The 5 biggest NFL flops in Dallas Cowboys history

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?

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.

Taco Charlton

In the opening round of the 2017 draft, the Cowboys believed that the next great sack master lingered toward the end of the first round. They were right...but missed him by two picks.

Shortly before T.J. Watt went to the Pittsburgh Steelers with the 30th pick, Dallas used No. 28 on his fellow Big Ten rep Taco Charlton. What Charlton failed to put up in the box score he made up in personality, notably playing his nickname and preparing imaginative tacos for his teammates after big plays. Alas, few of those plays came from Charlton himself, who struggled to carve a role for himself on the Dallas defensive line. Inefectiveness and injuries limited him to a mere 18 games in blue and white and he was eventually released at the start of his third season with the team in 2019. Charlton has since spent the past three years with three different teams, most recently joining the Pittsburgh Steelers.

Galloway, seen in 2003, was productive, but not enough to justify the massive price the Cowboys paid for him (Photo: Getty)

Joey Galloway

Often labeled one of the greatest players who never participated in a Pro Bowl, Galloway made a name for himself with three 1,000-yard seasons over his first four years in Seattle. With Troy Aikman and Michael Irvin on their respective ways out, the Cowboys needed to upgrade their offensive weaponry and eventually dealt their first premier picks of the century to the Seahawks in exchange for Galloway's services.

While mostly effective, especially considering the hodgepodge of quarterback infamy Galloway had to work with (more on that in a minute), the receiver never truly justified the seven-year, $42 million deal he was bestowed at the onset of his Dallas tenure. He tore his ACL in his Dallas debut and never reached 1,000 yards in four seasons in Texas (he was traded to Tampa Bay in 2004 for an aging Keyshawn Johnson). Not only did the massive contract hamper the Cowboys' free agency efforts, the ultimate insult came when the Seahawks used those first-round picks to draft Shaun Alexander and Koren Robinson, each of whom became major contributors toward a Super Bowl run in 2006.

Drew Henson

The Cowboys' history can be defined by different quarterbacks, each of whom oversaw varying degrees of success in each decade: Don Meredith in the 60s, Roger Staubach in 70s, Danny White in the 80s, Troy Aikman in the 90s, and Tony Romo in the late 2000s/early 2010s. Dak Prescott took over in 2016 and appears well on pace to rule the 2020s. But the period between Aikman and Romo is a gridiron netherworld of horrifying proportions, as the turn of the century saw several potential franchise saviors falter under the Dallas pressure...everything's bigger in Texas, after all.

The most notable of these follies was Henson, who previously engaged in the publicized battle for playing time with Tom Brady at the University of Michigan before embarking on a baseball career. After a brief eight-game stint with the New York Yankees, Henson was acquired by Dallas in 2004, part of a bizarre trend where the Cowboys turned to former baseball players to find the answer at quarterback (his predecessors included Quincy Carter and Chad Hutchinson, who respectively spent time with the Chicago Cubs and St. Louis Cardinals). Henson was seen as a potential franchise man after the Cowboys opted to use Vinny Testaverde as a stopgap quarterback during the 2004 season, but he was granted the starting duties for the annual Thanksgiving game against Chicago. Alas, things didn't go well as Henson completed only 4-of-12 passes for 31 yards an interception returned for a touchdown, leading Parcells to go back to Testaverde. Romo's ensuing rise made Henson expendable and he went on to throw only two more passes in his NFL career (both coming with Detroit in 2008).

Williams (11) seen in 2008 (Photo: Getty)

Roy Williams

The name "Roy Williams" offers conflicting emotions for Cowboys fans, especially those of the millennial variety. If it's the safety Roy Williams you're referring to, it'll likely bring smiles to their faces. Alas, receiver Roy Williams is another story.

For four seasons, Williams was one of the rare silver linings of new century Detroit Lions football. Dallas often inquired about his services as the team sank deeper into gridiron oblivion and finally managed to bring the Texas alum home through a 2008 deal that sent three draft picks (including the Cowboys' first-rounder in 2009) to the Motor City. Williams himself was bestowed a new six-year, $54 million contract in the process as well. He never earned more than 600 yards in three seasons with the Cowboys, losing snaps to young breakout talents like Miles Austin and Dez Bryant. He was released after three of the six seasons of his contract during the summer of 2011.