Roland played college football for the Missouri Tigers, earning consensus All-American honors as a defensive back in 1965.

He was the star running back of the first racially integrated high school team to win a Texas state football championship.

After his playing days, he served as an assistant coach with the number of NFL teams and at the University of Notre Dame.

[2][3] On the way to the 1960 championship, the Buccaneers won three playoff games to reach the finals, including a win against Port Arthur which was led by future college and NFL hall of fame coach Jimmy Johnson.

Roland had 103 yards rushing in the title game, including a 37-yard touchdown run in the 13–6 victory.

It was later reported he had nothing to do with the theft, and his coach Dan Devine would not have blamed Roland for leaving Missouri for another school.

[2][5][6] In 1965, Roland led the Tigers to an 8–2–1 record and a victory in the 1966 Sugar Bowl over the Florida Gators and Steve Spurrier, 20–18, in which he threw a touchdown pass.

[5] Roland had his jersey retired (#23) by Missouri and was inducted to the College Football Hall of Fame in 1998.

[6][15][16] Roland was hired by Chicago Bears head coach Mike Ditka in 1983 to help coach running back Walter Payton,[17] who at the time stood 2,108 yards from Jim Brown's NFL rushing record; breaking the mark in 1984.

[5] During Roland's tenure, the Bears led the league in rushing four times, and finished among the top three in seven of his 11 seasons.

From 1984 to 1988, Chicago rushed for 160.9 yards per game, went 62–17 (.785), made the playoffs five straight years and won Super Bowl XX.

During his final season with the Cardinals in 2003,[5] he coached Emmitt Smith who was traded by the Dallas Cowboys in the offseason.

[5] Haslett was fired the following season and replaced with Sean Payton, who chose not to retain Roland.