Bob File: The Reality of Playing Against Your Childhood Team

Every baseball fan dreams of stepping onto the field under the bright lights, but what happens when you make it to the majors and end up playing against the very team you grew up cheering for?

For former Toronto Blue Jays pitcher Bob File, that reality came full circle when he took the mound against the Philadelphia Phillies, the team he loved as a kid. As a native of Pennsylvania, File had spent his childhood watching the Phillies, only to later find himself standing opposite them in a major league uniform.

On Jay Bird Watching Podcast, File shared what that experience was really like, along with fascinating insights into ballpark atmospheres, pitching matchups, and the mental approach of facing a team you once idolized.

For the full podcast episode, please go to youtube.com/@birdwatchinggc and subscribe for future updates. Audio can be found on any site you receive your podcast pleasures from as well.

Growing Up a Phillies Fan & Making It to the Majors

Like many kids growing up in Pennsylvania, Bob File was a die-hard Philadelphia Phillies fan, following legendary players like Lenny Dykstra, John Kruk, and Darren Daulton. Watching the Phillies reach the 1993 World Series against Toronto, File never imagined he’d one day be pitching in the major leagues himself—let alone against Philadelphia.

After grinding through the minor leagues, File eventually reached the majors with Toronto in 2001, beginning a career that would place him on the mound facing the very team he once idolized.

!!!!add bobs story for being ejected here!!!!

Facing the Phillies: The Ultimate Test

One of the most surreal moments for File came when he first stepped onto the mound against Philadelphia. Suddenly, the players he had once cheered for as a kid weren’t just highlights on TV—they were standing in the batter’s box, ready to take him deep.

“The first time I faced them, it was crazy. I spent my childhood watching these guys, and now I’m supposed to get them out,” File said.

He recalled how facing off against Phillies hitters forced him to detach from the emotion of the moment and focus on execution.

“You can’t think about it like that. Once the game starts, it’s just another team—another hitter I need to get out.”

SkyDome vs. Citizens Bank Park: Ballparks & Matchups

Playing for Toronto, File experienced one of baseball’s best hitter-friendly environments—SkyDome (now Rogers Centre).

During the podcast, he explained why hitters thrive at the Rogers Centre, noting that Carlos Delgado once told him it had one of the best batter’s eyes in baseball, making seeing pitches easier and leading to more offense.

Conversely, Citizens Bank Park, which didn’t exist during File’s playing days, has become another hitter’s paradise, especially with Philadelphia’s power-packed lineup featuring Bryce Harper, Kyle Schwarber, and Trea Turner.

“When you’re pitching in a homer-friendly ballpark, the game changes. You know that a simple mistake—three inches too high or too low—could turn into a home run,” File explained, referencing Harper’s long ball against Bowden Francis during the recent Blue Jays vs. Phillies matchup.

Bob File’s baseball journey is a rare case of going from childhood fan to professional player, with the challenge of facing the team he once loved.

His experience speaks to the mental adjustments players must make when reaching the highest level—letting go of childhood fandom, treating every opponent the same, and respecting the game’s unpredictability.

Whether pitching at SkyDome or Citizens Bank Park, File’s career gave him a deep appreciation for both organizations, making him one of the few people who can say he truly understands what it’s like to see both sides of the game.