What do you say for those players who came so close to a Stanley Cup championship, only to have lost? Even harder, what can you say for those players who came so close, only to lost three, four, even five times?! Few would know better what it feels like to lose in the Stanley Cup Finals than 15-year NHL veteran and 1,000-point scorer Brian Propp. After all, Brian Propp made it to the championship round FIVE times in his career, and each time came up short.

The 14th-overall pick in the 1979 NHL draft, Brian Propp made it to the Stanley Cup Finals in his rookie season as a member of the Philadelphia Flyers. Propp played in all 80-regular season games for the Flyers that year, as well as all 19-playoff games. As a rookie, Propp finished third overall in team scoring with 75-points (34-goals, 41-assists) during the regular season, and tallied another 15 (5-goals, 10-assists) during Philly’s run to the Finals. The Flyers were laden with high-energy youngsters like Propp that season, but would fall to the New York Islanders in six games in the Stanley Cup Finals; it would be the first of four consecutive championships for New York.

Certainly not a bad set of circumstances at the time for Propp. Making it to the Finals in only his rookie season, most youngsters might take the experience for granted and think that achieving a Stanley Cup championship might be easier than expected and happen with some regularity. But for Brian Propp it would not be the case. Propp would make it all the way to the Finals round two more times as a Philadelphia Flyer; once again in 1985 when they would be backstopped by the late Swedish goaltending phenom Pelle Lindbergh, and then in a 1987 seven-game heart breaker in which their own goaltender, Ron Hextall, would win the Conn Smythe Trophy as the most valuable player in the playoffs, despite being the losing netminder. Both Finals losses coming at the hands of the Wayne Gretzky-led Edmonton Oilers dynasty.

I suppose in some ways for Propp it may have felt like three-strikes and out. Propp would move on from the Philadelphia Flyers via a mid-season trade with the Boston Bruins in March of 1990 for a 2nd-round draft pick. In less than a season with his new team, Propp would find “immediate” success once again, as the Bruins, backstopped by the eventual Jennings Trophy winning goaltending tandem of Andy Moog and Rejean Lemelin, and the eventual Norris Trophy winning defenseman Ray Bourque, would make it to the Stanley Cup Finals; a fourth time for Brian Propp. In 20-playoff games, Propp would chip in 4-goals and 9-assists. For a fourth time though, it was all for naught – Boston would be knocked off in 5-games by the Edmonton Oilers who would win their fifth Stanley Cup. The 5-game series was extremely lopsided with Propp’s Bruins mustering a mere 8-goals in the series while Edmonton exploded for 20. Propp himself would go pointless in the series.

Propp’s fifth and final shot at a Stanley Cup ring would be right around the corner. The following season, his first as a member of the Minnesota North Stars, Propp finished third in team scoring during the regular season by tallying 26-goals and 47-assists in 79-games. Of the 16-teams that qualified for the playoffs in the 1990-91 season, the North Stars finished 15th and went on a Cindrella-esque run. Averaging a point per game during the playoffs (23-games, 8-goals, 15-assists, 23-points), Propp was one of the driving forces behind Minnesota’s improbable run. And despite a strong level of experience from other veterans like Bobby Smith, Neal Broten, Stew Gavin, and Curt Giles, the North Stars would prove no match for Mario Lemieux’s Pittsburgh Penguins who would claim the Stanley Cup in Minnesota during Game Six.

Brian Propp certainly played his heart out to win the Stanley Cup; he just came up short. If you add up the totals of the five Finals series that Propp played in you can certainly appreciate the effort, at the very least. Propp played in a total of 29 Stanley Cup Finals games, and recording 10-goals and 12-assists for 22-points. His best effort would be the 1987 Finals series, when Brian led the Philadelphia Flyers in scoring for the Finals with 9-points (4-goals, 5-assists) in 7-games.

In one’s own heart and mind, how can it be resolved to come so close on five separate occasions only to come up short? If I was in Brian Propp’s shoes I may have a difficult time reconciling this with myself. But Propp also had a very successful NHL career. In over 1,000 regular season games, he averaged nearly a point per game; 1,004-points in 1,016-games. Propp played in the NHL All-Star Game in 1980, 1982, 1984, 1986 and 1990. Propp also holds the NHL records for most career playoff power play goals, most career playoff assists, and most career playoff points all by a left-winger. Those are all noteworthy accomplishments in a lengthy career.

While he never got to raise the Stanley Cup, nor was his name ever inscribed for permanent display, it would be tough to say that Brian Propp did not have a superb career. I think of the Buffalo Bills losing four straight Super Bowls in a row. At the time, it is heartbreaking if not downright embarrassing. But as the years pass and more time to reflect has gone by, to make it to a championship series five times is remarkable for any athlete, in any sport, win or lose. Brian Propp, you were one of the elite competitors of your sport.