5 biggest NHL Trade busts of all time ft. Tuukka Rask to Bruins

Trades are a regular occurrence in the NHL. Whether it's at the draft or at the deadline, some deals end up being wins for both teams, while others look lopsided with hindsight.

In large part, when teams trade prospects and picks, it's hard to know how those players will turn out. As such, sometimes one team gets by far the better of the transaction, which can lead to some embarrassment.

Here are five notable trade busts in NHL history:

#5, Oilers trade Mark Messier

The Edmonton Oilers had Mark Messier as their heart-and-soul player and in 1991 dealt Messier, Jeff Beukeboom, and David Shaw to the New York Rangers for Louie DeBrusk, Steven Rice, and Bernie Nicholls.

Messier had already won five Stanley Cups with the Oilers, and at age 29 he still was one of the best players in the NHL. He ended up leading the Rangers to another Cup in 1994.

As for the return, DeBrusk played parts of six seasons with the Oilers but never was a star. Rice split parts of three seasons between the Oilers and the minors and Nicholls was dealt to the Devils just two years later.

#4, Flames trade Brett Hull

The Calgary Flames no doubt regret trading Brett Hull.

At the age of 23, Hull was in his rookie season and had 50 points through his first 52 career games. However, Calgary decided to deal Hull and Steve Bozek to the St. Louis Blues in exchange for Rob Ramage and Rick Wamsley.

Ramage ended up only playing one season with the Flames, while Wamsley was their backup goalie for four years and was later traded.

Hull, meanwhile, played 11 years with the Blues. In 744 career games played with St. Louis, Hull scored 527 goals and 936 points. He was later inducted into the Hall of Fame.

#3, Islanders deal Zdeno Chara

Zdeno Chara was deal to the Sens

In 2001, the New York Islanders acquired Alexei Yashin from the Ottawa Senators for Zdeno Chara, Bill Muckalt, and a first-round pick.

Yashin was a skilled offensive player but in New York right away his play took a massive dip and he had his contract bought out.

Chara, meanwhile, had 146 points in 299 career games in Ottawa, Muckalt played just one season with the Sens while the first-round pick was used to draft Jason Spezza who had a lengthy career with Ottawa.

#2, Maple Leafs trade away Rask

Tuukka Rask was considered a solid goalie prospect but was still years away from the NHL.

In 2006, Toronto Maple Leafs needed an NHL-ready goalie and dealt Rask to the Boston Bruins for Andrew Raycroft. Raycroft played just two seasons and had his contract bought out.

Rask, meanwhile, played his entire 15-year NHL career with the Bruins and went 308-165-66 with a 2.28 GAA and a .921 SV%. He also led Boston to the Stanley Cup in 2011. It goes down as one of the worst trades of all time.

#1, Oilers trade Gretzky

Arguably the worst trade in NHL history was the Edmonton Oilers dealing Wayne Gretzky to the Los Angeles Kings.

At the time, Gretzky was the most dominant player in the NHL. In 1988, while he was 26, he was dealt to the Los Angeles Kings. Gretzky continued his dominance as a King while the Oilers didn't get much in return.

Edmonton traded Gretzky, Marty McSorley, and Mike Krushelnyski for Jimmy Carson, Martin Gelinas, and first-round picks in 1989, 1991, and 1993 along with $15 million in cash.

Carson did post a 100-point season but only was with Edmonton for two years, and Gelinas didn't accomplish much. With the picks, Jason Miller played only six games, Nick Stajduahr played only two games and Martin Rucinsky only played two games with Edmonton, but was a solid NHL player.

Trading the best player in the NHL usually results in a loss but the return was disappointing for the Oilers.