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The 5 biggest NFL flops in Dallas Cowboys history

Drew Henson was one of many failed franchise quarterback prospects that Cowboys fans endured after Troy Aikman's retirement (Photo: Getty)
Drew Henson was one of many failed franchise quarterback prospects that Cowboys fans endured after Troy Aikman's retirement (Photo: Getty)

The Dallas Cowboys are well known for wearing stars on their helmets, a prized emblem worn by several of the most notable names in NFL history. Alas for the storied franchise, not every move they've made has deserved such a designation.

Though the Cowboys have earned five Super Bowl championships, they haven't hoisted the Vince Lombardi Trophy in nearly three decades, a lack of victorious poses brought about by several questionable moves commissioned by owner/general manager Jerry Jones and his management group. SK looks back at the most impactful moves the Cowboys will regret for years to come...

Which moves have set the Cowboys back the most?

One of my favorite Lions highlights. Bobby Carpenter’s pick-six against the Cowboys. Joe Buck’s commentary was completely awful though. https://t.co/d9ppppisEZ

Bobby Carpenter

Dallas history is well known for its "Doomsday Defense," but this defender was purely a doomsday in the annals of Cowboys draft history.

The selection of Carpenter is perhaps the most infamous first-round choice in Cowboys history. He was a personal choice of head coach-turned consultant Bill Parcells during the 2006 NFL Draft, as Big Tuna had previously coached Carpenter's father Rob during their shared period with the New York Giants. The younger Carpenter, however, failed to establish a starting role for himself in Dallas, tallying only 99 tackles and 3.5 sacks over four seasons. Carpenter's most famous football moment indeed came in Dallas...albeit as a member of the Detroit Lions. The linebacker's pick-six of Tony Romo...the only such takeaway of his NFL career...during an October 2011 showdown ignited a Detroit comeback from 24 points down, leading to a Cowboys loss that eventually kept them out of the playoffs. Among those Dallas eschewed in favor of Carpenter were Antonio Cromartie, Tamba Hali, Jonathan Joseph, and DeAngelo Williams.

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