(Editor's Note: Who doesn't love lists? Throughout training camp, 'High 5' will provide a top five list for many of the critical topics surrounding the Dallas Cowboys 2025 season.)
For two teams that have only met nine times since the turn of the century, there are plenty of familiarities between the Dallas Cowboys and Chicago Bears this week. The Bears are the Cowboys' least-common conference opponent and it's the second-fewest meetings out of any NFC pairing over that period.
Despite that, this week marks a homecoming or first meeting for many significant parts of both organizations. Matt Eberflus makes his return to Chicago where he coached from 2022-24, while Jack Sanborn returns with him. Al Harris and Nahshon Wright will also play their former team, now a part of the Bears organization.
With all the focus on reunions between the two franchises, let's explore the best players to have worn both a Cowboys and Bears uniform. Here are the top five players who made an impact with both organizations during their NFL playing years:
5.) Marion Barber III
If Marion Barber would've played for multiple seasons in Chicago, he'd probably be higher on this list. He was drafted in the fourth round of the 2005 NFL Draft and played six productive seasons in Dallas. Barber finished with 4,358 rushing yards and 53 total touchdowns with the Cowboys and earned Pro Bowl status in 2007. Ending his time in Dallas by playing through injury before being released in the 2011 offseason.
Barber then signed a two-year deal with the Bears and quickly won the backup job behind starter Matt Forte for the 2011 season. Despite some early-season injuries and a timing mishap in Week 14 against the Broncos, he pieced together a productive campaign with Chicago, finishing with six touchdowns and 422 rushing yards. Instead of playing the second year of his contract in Chicago, Barber decided to retire before the 2012 season.
4.) Jay Ratliff
Jay Ratliff is another former Pro Bowl caliber talent for the Cowboys that made a late-career jump to Bears. He was named to four-straight Pro Bowls from 2008 to 2011 and was named an AP First-team All-Pro in 2009. Ratliff played eight successful seasons in Dallas before a controversial injury prompted a release by the Cowboys in October of 2013.
After being medically cleared, Ratliff signed a one-year deal with the Bears to finish the 2013 season. He made four starts that season and tallied 14.5 tackles, 1.5 sacks, and one tackle four lost in limited playing time. This sparked a two-year contract for Ratliff to remain in Chicago, where he was one of the best players on the Bears defensive front in 2014. Finishing second on the team with 6.5 sacks and 33 pressures despite missing five games due to injury.
3.) Martellus Bennett
Known for his sense of humor and two-sport athleticism at Texas A&M, Martellus Bennett locked in on football and made an immediate impact upon arriving in Dallas. He caught four touchdown passes in 20 total receptions as a rookie in 2008. However, those were his only touchdowns as a Cowboys tight end, as he struggled to replicate that success behind Jason Witten for the rest of his Dallas tenure.
Bennett moved on from Dallas by signing with the Giants as a starting tight end in 2012 and had a resurgent season in New York, leading to a four-year contract with the Bears. He made a massive impact with Chicago, earning Pro Bowl honors in 2014 and tallying over 2,114 receiving yards and 14 touchdowns over three seasons with the Bears.
2.) Chuck Howley
Following a stunning career at West Virginia, Chuck Howley was drafted by the Chicago Bears and played two seasons in Chicago before suffering a severe knee injury in 1959 that appeared to be career-ending. He only played in 15 games as a Bears defender before the injury.
In 1961, Chicago traded his rights to the Cowboys upon news that he was attempting a comeback. Howley played 13 seasons in Dallas, winning Super Bowl VI along with being named Super Bowl V MVP. He also accumulated five All-Pro selections, six Pro Bowls, and a Pro Football Hall of Fame career. Howley became just the fourth player to be inducted into the Cowboys Ring of Honor.
1.) Mike Ditka
Most of the younger generation remembers Mike Ditka for his coaching career and television antics. Before his sideline success, he was an extremely productive tight end during his playing career that began in Chicago and ended in Dallas.
Ditka burst on the scene with 1,076 receiving yards and 12 touchdowns as a rookie in 1961 and finished his time in Chicago with 4,503 yards and 34 scores over six seasons. After spending two seasons in Philadelphia, he was traded to the Cowboys in 1969 and played four years in Dallas, finishing with a Super Bowl VI win before retiring in 1972.
Upon retirement, he was hired on to Tom Landry's staff and served as an assistant coach and special teams coordinator until Chicago hired him as head coach in 1982.
