By Ian Harrisoon
Sportsnet Staff

The silliest shopping season of the year is about to begin, and we're not talking about the Christmas rush at your local mall. Baseball's free agent frenzy kicks off today, with millions of dollars sure to be splashed on talent, some proven and some more questionable. So before general managers squeeze all those extra zeros into the company chequebook, perhaps they should take a step back and ask an important question: Could this colossal contract ever wind up on The List of Free Agent Failures?

Derek Bell: Any free agent signing that ends with the player going into 'Operation Shutdown' must be considered a failure. That was the end result of Pittsburgh's putrid deal with former Jays outfielder Derek Bell, who left the team to live on his yacht following a feud with management in spring 2002, one year after he hit a horrid .173 with five homers and a measly 13 RBIs in the first season of a two-year worth almost $10 million. Parting ways with Bell cost the team $4.5 million, leading one local writer to dub him "the ultimate Pirate: lives on a boat and steals money."

Kei Igawa: Five years after the Yankees paid $26 million to negotiate with him, and another $20 million to secure his services for five years, Kei Igawa was still in pinstripes last summer. The only problem: they were the pinstripes of the Double-A Trenton Thunder. A huge star in his native Japan, where he captured a trio of strikeout titles, Igawa won just two games for New York over the course of his contract. Yankees GM Brian Cashman called him "a disaster."

Vernon Wells: When he signed Vernon Wells to a seven-year, $126 million dollar extension in 2007, former Jays GM JP Ricciardi hoped he was getting the Rolls Royce of outfielders. Turns out, all he got was a VW. Hampered by injuries, Wells was serviceable but far from spectacular after signing the back-loaded deal. Many Blue Jays fans considered it a masterstroke when new GM Alex Anthopoulos found a taker for this albatross deal, trading Wells to the Angels last winter, leaving them on the hook for four years and over $80 million.

Barry Zito: Seven years and $126 million was the same sum the San Francisco Giants used to tempt left-hander Barry Zito across the bay from Oakland in 2007, the largest contract ever given to a pitcher at the time. Zito hasn't even come close to living up to that lofty deal, failing to record a winning record or an ERA under 4.00 in any of his five seasons. Even worse, the Giants left their high-priced lefty off the post-season roster during 2010's run to the World Series title.

Manny Ramirez: Not one, but two different teams can arguably claim than Manny Ramirez was the worst free agent signing in club history. The Dodgers gave Ramirez $45 million over two years in 1999, only for Manny to miss 50 games after testing positive for a banned substance. LA placed the mercurial Manny on waivers in the midst of a mediocre and injury-riddled 2010 season, and happily handed him off to the White Sox. Tampa Bay didn't risk much cash on Ramirez with a $2 million, one-year deal for 2011, but Manny was gone after only five games when he tested positive again, choosing retirement over a 100 game suspension.

Mo Vaughn: He was a perennial All-Star with the Red Sox, even an AL MVP winner. But when Mo Vaughn bolted Boston for a six-year, $80 million deal with the Angels, it's safe to say he didn't get off on the right foot. In his very first game in 1999, Vaughn injured his ankle when he fell down the dugout steps chasing a pop fly. He recovered to put up two solid seasons, but missed all of 2001 with a torn biceps muscle before being traded to the Mets. With Vaughn gone, the Angels would win the World Series the very next year.

Gary Matthews Jr.: What is it with the Angels and awful contracts? Outfielder Gary Matthews Jr. also benefitted from Anaheim's largesse, signing a five-year, $50 million deal with the Halos after posting career highs in average (.313), homers (19) and RBIs (79) with Texas in 2006. But Little Sarge, son of the former Jays hitting coach, was busted back to private during three so-so years in SoCal before he was finally traded to the Mets, with Anaheim forking out $21 million just to get rid of him.

Albert Belle: It wasn't so much an absence of production as a complete absence of personality that made slugger Albert Belle so unpopular signing after he inked a five-year, $65 deal with Baltimore in 1999. Belle bashed 60 homers and drove in 220 runs in two seasons with the O's, but proved to be a total zero in an already toxic clubhouse, making lewd gestures to fans and launching a player protest against an exhibition game with Baltimore's Triple-A affiliate. Then, almost mercifully, he was gone, forced to retire because of a degenerative hip condition.

Mike Hampton: He was a 22-game winner while pitching at sea level in Houston, but lefty Mike Hampton's stats shot sky high when he moved to the rarefied Rocky Mountain air of Denver in 2001. Hampton's eight-year, $121 million deal was the biggest in sports history at the time, and it became one of the biggest blunders. After going 14-13 with a 5.41 ERA in his first year, he slumped to 7-15 with an ugly 6.15 ERA the following season. Traded to Florida and then Atlanta, Hampton missed all of 2006 and 2007 with elbow injuries, and averaged just seven wins per season over the life of his contract.

Denny Neagle: Hampton was horrible at high altitude, but Denver discovered an even bigger dolt in Denny Neagle. Signed the same winter as Hampton to a five year, $51 million deal, the lefty went19-23 with a 5.57 ERA in parts of three seasons. Sidelined by arm injuries, he was cut in 2004 after being arrested for soliciting oral sex. Colorado cited a morals clause in Neagle's contract and got $3.5 million back, but still paid him about $16 million to simply go away.