 at 74-88. A last-place finish three years into the job would have been enough for most team presidents to determine he needed a new manager. But Shapiro, who was never hasty when he was with the Indians, stuck with Schneider and general manager Ross Atkins, who has been on the job since 2015. The reward for his patience is the Blue Jays are the only team in the American League still playing baseball. The Jays finished 94-68 in 2025 to go from last to first in the East.

“In the face of a lot of criticism, and tough and bitter disappointment for us and our fans, we did a lot of soul-searching and made a determined effort to learn and get better from (2024),” Shapiro told sportsbusinessjournal.com. “Sports is the toughest environment to maintain patience and consistency, but it’s often rewarded because it gives you the ability to make adjustments when you do.”

The Blue Jays had the fifth-highest payroll in Major League Baseball in 2025 at $290,584,111. The Guardians were 25th at $118,169,450. When he took over in Toronto, Shapiro knew he’d have more money to spend on players.

The relationship between Antonetti and Shapiro has remained strong. In December, Antonetti traded second baseman Andres Gimenez to the Blue Jays in a deal that netted the Guardians starting pitcher Luis Ortiz from the Pirates. Ortiz in July was put on administrative paid leave by Major League Baseball while MLB conducts a gambling probe. The investigation is ongoing.

Antonetti traded starting pitcher Shane Bieber to the Blue Jays on July 31 for pitching prospect Khal Stephen.

Bieber started for Toronto in Game 7 of the ALCS. It has not been determined whether Bieber will get a start in the World Series.

Gimenez is playing shortstop for the Blue Jays in the World Series.

Ernie Clement, another former Guardians player, is also part of the Toronto roster.

I didn’t know that

… until I read my Snapple bottle cap.

The human brain weighs about three pounds. … The sun is white. Earth’s atmosphere makes it look yellow. … Flamingos turn pink from eating shrimp. They are gray as chicks. … A jiffy is an actual measurement of time equaling  1/100th of a second. … All planets rotate counter-clockwise with the exception of Venus. … The aphid insect is born pregnant.

Originally Published: October 25, 2025 at 2:20 PM EDT