The 5 biggest NFL flops in Dallas Cowboys history

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.