With all the free agent and trade rumors swirling around the internet in the dog days of summer, I decided to compile a list of what I believe are the 5 worst trades in NHL history:

5. November 30, 2005 – San Jose and Boston Bruins

To San Jose: Joe Thornton

To Boston: Marco Sturm, Brad Stuart, Wayne Primeau

Since being dealt to California, Thornton has won both the Art Ross and the Hart Trophy while only Marco Sturm remains on the Bruins roster.  Thornton was the league’s leading scorer in 2006, scoring 92 points with the Sharks that season in just 58 games, and as a Shark, he has had four 85+ point seasons.

4. June 15, 2001 – Ottawa Senators and New York Islanders

To New York: Alexi Yashin

To Ottawa: Zdeno Chara, Bill Muckalt, 1^st Round Pick (Jason Spezza)

For sheer volume, this arguably is one of the worse trades then-Islanders’ G.M. Mike Milbury ever made, and he made quite a few doozies during his reign on the Island. The club moved a future four-time All-Star and 2009 Norris Trophy winner in Chara, as well as the pick that would eventually become Jason Spezza and Muckalt, to Ottawa, for Yashin. He was then immediately signed by Milbury to a 10-year, $87.5 million deal, and in five seasons with the club, saw his numbers steadily decline after an initial 75-point season in 2001-02. Seemingly untradeable, Yashin had his contract brought out by the club in 2007, and he has spent the last three seasons playing in his native Russia.

3. June 20, 1992 – Quebec Nordiques and Philadelphia Flyers

To Philly: Eric Lindros

To Quebec: Peter Forsberg, Ron Hextall, Chris Simon, Mike Ricci, Kerry Huffman, Steve Duchesne, 1^st Round Draft Pick, $15 Million Cash

Quebec drafted one of the most highly touted draft picks of all-time in Eric Lindros only to have him refuse to play for the franchise.  Philly would eventually send an incredible package to Quebec which would help build the foundation for 2 Stanley Cups for the Colorado Avalanche.  Lindros was dominant at times but could never remain healthy enough to lead his team to a Cup Championship of their own.

2. 1967 – Chicago Blackhawks and Boston Bruins

To Boston: Phil Esposito, Ken Hodge, Fred Stansfield

To Chicago: Pit Martin, Gilles Marotte, Jack Norris

Many hockey fans were surprised when Bobby Hull’s centre was shipped off to Boston in 1967, but you could imagine their reaction over the next ten seasons, when Esposito would mature into one of the league’s top scorers. Esposito became the first player in league history to top the 100-point plateau in a season, and then had five more 100-point seasons in a row during the early 1970’s. Esposito became a two-time Hart Trophy winner for league MVP, an icon for the sport, and a future Hall of Famer in 1984. To make matters worse for Chicago fans, Hodge also had two 40+-goal seasons and a 50-goal campaign in 1973-74. Even Stansfield, considered a spare part in this blockbuster deal, had six straight 20+-goal campaigns for Boston from 1967 through 1973.

1. August 9, 1988 – Edmonton and Los Angeles

To Los Angeles: Wayne Gretzky, Marty McSorley, Mike Krushelnyski

To Edmonton: Jimmy Carson, Martin Gelinas, 3 -1^st Round Draft Picks, $15 Million Cash

Oilers management ripped the hearts out of not only Edmonton fans but the whole country when they decided to ship National icon Wayne Gretzky to sunny LA.  The Oilers would go on to win another Cup without Gretz but the legacy of trading the best hockey player ever will always hang over Edmonton’s head.

The silly season has officially begun in the NHL as teams are jockeying for position in this Fridays NHL Draft in Los Angeles and also gearing up for free agency next Thursday.  Many teams will be looking to make a splash leading up to the draft, a la Montreal dealing playoff hero Jaroslav Halak.  This trade will certainly set of a domino-effect of trades and signings in the next few weeks.

There are countless amounts of Mock Drafts being posted all over the internet and here is TSN’s Bob Mckenzie’s. As always, McKenzie provides an outstanding analysis of the potential draft order for this Friday.  Take a look and see who your favorite team might be in the running for.

Once the draft is complete, the heavily anticipated free agency period begins on July 1.  Many, many players will be swopping teams and heading for greener pastures (aka $$) elsewhere.  James Mirtle of the Globe and Mail provides a great list of the Top 100 UFA’s.

So what are you hoping your team does this off-season?  Draft a stud?  Sign a monster free agent?  Stay status quo?  Leave us a comment and let us know what you’re wishing for!