The 8 Best & 7 Worst Dallas Cowboys 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.

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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.

Following the 2015 campaign, Pro Football Focus rated Frederick their best overall center for the second straight season. Those of you who don’t watch All-22 film on a weekly basis may not notice what Frederick contributes to the club on football Sundays, but nobody should discount what he has meant to the Cowboys since the franchise drafted him. He truly has Hall-of-Fame talent.

14 Worst: Dwayne Goodrich

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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.

His stint with the Cowboys ended in February 2003, roughly one month after he was involved in a hit-and-run accident that resulted in the deaths of two individuals. As Chris Low of ESPN explained, Goodrich was convicted of criminally negligent homicide with a deadly weapon and failure to stop and render aid, and he served six years for his involvement in that horrific crime.

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.

Smith has already been named to four straight Pro Bowl squads from 2013 through 2016, and he's a two-time first-team All-Pro who could be recognized as the NFC’s best left tackle of the decade. While Prescott and running back Ezekiel Elliott earn headlines and praise because they play more exciting positions, both men owe linemen such as Smith, Travis Frederick, Zack Martin and other members of the club’s front wall quite a bit of gratitude.

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.

In February 2016, Gregory was suspended after he allegedly violated the league's substance abuse policy, and that proved to be only the beginning of his problems. He failed yet another test in November of that year, and it was reported in January 2017 that he's currently facing a year-long suspension after he once again violated the league’s substance abuse policy. It’s anybody’s guess when, or maybe if, Gregory will again take the field for the Cowboys.

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.

Yes, Bryant will likely always be remembered by some for the controversial non-catch that occurred during a January 2015 playoff game versus the Green Bay Packers, and it’s true he has been somewhat overshadowed by the likes of Odell Beckham Jr. and other talented receivers. Bryant is still one of Dallas’ best draft picks of the current decade.

10 Worst: Ebenezer Ekuban

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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.

Ekuban failed to impress head coach Bill Parcells, so much so that Parcells deactivated him for a game versus division rivals the Philadelphia Eagles in December 2003. In total, Ekuban registered only 12.5 in 34 starts across five seasons before the Cowboys parted ways with the player. In fairness, Ekuban did go on to find success playing for the Cleveland Browns and later for the Denver Broncos.

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.

Glover solidified himself as one of the best defensive tackles in the NFL featuring up front for the Cowboys, and he played a massive role in helping what had been a lackluster club make a return to the playoffs. In total, Glover accumulated 21.5 sacks and five forced fumbles during his four seasons with the Cowboys before he moved on and signed with the St. Louis Rams. He was worth every penny Dallas paid him.

8 Worst: Mike Vanderjagt

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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.

A veteran at that point of his career, Vanderjagt was slowed by an injury during the preseason, and he then missed a pair of field goals during the club’s final exhibition contest of the summer. That was only the beginning of his woes, as he converted 13 of 18 field goal attempts and seemed to have a weak leg during his brief stint with the club. Dallas released him after 11 games.

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.

He made nine Pro Bowl teams and was a four-time first-team All-Pro during his Dallas career, and he accumulated a total of 117.0 sacks in nine seasons with the Cowboys. While he never managed to play in a Super Bowl as a member of the Cowboys, he finally won a ring as a member of the Denver Broncos squad that defeated the Carolina Panthers at Super Bowl 50.

6 Worst: Bryant Westbrook

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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.

It’s almost as if Jones and company could see into the future. Westbrook was repeatedly targeted and humbled by rookie quarterback David Carr during the first game ever played by expansion team the Houston Texans, and the cornerback committed multiple penalties in a losing effort. Dallas cut him after that one awful appearance for the club.

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.

Witten made his first Pro Bowl squad for his work during the 2004 campaign, and he has since been to ten Pro Bowl rosters and been a first-team All-Pro on two occasions. The 35-year-old who holds multiple franchise records has to be considered one of the best offensive players to ever feature for the Cowboys. He's a lock for the Hall of Fame and should be inducted not long after he officially retires.

4 Worst: Bobby Carpenter

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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.

These days, Carpenter is largely remembered for being a pick that never should’ve been made and also for being called “Barbie Carpenter” by teammates during a practice session that was filmed for the television show Hard Knocks. According to Pro-Football-Reference.com, Carpenter started in three games across four seasons for the Cowboys, during which he accumulated 3.5 sacks and 96 total tackles. The franchise traded him to the St. Louis Rams after the 2009 campaign.

3 Best: Terrell Owens

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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.

Owens was still, on the field, one of the best offensive weapons in the NFL during this portion of his career, and he has to be considered to be one of the most talented Dallas players of the decade even if he was a polarizing figure who also failed the Cowboys in multiple ways.

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.

By the end of the 2008 season, the Cowboys had enough and elected to release Owens. There’s no question Owens belongs in the Pro Football Hall of Fame and should be recognized as one of the greatest receivers in league history, but one has to wonder if the Cowboys would have been better off without him.

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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