Mine was when the Pittsburgh Penguins lost in overtime in Game 7 to the New York Islanders in the second round of the 1993 playoffs. The Pens had won back to back Stanley Cups and cruised through the '92-'93 regular season, finishing with a 17 game winning streak. They were overwhelming favorites to three-peat.
They crushed the Devils in the first round of the playoffs, but weren't playoff tough when the Islanders unexpectedly played over their heads in the second round. Darius Kasparatis hounded Mario Lemieux mercilessly and the series unexpectedly went to a seventh game. The Pens totally dominated that game, outshooting the Islanders by a 3 to 1 ratio, but backup goalie Glenn Healy stood on his head and New York was ahead with about five minutes left. Ron Francis scored twice in those five minutes to tie the game. In overtime the Penguins again totally dominated play, but the first Islanders shot on goal, a long distance slap shot about six minutes in by a fourth liner named David Volek, sailed over the shoulder of a frozen in place Tom Barasso. That was the worst feeling imaginable.
Second worst -- Sid Bream completing Atlanta's comeback against the Pirates in the ninth inning of Game 7 of the '92 NLCS by scoring on a single by Francisco Cabrera. Bream was probably the slowest runner in baseball, but scored from second because of a terrible throw by none other than Barry Bonds. Bonds will rank as one of the all-time chokers in the playoffs.
Anyone else?
They crushed the Devils in the first round of the playoffs, but weren't playoff tough when the Islanders unexpectedly played over their heads in the second round. Darius Kasparatis hounded Mario Lemieux mercilessly and the series unexpectedly went to a seventh game. The Pens totally dominated that game, outshooting the Islanders by a 3 to 1 ratio, but backup goalie Glenn Healy stood on his head and New York was ahead with about five minutes left. Ron Francis scored twice in those five minutes to tie the game. In overtime the Penguins again totally dominated play, but the first Islanders shot on goal, a long distance slap shot about six minutes in by a fourth liner named David Volek, sailed over the shoulder of a frozen in place Tom Barasso. That was the worst feeling imaginable.
Second worst -- Sid Bream completing Atlanta's comeback against the Pirates in the ninth inning of Game 7 of the '92 NLCS by scoring on a single by Francisco Cabrera. Bream was probably the slowest runner in baseball, but scored from second because of a terrible throw by none other than Barry Bonds. Bonds will rank as one of the all-time chokers in the playoffs.
Anyone else?