Seven touchdown catches and over five hundred receiving yards earned Chester the Rookie of the Year award by the Newspaper Enterprise Association (NEA) and secured the first of four career Pro Bowl selections.

[2] His passion for sports began during his years at Frederick Douglass High School in Baltimore, where he excelled in track, wrestling, and football.

[3][4] In 1968, during the Bears’ 31-game unbeaten streak (1964-1968), including three seasons where they were undefeated (1965-1967),[5][6] Chester played in the match-up between Morgan State and Grambling.

[1] Chester was selected with the 24th pick in the first round of the 1970 NFL draft by the Oakland Raiders legendary owner Al Davis.

[10] Along with his 42 receptions, 556 yards, and 7 touchdowns, his performance earned him his first of four Pro Bowl selections (1970-1972, 1979),[11][12] and the NEA NFL Rookie of the Year Award.

[14] Chester was acquired by his hometown Baltimore Colts from the Raiders for All-Pro defensive end Bubba Smith on July 16, 1973.

[15][16] During his five seasons with the Colts he racked up 2,123 yards receiving, 11 touchdowns,[12] and was a key contributor to the team winning division titles in ’75, ’76, and ’77.

[19] Chester returned to the Raiders after being traded along with a 1979 second-round pick (33rd overall–traded to Tampa Bay Buccaneers for Dave Pear) from the Colts for Mike Siani and a 1979 third-round selection (72nd overall–traded to Houston Oilers), on July 21, 1978.

[14] In 2014, a campaign was launched by the Black Sports Legends Foundation to get Chester elected to the Pro Football Hall of Fame as well.