Who’s on the Mount Rushmore of most hated figures in Dallas Cowboys history?

Roy Williams, Former Cowboys Wide Receiver

For two years, the Cowboys tried to land Roy Williams, as Jerry Jones had his heart set on acquiring the former Texas standout. The Detroit Lions, however, were reluctant to make a move — that is, until Williams was ready for a new contract.

That’s when they sent him to the Cowboys and Jones sent the Lions the farm. In exchange for Williams, Dallas surrendered a first, third, and sixth-round draft pick. They then agreed to a six-year, $54 million extension with $26 million guaranteed. That might not sound terrible in today’s market, but it was one of the richest deals for a wideout at the time.

Williams then joined a receiving corps that included Terrell Owens, Patrick Crayton, and tight end Jason Witten. In 10 games during that 2008 campaign, Williams managed just 19 receptions for 198 yards and a touchdown.

The front office convinced themselves he just needed a full offseason in their system to get back on track, and made him the No. 1 wideout when they released Owens ahead of the 2009 campaign. Thankfully, Miles Austin broke out with 81 receptions and 1,320 yards, because Williams wasn’t up to the task.

That year, he finished with 38 catches for 596 yards. The following season was similar, with just 37 receptions for 530 yards. He was also guilty of several drops and had a crucial fumble on Thanksgiving Day against New Orleans in 2010. Williams had originally caught a pass that looked to seal a win for Dallas, but wound up fumbling the ball away, and the Saints scored the winning touchdown on that possession.

After just 40 games, Williams was released and has gone down as one of the biggest failed trades in league history.