21. Larry Walker

The rise of Larry Walker in Montreal remains one of the most brilliant chapters in the franchise's home-grown development. Discovered at a national training camp in Saskatchewan, the Maple Ridge, British Columbia, native was famously signed as an unheralded amateur free agent for a microscopic $1,500 bonus. Initially a raw athlete who had prioritized ice hockey for most of his youth, Walker underwent an extraordinary physical and technical transformation in the minor leagues. By the dawn of the 1990s, he had emerged as the gold standard for a true five-tool player, turning right field at Stade Olympique into his own highlight reel.

His early full seasons established him as a key foundational player in a rising, legendary Expos core. Walker combined broad athletic ability with a quick, aggressive left-handed swing. In a remarkable 1992 breakthrough, he overwhelmed National League pitching by hitting .301 with 23 home runs, earning his first Gold Glove and Silver Slugger awards, and becoming the only Canadian-born player to be named Expos Player of the Year. He maintained that high standard effortlessly in 1993, earning another All-Star selection and a second Gold Glove, solidifying his reputation as a globally recognized superstar.

Walker's remarkable 1994 schedule stands out as his top individual achievement in Canada. Despite suffering a severe rotator cuff injury that limited him to first base to safeguard his shoulder, his offensive performance remained exceptional. He batted an impressive .322 and led all of Major League Baseball with 44 doubles, providing a crucial role for a outstanding Montreal team that held the best record in baseball before the strike interrupted play.

Yet, within the organization’s broader historical ledger, the conclusion of his tenure remains one of the most painful "what-if" scenarios in sports history. Unlike a traditional trade market, the small-market franchise collapsed under financial constraints after the lockout. Desperate to slash payroll, the front office declined to offer arbitration to their superstar right fielder, which granted him free agency a year early. In April 1995, Walker took his final walk away from Quebec, signing a lucrative contract with the Colorado Rockies, where he would later capture a landslide National League MVP Award and three batting titles on his path to Cooperstown.

Walker, with Montreal, amassed 666 hits, 140 doubles, 14 triples, 99 home runs, and 384 RBIs. Using his elite speed, he stole 76 bases and posted a .281/.357/483 slash line—128 OPS+. He was inducted into the Canadian Baseball Hall of Fame in 2009 and the National Baseball Hall of Fame in Cooperstown as part of the Class of 2020.