In June 1995, a Major League Baseball team used an 18th-round draft pick on a left-handed-hitting catcher from California. That catcher had a football scholarship waiting and never played a single professional baseball game. He went on to win seven Super Bowls instead.

The Scout Who Found Him

John Hughes, an Expos scout, had spent time watching Tom Brady play at Junipero Serra High School in San Mateo, California. Brady had moved from first baseman to catcher his senior year and hit .311 with eight home runs. Hughes rated Brady a genuine pro prospect - on talent alone, a late second-round pick. But the Expos placed Brady in the 18th round for one clear reason: everyone in baseball knew he had committed to the University of Michigan on a football scholarship and would be nearly impossible to sign.

What the Expos Saw

Hughes described Brady as already standing around 6-foot-3 with a strong athletic frame, the arm strength catchers need behind the plate, pull-side power, and a sharp instinct for the game. Expos general manager Kevin Malone went further, later saying Brady "could have been one of the greatest catchers ever." Hughes reflected on the failed recruitment with a line that captures just how unusual the situation was: "I never had as much fun scouting a player that we eventually didn't sign."

Brady Chose Football

Brady enrolled at Michigan, competed hard for a starting role, and eventually became one of the most decorated quarterbacks in college football history. The New England Patriots selected him in the sixth round of the 2000 NFL Draft - 199th overall, a pick that became one of the most famous in league history. What followed: seven Super Bowl titles, five Super Bowl MVP awards, and a near-universal consensus as the greatest quarterback who ever played.

His Take on the Road Not Taken

When asked what his life would look like had he chosen baseball, Brady was direct: "I'd be selling insurance, man. Baseball was not my sport." When Brady retired from the NFL in February 2023, a small footnote attached to the announcement - he became the last active professional athlete drafted by the Montreal Expos, a franchise that had folded nearly two decades earlier.

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