On what turned out to be the last play of his football career, Doug Flutie bounced the ball off the ground and kicked it through the uprights for the first successful drop kick in the NFL since 1941. It was the culmination of a one-of-a-kind career for a player who should – but probably won’t – be honored with a plaque in the Pro Football Hall of Fame.

Flutie, who announced his retirement yesterday after a 21-year career, spent most of his prime in the Canadian Football League because shortsighted NFL coaches and executives habitually focused on his slight frame instead of his enormous talent. Those years in Canada, where he won six Most Outstanding Player awards, won’t count on Flutie’s Hall of Fame resume because HOF voters, by rule, may only considers accomplishments in American leagues. The likely Hall of Fame snub won’t rankle Flutie, though – he’s used to it by now.

Fans were enamored with Flutie for the same reason NFL coaches were skeptical of him: He looked like an ordinary guy, not a professional football player. Flutie was listed at 5-foot-10, but few who saw him in person believed he was that tall. Despite his size, Flutie had a cannon for an arm, which he first showed the nation in 1984, when he led Boston College (the only major school to recruit him) against the Miami Hurricanes. As any sports fan alive that day will recall, Flutie heaved a 48-yard touchdown pass on the final play of the game to clinch victory for the Eagles as well as the Heisman Trophy for himself. That pass, forever immortalized as the “Hail Mary,” made Flutie a legend but failed to inspire NFL scouts. In the 1985 NFL draft, every team passed on Flutie several times before the Los Angeles Rams finally selected him in the 11th round.

But the NFL had a rival in 1985, which gave Flutie options. Amazingly, one of the few people who believed in Flutie’s potential to be a professional player was Donald Trump, who owned the New Jersey Generals of the United States Football League. Trump, who had already shelled out millions to lure 1982 Heisman winner Herschel Walker to the upstart league, found less resistence in nabbing Flutie. Flutie started immediately and had a good rookie season, passing for 2,109 yards and rushing for 465 more.

When the USFL folded after that season, Flutie was fortunate to find one other person who believed in him: Mike Ditka, coach of the defending Super Bowl champion Chicago Bears, who acquired Flutie in a trade with the Rams. When Bears quarterback Jim McMahon got hurt in 1986, Ditka handed Flutie the starting job for one playoff game. The Bears lost, Flutie took much of the blame, and the following year he left Chicago for his first stint with the Patriots. He spent three seasons there, playing reasonably well for an offense that had little other talent. When the Patriots released him after the 1989 season, no other NFL teams showed any interest.

And so began the most successful portion of Flutie’s career, when he headed north of the border. In eight seasons with the British Columbia Lions, Calgary Stampeders, and Toronto Argonauts, he threw for 41,355 yards and 270 touchdowns and led his teams to three victories in the Grey Cup, the Canadian equivalent of the Super Bowl.

The Canadian field is longer and wider, which gave Flutie more space to do what he does best: improvise. Flutie’s combination of quick feet and great field vision allowed him to see what defenses were doing and react instantly. On some of his greatest plays, neither the opposing defense nor his teammates knew what he was going to do until it was done. Still, overly cautious NFL coaches failed to appreciate Flutie’s improvisational skills.

But Flutie’s accomplishments in Canada did impress the Buffalo Bills enough to sign him in 1998,albeit with the understanding that he would be a backup to Rob Johnson. After the Bills started the season 1-3,though,Flutie inherited the starting job and the Bills went 8-3 with him at the helm. The performance earned Flutie a trip to the Pro Bowl and the chance to enter training camp as the undisputed starter of an NFL team.

That season quickly became a microcosm of Flutie’s career, as his superior performance on the field was overshadowed by a coach’s inability to recognize it. Flutie started the Bills’ first 15 games, sitting out only the season finale against Indianapolis when the Bills had clinched a playoff spot and rested most of their top players. When Johnson started the finale and put up good numbers, coach Wade Phillips benched Flutie and declared that Johnson had earned the starting job for the playoffs. In the Bills’ subsequent first-round loss to Tennessee, Johnson mustered just 131 passing yards, was sacked six times, and fumbled twice while Flutie watched from the sidelines.

Flutie spent one more year in Buffalo (again spending most of his time as Johnson’s backup despite clearly superior play), then signed with the San Diego Chargers in 2001. Flutie turned 39 that season, and his age began to show. After four seasons in San Diego, most of which were spent as a mentor to the young Drew Brees, Flutie signed with the Patriots to finish his career where it had begun, in Boston.

In the history of football, few players have spent as much time in the limelight as Flutie. He burst into the nation’s sports consciousness in 1984, the year most of the players chosen in last month’s NFL draft were born. He was the last former USFL player remaining in the NFL. He spent his last year as the backup to Tom Brady in New England, but he’s closer in age to Terry Bradshaw, who won four Super Bowls with the Pittsburgh Steelers in the 1970s, than he is to Brady, who’s won three titles with the Patriots this decade.

With pro football in his rearview mirror, Flutie, like so many other former players, has agreed to become a college football analyst for ABC and ESPN – the first traditional role for an athlete who never did anything the traditional way.

Mr. Smith is a regular writer for FootballOutsiders.com.