I saved the worst for last.
No one player in the history of the NHL has been more responsible for the despair of Caps fans the world over than No. 66 of the Pittsburgh Penguins—Mario Lemieux.
Lemieux and his Penguins met the Capitals in the playoffs a stunning seven times between 1991 and 2001. Lemieux played in five of those series. The Pens, not surprisingly, prevailed in four of those five series.
It was in 1991 when the two teams met in the playoffs for the first time. The Pens easily dispatched the Caps in the Eastern Conference Semifinals in five games en route to their first Stanley Cup.
Lemieux scored two goals and seven assists in that 1991 whitewashing of the Caps.
In 1992, the Penguins would look to repeat as champions. Again, the Caps were there waiting for them. Once again, Lemieux would crush the hopes and dreams of Caps fans.
Things started off really well for the Caps. The Caps won Games 1 and 2 on home ice by a combined score of 9-3. The Pens would finally get on track with a 6-4 win in Game 3 in Pittsburgh. In that game, Lemieux had a hat trick and added three more assists.
But when Dino Ciccarelli scored four goals and the Caps routed the Pens 7-2 in Pittsburgh in Game 4 of the series—along with the Penguins' hopes of repeating as Stanley Cup champions—the series seemed as good as done.
But that is why they play the games.
The Pens beat the Caps 5-2 in Game 5 in Washington and went back to Pittsburgh with momentum. In Game 6, Mario Lemieux would show the world why he was the greatest player in the game at the time as he scored two goals, added three assists and the Pens evened the series with a rousing 6-4 win.
Heading back to Washington for Game 7, the ghosts of past playoff failures weighed heavily on the shoulders of the Caps. Haunted by lingering memories of such collapses as the "Easter Epic" the Caps folded badly under the pressure of another playoff collapse.
Lemieux would score a goal and add an assist and a very young Jaromir Jagr tacked on another goal as the Pens completed the stunning comeback with a 3-1 win in D.C.
The Penguins would go on to repeat as Stanley Cup champions and the Caps were left to try and figure out how things had unraveled so badly, so quickly.
In that 1992 series, Lemieux would end up with a total of seven goals and 10 assists.
In 1994, the Caps would get their only playoff series win over the Pens, eliminating Lemieux and the Pens in six games. Even so, Lemieux did all he could to prevent that from happening as he scored four goals and had three assists in the series.
When the Caps and Pens met in the 1995 playoffs. Lemieux was not there having taken the year off due to exhaustion and side effects that were the result of the radiation treatment he had undergone to treat his Hodgkin's lymphoma.
As such, Lemieux had no part—save for guiding them in spirit—in the Penguins rallying from a 3-1 series deficit against the Caps for the second time in three seasons.
Lemieux was back in 1996, though. The Caps would win the first two games in the Steel City. The Penguins would prevail in D.C. in Game 3 and this set the stage for one of the greatest games in NHL playoff history.
Game 4 of the 1996 Caps vs. Penguins series was an epic in every sense of the word. At the 19:15 mark of the fourth overtime, Petr Nedved would score to end the fifth longest overtime game in NHL playoff history and even the series up.
Game 5 would not be remembered so much for the Pens' 4-1 win but for the series of brawls at the end of the game that saw the Pens' Alek Stojanov leave bloodied while the coaches for both teams nearly engage in a brawl of their own.
In Game 6, goals from Jagr, Ron Francis and Lemieux sealed the deal and the Pens had once again rallied from two games down in the series to defeat the Caps.
In that 1996 series, Lemieux would score two goals but would also add eight assists, four of them in Game 3 alone when the Pens absolutely needed the win.
Lemieux would stick it to the Caps once more in the 2001 playoffs scoring four goals and three assists as the Pens eliminated the Caps in six games. Lemieux was huge in Games 5 and 6.
In Game 5, with the series tied, it was Lemieux's first period goal that turned out to be the game winner.
In Game 6, Lemieux would score the first goal and he would play a key role in the Penguins' 4-3 overtime win that clinched the series.
For those keeping score, in five playoff series between the Capitals and Penguins over a 10 year period, Lemieux scored 19 goals and added 31 assists. He was the Caps' judge, jury and executioner on more occasions than I care to remember.
It would be extremely narrow minded of me, however, to not acknowledge what a great player Super Mario was. And he was one of the most courageous players of all time having endured cancer and several debilitating injuries that would have ended the careers of lesser men.
But when Lemieux finally retired in 2006, the damage he had done to the Washington Capitals franchise was pretty much irreversible.
You can try and argue against it but the evidence is pretty clear—Lemieux is the biggest villain in the history of the Washington Capitals.