NHL Free Agency: 10 Infamous Chicago Blackhawks' Deals Throughout the Years

The Chicago Blackhawks haven't had the best track record in free agency, especially when they open up the vault.

Blackhawks' history is rile with cautionary tales.  Big news and big money have led to some wild rides for the 'Hawks in the free agent market.

Here are ten memorable signings over the years.  Each bears another look for the way they turned out for Chicago.

Bobby Orr, 1977

When you sign one of hockey's all-time greats, it can only be a positive, even if he was injured for most of the season before.  Right?

Orr, only 28 and a season removed from a 135-point 1974-75 campaign with the Bruins, was signed to a five-year, $3 million deal by Chicago.  Unfortunately, the defenseman played in just 26 games for the 'Hawks over the next three seasons before hanging it up for good in 1979.

Bob Probert, 1994

Those fans still smarting from the signing of Daniel Carcillo would do well to remember when the 'Hawks signed the wild man from Detroit to a four-year, $6.6 million contract.

This was one of the Red Wings most dangerous weapons.  A guy who would net a key goal and then knock your block off.  'Hawks fans spent many nights cursing Probie, who opened up his Chicago tenure by missing his first season with problems stemming from his notorious struggles with drugs and alcohol.

Probert returned to the NHL in 1995-96 and had a 40-point season, though his production dropped dramatically over the next few years.  While he rarely the player he was in Detroit, he won a lot of fans over in Chicago. 

Doug Gilmour, 1998

Apparently, Chicago's plan was to sign Gilmour along with Brett Hull that summer.

Instead, it was just Gilmour, for three years and $6 million.

At age 35, the recent Hall of Fame selection had a decent year and was named captain when Chris Chelios left town.  However, he suffered a back injury late in the 1998-99 season, and the following spring he was dealt to Buffalo.

Wendel Clark, 1999

If you blinked, you missed Clark's time in Chicago.

Clark was an All-Star for the Lightning in 1998-99 before finishing the season with Detroit.  Bob Murray signed him to a one-year, $1.4 million contract, which was bought out after Clark scored two goals in 13 games.

Theo Fleury, 2002

This train wreck was all the more memorable in that the 'Hawks had to see it coming all the way and still signed Fleury to a two-year, $8.5 million deal.  They even had to compensate San Jose, who had his rights,  with a draft pick.

Despite this, GM Mike Smith couldn't get Fleury's name on a contract fast enough despite a host of substance abuse issues. 

Fleury rewarded Chicago's roll of the dice by being suspended via the NHL substance abuse policy for the first two months of the 2002-03 season.  He returned in time for an altercation at a Columbus strip club in January of 2003.

The 'Hawks waived Fleury, but there were no takers.  After the season, Fluery was suspended by the league again and was through in the NHL. Smith lost his job thanks in part to this debacle.

The most unbelievable part of this story was how Smith threw big money Fleury's way even in the face of all the red flags.  If you haven't read Fleury's book, it's worth a look to understand how Fleury's demons controlled him for most of his NHL days and the circumstances leading up to his signing with Chicago.

Nikolai Khabibulin, 2005

Dale Tallon loves to spend money.  In theory, signing Khabibulin, who had just won a cup before the NHL lockout with Tampa Bay, was a good move.  Tallon's four-year $27 million deal set the bar pretty high.

Too high, as it turned out.

Inconsistency and injury were Khabibulin's calling cards in the Indian head sweater.  Posting a 3.35 GAA in his first season between the pipes doomed him to intense scrutiny for the rest of his time in Chicago.  Only Tallon's signing of an inferior goalie three seasons later took some of the heat off.

It's fitting that the Bulin Wall was down and out in his final games with the team, as an injury took him out of the 'Hawks loss to Detroit in the 2009 Western Conference Finals.

Adrian Aucoin, 2005

Tallon also foreshadowed big contracts for defensemen when he signed Aucoin to a four-year, $16  million deal.

Aucoin was enough of a leader to be a captain in his two years with Chicago, but his groin kept him from being effective on the ice.  He missed 39 games over his two years in the Indian sweater with the injury.

In 2005-06, he also underwent shoulder surgery and missed the last 31 games.

In the two seasons before signing with the 'Hawks, Aucoin tallied 35 and 44 points.  In the two season after the 'Hawks dumped his contract on Calgary, he scored 35 and 34 points.  He missed 17 games combined in those four seasons.

Aucoin's combined numbers in Chicago for the two years he was here?  Five goals, 17 assists, 22 points.  He played in 92 of a possible 164 games.  For the money Tallon shelled out, this is arguably the worst signing the 'Hawks ever made.

Brian Campbell, 2008

Tallon's biggest contract with the 'Hawks can in the form of the eight-year deal worth $56.8 million given to Campbell.  The cries of the contract being an albatross began the next day.

Campbell was a good player and veteran leader on Chicago.  He helped bring the Stanley Cup to town in 2010, but his enormous salary was never far from our minds. 

If you compare Campbell's three seasons in Chicago to Aucoin's tenure here, the 'Hawks received a far more productive and healthy player in Campbell.  He played well when he was here and was missed when he was out of the line up.  He also worked hard to work himself into the Chicago community.

The fact that the last five years of the deal will be paid by Florida makes it easier to swallow historically for 'Hawks fans.  Especially considering Tallon's other big signing that summer.

Cristobal Huet, 2008

Without even waiting for Khabibulin's monster deal to run it's course, Tallon inked the 34-year-old Canadiens goalie for four years and $22.5 million.

Huet then managed to make the fans start pulling for Khabibulin in the 2008-09 season, then for Antti Niemi the following year.  He never earned the confidence of fans or, more importantly, coach Joel Quenneville.

Huet has likely played his last game with Chicago, having been loaned out to a Swiss team last season.  Unless someone is willing to trade for him this summer (you listening, Dale Tallon?), Chicago will eat over $10 million on this deal just to keep Huet off the United Center ice.

Marty Turco, 2010

Turco wasn't the high-priced gaffe that the Khabibulin and Huet signings turned out to be, but he was another veteran who didn't work out in Chicago.

This deal blew up in Stan Bowman's face when he was forced to let Antti Niemi walk following his helping the 'Hawks to a championship.  Turco was supposed to solidify the 'Hawks in net until Corey Crawford could mature into the starter. 

However, the team chose to make a change when Crawford rapidly became the team's best option between the pipes.

Turco handled an awkward situation with class, but having his Degree commercial air repeatedly in games in which he was also a spectator could not have been more embarrassing.

Ten contracts that went awry in one way or another.  Which of these signings turned out the worst for Chicago in your opinion?