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Cowboys draft history: Best 21st century draft picks from each round

Round by round the best picks of the 21st century the Cowboys have selected.
Ali Jawad
Ali Jawad

The Landry Hat

Washington Redskins v Dallas Cowboys / Tom Pennington/GettyImages

Throughout the 64-year history of the Dallas Cowboys, the organization has been known for drafting and striking on some of the NFL’s all-time greatest players.

The Cowboys' most successful decades were in the 1970s and 1990s. Two different eras in franchise history that featured a combined five Super Bowl titles. Their success was fueled mainly by drafting the right players to help the franchise succeed. 

While the Cowboys have struggled to return to those glory days, unsurprisingly, the team has continued to draft and roster some of the best players we have seen in the 21st century. 

From impactful players to future and current Hall of famers and Diamond in the rough findings, let’s look at the Cowboys' best players drafted in each round in this century. 

Best First-Round Selection: Demarcus Ware, OLB

It has to be a no-brainer. When determining the Cowboys' best defensive player of this century, the first name that comes to mind is Hall-of-Fame linebacker Demarcus Ware. 

Ware will be enshrined in Canton, OH, on Aug. 5. He was the Cowboys' first-round draft selection in the 2005 NFL Draft. Number 94 would deliver nine memorable seasons wearing the star on his helmet. 

During his Cowboys career from 2005-2013. Ware totaled franchise-highs in sacks 117, forced fumbles 32, tackles for loss 145, and quarterback hits 185. 

In his Cowboys career, the former first-round pick would make seven Pro Bowls and seven All-Pro teams and is a member of the NFL 2000s All-Decade team. 

While Ware would finish his career in Denver, which included a Super Bowl ring earned in 2015. Cowboys fans will always remember him as one of the best players in franchise history and NFL fans will always remember him as a Cowboy first.

Runner Up: Dez Bryant

Best Second-Round Selection: Andre Gurode, C

Let’s see how many Cowboys fans remember that before Travis Fredrick, the Cowboys had one of the best centers of the 2000s in former second-round pick center Andre Gurode. 

He was drafted 37th overall in 2002 out of Colorado. Gurodes' first few seasons saw him playing guard and was in and out of the starting offensive line unit. In 2006 he won the starting job at center and developed into one of the best centers in the league. 

Between 2006-2010, Gurode was selected to five straight Pro Bowls and was named an All-Pro in 2009. In 2007, Gurode led a Cowboys offensive line that surrendered just 25 sacks that season. 

He was eventually released before the 2011 regular season due to issues with his left knee. Still, Gurode was as tough as a center could be. Just ask Albert Haynesworth.  

Runner Up: Sean Lee

Best Third-Round Selection: Jason Witten, TE

How about another no-brainer selection and a future-Hall-of-Famer? That's Jason Witten, who the Cowboys drafted in the third round of the 2003 NFL Draft out of Tennessee. 

In his 16-year career as a Cowboy, Witten exemplified greatness both on and off the field. 

On the field, Witten set numerous Cowboys records, including most career receptions (1,215), career receiving yards (12,977), and most games played (255). He was the Cowboys' iron man starting at one point 179 games straight, which also is a franchise record. 

Number 82 would appear in 11 Pro Bowls and was named an All-Pro four times in his Hall-of-Fame career. Overall Witten finished his career with 1,228 receptions, 13,046 receiving yards, and 74 touchdowns. 

Off the field, Witten has done his best to give back to the community through the Jason Witten SCORE Foundation. A foundation in which Witten and his wife, Michelle Witten, have helped several outreach programs and funded different projects. 

In recognition of his off-field work, Witten is one of four Dallas Cowboys to be recognized as the NFL Walter Payton Man of the Year. 

The next stop is Canton, OH and the Cowboys' Ring of Honor. 

Runner Up: Demarco Murray

Best Fourth-Round Selection: Dak Prescott, QB

Going into the 2016 season, the Cowboys were confident that quarterback Tony Romo could stay healthy and lead the team back into the postseason. The organization’s plans changed when Romo went down in preseason, and a battle for the starting job occurred. 

Little would the Cowboys know they would end up turning to their next franchise quarterback -- Dak Prescott, who was a near afterthought. 

Prescott was drafted out of Mississippi State in the fourth round of the 2016 NFL Draft. The former Bulldog probably never imagined he would lead Dallas to a 13-3 record and an NFC East title in his rookie season.

Well, that’s exactly what happened, and mid-way through his rookie season, it was clear that Prescott earned the right to be the starter moving forward. 

Prescott has led the Cowboys to the playoffs four times as a former fourth-round selection, has won three division titles, and has earned a pair of Pro Bowl selections. 

Statistically, Prescott has thrown 166 touchdown passes to just 65 interceptions. He has passed for 24,943 yards and has a career passer rating of 97.8. 

Let’s also credit what number four has done off the field. Prescott became the fourth player in franchise history to win the prestigious NFL Walter Payton Man of the Year award. 

Prescott’s Faith Fight Finish Foundation helps empower individuals, families, and communities to find strength through adversity. The foundation focuses on mental health, suicide, cancer, and youth. 

