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Did the man in fleece fleece himself on purpose?

This past weekend marked the beginning of the NFL free agent season and also featured the league's first blockbuster trade of the year. With Tom Brady set to return from his knee injury, the New England Patriots sent his replacement, Matt Cassel, as well as longtime linebacker Mike Vrabel to the Kansas City Chiefs for their 2nd round pick in this year's draft.

There are all kinds of arcane and not-so-arcane salary cap reasons that Pats coach Bill Belichick made the trade, but anyway you slice it, he gave up a lot more than he got, a fact made all the more juicy for conspiracy-minded fans by current Chiefs general manager Scott Pioli's former gig as New England's vp of player personnel (a.k.a. Belichick's co-architect in the making of the Pats' dynasty). At the very least, the whole thing doesn't pass an initial sniff test, but it's not the first iffy transaction, as you'll see in Complex's list of the 5 Shadiest Deals in Sports History.

#5. 1920: THE BOSTON RED SOX CURSE THEMSELVES
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• The 1920 swap of Ruth for a bucket of cash is the most famous, but between 1918 and 1923 the Sox and Yanks made more than half a dozen trades, most involving players moving to New York and various amounts of greenbacks heading to Beantown. The Sox had an owner who preferred producing Broadway plays to producing winning baseball teams and as a result, Boston went from a club that won the World Series in 1918 to one that averaged 100 losses for eight seasons, gifting their arch rivals plenty of ammo for their run of dominance along the way.

#4. 1988: "NO, CANADA"
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• Whether he jumped or was pushed, the '88 deal that sent the greatest hockey player of all time from the Edmonton Oilers to the L.A. Kings for $15 million in cash and a bunch of draft picks was undoubtedly one of the most dubious in the history of professional sports. Kinda like the Christians trading Jesus to Hindus for a bunch of good karma.

#3. 2008: THE GRIZZLIES HAND THE LAKERS THE WESTERN CONFERENCE TITLE
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• Pretty much every trade in the NBA qualifies as shady these days, but the exchange of the All-Star Pau Gasol for a couple draft picks and a bunch of not even spare parts (Kwame Brown!) was one that arguably handed the Lakers a ticket to the Finals last year. Of course L.A. couldn't seal the deal in June because of the next entry on our list.

#2. 2007: KEVIN MCHALE GIVES DANNY AINGE AN ASSIST
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• Yeah Kevin Garnett was sick of being in Minny and yeah, the T'wolves got Al Jefferson, but you've gotta be wicked naive to think there wasn't a little wink-wink nudge-nudge when McHale shipped KG to his former teammate Danny Ainge. McHale saved Ainge's job; in return, he probably signed his own pink slip.

#1. YESTERDAY: THE OWNER OF A TEAM NAMED "A-ROID FOR LIFE" DESTROYS THE INTEGRITY OF FANTASY BASEBALL
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• Hypothetical situation: you've got an old fraternity brother who goes and marries a real turd of a blond bimbo, then invites said bimbo to join your longtime fantasy baseball league, whereupon blond bimbo takes Albert Pujols with the first pick in the draft and promptly trades him to her hubby for BARRY FRICKIN' ZITO because BZ is "dreamy." Not-so-hypothetical response: Steve, you're no longer in the wedding party and we want that stupid china tea set we bought you and Michelle back.