Jaromir Jagr
2001: 7 years, $77 million ($11m per)
After acquiring the dynamic scoring winger from the Penguins in 2001, the Capitals signed him to an extension -- the largest contract in the NHL at the time -- that they ultimately lived to regret. When Jagr underperformed (the Caps made the playoffs once during his tenure) and created friction in the dressing room, they traded him to the Rangers in January 2004 and were stuck paying between $4 million and $4.5 million on each of the deal's remaining years.