While some fans today may be growing restless and hope number four can deliver. It’s easy to put him on this list when considering the number of late-round quarterbacks who would go on to become franchise players is microscopic. 

Runner Up: Marion Barber 

Best Fifth-Round Selection: Orlando Scandrick, CB

As a former fifth-round selection out of Boise State in the 2008 NFL Draft, Orlando Scandrick carved out a lengthy 10-year career with America’s Team. 

Scandrick worked his way up the cornerback depth chart throughout his Cowboys career. He possessed the ability to play in the slot and on the outside. 

During his time in Dallas (2008-2017). Scandrick notched eight interceptions, seven forced fumbles, 11.5 sacks, and 362 tackles while playing in 125 games for Dallas.  

Despite never playing at a Pro Bowl or All-Pro caliber level, his leadership allowed Scandrick to play in Dallas for as long as he did. For years former linebacker Sean Lee was the leader of the Dallas defense. However, Scandrick was the voice of the coaches. 

Runner Up: DaRon Bland

Best Sixth-Round Selection: Dwayne Harris, WR/KR

We can always appreciate the importance of good, special teams. Just ask the 2010 San Diego Chargers. The addition of Dwayne Harris gave the Cowboys the spark they needed in the return game.

Coming out of East Carolina. The Cowboys selected Harris in the sixth round of the 2011 NFL Draft. Harris initially saw action as a wide receiver but was released mid-way through his rookie season. The Cowboys would eventually resign him towards the end of his rookie season. 

In 2012 Harris began to make his impact on special teams. The highlight of his 2012 season was in a week ten win against the Eagles in which Harris had his first career punt return for a touchdown, followed by a 78-yard return in the fourth quarter to help the Cowboys win. Harris finished second in 2012 in punt return yard average (16.1 yards). 

In four seasons (2011-2014) with Dallas, Harris had two punt return touchdowns, three seasons with 250 plus punt return yards and was named special teams player of the week four times. 

Considered to be one of the best special team players in franchise history, Harris left the Cowboys as their all-time leader in kickoff return yard average (26.5 yards) and the single-season average kick return yards in 2013 (30.6 yards). 

Runner Up: Anthony Brown 

Best Seventh-Round Selection: Jay Ratliff, NT

The best seventh-round selection turned out to be an easy find. Jay Ratliff, drafted in the seventh round out of Auburn in the 2005 NFL Draft, became one of the more surprising players to emerge.  

As an afterthought in the draft, Ratliff enjoyed a nine-year career (2005-2013) in Dallas. In his nine-season, Ratliff tallied 160 tackles, 46 tackles for loss, 57 quarterback hits, 27 sacks, four forced fumbles, and 13 fumble recoveries. 

The former Auburn Tiger would make four Pro Bowls (2008-2011) and was named a first-team all-pro in 2009. 

Not bad for a guy who was passed up 223 times.

Runner Up: Patrick Crayton

Best UDFA: Tony Romo, QB

Imagine finding a franchise quarterback after the draft. The Cowboys are one of the very few teams who accomplished that difficulty. 

As an undrafted longshot to make the team, Eastern Illinois Tony Romo hoped to become the long-term option at quarterback that the Cowboys had been searching for since hall-of-famer Troy Aikman retired after the 2000 season. 

For three consecutive seasons (2003-2005), Romo rode the bench and mainly saw action as a holder on special teams. His most important game came in the 2006 pre-season against Seattle when Romo showed exactly why he deserved the starting job. 

It wasn’t until midway through 2006 on a Monday Night game against the New York Giants. Romo came in and relieved struggling starter Drew Bledsoe. While it wasn’t the night Romo hoped for as he threw three interceptions. Dallas committed to number nine for the rest of the season.

After three in a half years on the bench, Tony Romo earned the starting job in week eight of 2006. He led Dallas to wins in five of his first six starts and helped the Cowboys make the playoffs with a 9-7 finish. He was selected to the 2006 Pro Bowl. 

Following the 2006 season, the search was over as Dallas had found their answer at quarterback. Romo would go on to lead the Cowboys for the next nine seasons.  

In his nine-and-a-half years as the starting quarterback, Romo led Dallas to the playoffs four times, won three NFC East titles, made four Pro Bowls, and was named a second-team All-Pro in 2014. 

The former UDFA would finish his career as the Cowboys' all-time leading passer. Romo passed for 248 touchdowns, 34,138 passing yards, and an astounding career passer rating of 97.1

His gunslinging and daring escapes fueled some of the most memorable moments in franchise history.

From an undrafted long shot to a Pro Bowl starting quarterback for America’s team, Tony Romo made the most of his opportunity and is unquestionably one of the greatest UDFA ever. 

Runner Up: Miles Austin

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Ali Jawad

Ali Jawad

Ali Jawad joined FanSided as a contributing writer and writes for Dunking with Wolves. Jawad recently worked for the New York Giants as a Digital Platform Intern, helping oversee Giants.com and the Giants app. He has previously worked for networks and organizations such as NBC Universal, Pro Football Network, and Dallas Cowboys.