The 8 Best & 7 Worst Dallas Cowboys Of The 21st Century

Dallas rosters have been filled with all kinds of talent throughout the first two decades of the 21st century.

The Dallas Cowboys are one of the most storied franchises in the history of the National Football League. Dallas won five Super Bowl titles between 1971 and February 1996, a feat that has only been matched by the New England Patriots, San Francisco 49ers and the Pittsburgh Steelers, the last of which possesses six Vince Lombardi Trophies. With that said, it has been over two decades since the Cowboys last won a conference title, and “America’s Team” recently suffered a harsh home playoff loss to the Green Bay Packers in January 2017. It’s possible, considering how quickly things can go poorly for franchises and for NFL players, Dallas will never again have as good an opportunity to win a Super Bowl before the end of the decade.

Dallas rosters have been filled with all kinds of talent throughout the first two decades of the 21st century. Truth be told, at least a few players who have suited up for the Cowboys over that time should be inducted into the Hall of Fame in the future. Executives running the Cowboys, most notably club owner, president and general manager Jerry Jones, have often failed to surround great players with foundations needed for championship sides, and, thus, the franchise has wasted some special careers during the current century. The best example of this is the team’s greatest ever regular season quarterback, a man who seems destined to retire without ever winning a single ring and with a reputation for being unable to win on football’s biggest stages.

15 Best: Travis Frederick

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The current offensive line of the Cowboys has, for several seasons, been a dominant force and arguably the best line of the current century. Thus, we begin with Travis Frederick, the center Dallas selected late in the first round of the 2013 NFL Draft. Frederick is quickly becoming a mainstay on Pro Bowl rosters, and he was a first-team All-Pro in 2016.

14 Worst: Dwayne Goodrich


The Cowboys selected defensive back Dwayne Goodrich with the 49th pick of the 2000 NFL Draft, and that proved to be only the beginning of an experiment that never worked out for the club. Goodrich dealt with injuries before ever taking the field for a meaningful regular season game, and he made only one start across two seasons according to Pro-Football-Reference.

13 Best: Tyron Smith

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We turn our focus to another Dallas offensive lineman. The Cowboys acquired Tyron Smith with the ninth pick of the 2011 NFL Draft, and the left tackle has proven to be worth that value and even more while protecting the blind sides of quarterbacks such as Tony Romo and Dak Prescott.

12 Worst: Randy Gregory

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It remains difficult to adequately rate Randy Gregory because so much is unknown about the defensive end’s NFL career. Dallas selected Gregory in the second round of the 2015 NFL Draft, and he experienced an up-and-down rookie campaign, during which he managed to flash some moments of brilliance and promise.

11 Best: Dez Bryant

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Dez Bryant may anger some Dallas fans and even analysts with his antics on the field and on sidelines during games, but nobody can deny the 28-year-old is one of the most talented and gifted wide receivers in the NFL today. Bryant has been named to three Pro Bowl squads during his young career, and he led the league in touchdown catches (14) for the 2014 campaign.

10 Worst: Ebenezer Ekuban


When the Dallas Cowboys spent a first-round pick on Ebenezer Ekuban back in 1999, the club probably hoped to be acquiring a defensive end capable of dominating offensive lines and getting to quarterbacks via his athleticism and speed. Instead, Ekuban is now remembered as being one of several failed pass-rushed drafted by the Cowboys over the past 20 years.

9 Best: La'Roi Glover

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It’s possible La'Roi Glover is the best free-agency signing made by the Cowboys this century. The defensive tackle began making Pro Bowl squads as a member of the New Orleans Saints in the early 2000s, and he continued that trend after he signed with Dallas before the start of the 2002 campaign.

8 Worst: Mike Vanderjagt


Perhaps the Cowboys should have paid more attention to Peyton Manning when he referred to Mike Vanderjagt as “our idiot kicker” while both were members of the Indianapolis Colts. Vanderjagt didn’t always have a reputation for being the best of teammates, but he was known to be a talented kicker when he signed with the Cowboys before the 2006 season.

7 Best: DeMarcus Ware

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It should be a matter of when, not if, DeMarcus Ware has his day in Canton at the Pro Football Hall of Fame. Truth be told, Ware may be a first-ballot Hall-of-Famer sooner rather than later. The Cowboys acquired Ware with the 11th overall pick of the 2005 NFL Draft, and Ware quickly showed he was worthy of such a high value.

6 Worst: Bryant Westbrook


It’s likely you’ll never read a post about bad free-agency signings made by the Cowboys without seeing Bryant Westbrook mentioned high on the list. Dallas offered Westbrook a deal before the 2002 season even though there were signs he wasn’t the player of old during his final season with the Detroit Lions, but the Cowboys only invested $1 million over a single year on his services.

5 Best: Jason Witten

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The modern NFL is a league where teams can acquire first-rate tight ends outside of first rounds of drafts. Jason Witten serves as one of the better examples. The Cowboys selected Witten in the third round of the 2003 NFL Draft, and he quickly showed he had first-round talent and the goods to become the best friend of a quarterback.

4 Worst: Bobby Carpenter


Bobby Carpenter may be the biggest draft bust of the century as it pertains to the Cowboys. Dallas selected the linebacker with the 18th overall pick of the 2006 NFL Draft, but the product of Ohio State failed to establish himself as a mainstay on defense during his time with the club.

3 Best: Terrell Owens


This is the first of two times Terrell Owens will be spotlighted in this piece. Nobody, not even the biggest T.O. critics out there, should pretend Owens didn’t provide a spark to the Cowboys during his first season with the club in 2006. Owens caught 85 passes and led the NFL in touchdown receptions with 13 during his debut Dallas campaign, and he followed that up by finding the end zone 15 times in 2007.

2 Worst: Terrell Owens

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How is it possible Terrell Owens can be among the best and worst Dallas players of the century? As great as Owens was during his first two seasons with the Cowboys, he was often a headache thought to care more about himself and producing stats than about wanting to win a title with the club. Owens complained when he felt he didn’t receive enough targets during games, and he quickly played his way out of favor as a member of the Cowboys.

1 Best: Tony Romo

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Critics and those who love to root against the Cowboys have mocked quarterback Tony Romo over the years for his inability to win a title and for his playoff miscues. Still, nobody can ignore Romo is, statistically speaking, the greatest regular season QB in Dallas history. Romo is the franchise’s all-time passing leader who holds numerous game, season and career records for the club, and the four-time Pro Bowl QB also showed he was a warrior willing to play through discomfort and injuries throughout the second half of his career.

Franchise QBs don’t grow on trees, and the Cowboys were fortunate to have such a talented player leading the offense for so long. Dallas fans can only hope Dak Prescott can follow in Romo’s steps now that Romo has officially walked off into the sunset.

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The 8 Best & 7 Worst Dallas Cowboys Of The 21st Century