The Caps would make the playoffs for each of the next 14 years in a row, but every time it ended in heartbreak. In the late 1980s, the Capitals, always a contender in the regular season, could never shake off its reputation for being "chokers". Despite a continuous march of stars like Gartner, Carpenter, Mike Ridley, Dave Christian, Dino Ciccarelli, Rod Langway or Kevin Hatcher, only once in that time period did the team ever get past the second round of the playoffs, a 4-game sweep at the hands of the Boston Bruins in the 1990 Wales Conference Finals.
By the mid-1990s, the Capitals seemed to fritter away whatever chance at lifting the Stanley Cup. Despite having rising stars in right-winger Peter Bondra, defenseman Sergei Gonchar and centre Joe Juneau (the latter already having his best days behind him when he was traded from the Bruins in 1994), the team's core players were mostly aging. One of the team's darkest days came in a 1993 playoff series with the New York Islanders, when Dale Hunter was suspended 21 games for a vicious hit on Pierre Turgeon after he had just scored the series-winning goal.
The Capitals finally took a step to getting rid of their choker image in 1998. Peter Bondra's 52 goals led the team, veterans Juneau and Adam Oates returned to old form, and Olaf Kolzig had a solid .920 save percentage as the Caps got past the Bruins, Ottawa Senators and Buffalo Sabres (the latter on a dramatic double-overtime win in game 6) en route to the team's first (and to date, only) Stanley Cup finals appearance. However, the team was no match for the juggernaut Detroit Red Wings, who won in an easy four-game sweep.
The Caps returned to form in 1999, losing their spark from the previous year and missing the playoffs. After two more lackluster years (both ending in first-round playoff defeats to the Pittsburgh Penguins), the Caps scored a major coup in the summer of 2001, landing Jaromir Jagr, one of the best players in the NHL in the 1990s, for a song from a near-bankrupt Pittsburgh team. Despite the new power, the Caps failed to make the playoffs in 2002.
The Caps were back in the playoffs in 2003, but disappointed fans again by losing in six games to the Tampa Bay Lightning after starting off with a two-game lead in the best-of-seven first-round series.