Jennings began his high school career at Jefferson Forest High School in his hometown, Forest, Virginia. As a fifth string running back, he didn't play in a game until the last game of his junior year. As a self-described "270 lb. chubby kid with asthma and glasses", Jennings finally played after the first four running backs ahead of him on the depth chart went down with injuries. Even before putting in Jennings, his coach attempted to play a wide receiver at running back. On his first handoff he ran the ball in for a 30-yard touchdown. After a 40-yard rushing touchdown and scoring 2 more touchdowns on defense, Jennings was approached by a scout from the University of Tennessee who had come to see the starting running back. After inquiring about his grades and discovering Jennings had a 0.6 GPA, the scout said "Son, you have potential... Get your grades right!"
After the encouragement, Rashad and his brothers decided it would be best for him to transfer to Lynchburg Christian Academy. His older brothers offered to coach the football team since he couldn't afford the tuition at the time. At LCA, he would begin to shed some weight and take to learning after having to repeat his junior year. In his junior and senior year, he was a two-time All-VISAA Division II selection while totaling 3,287 yards and 56 touchdowns, including 1,978 rushing yards and 28 touchdowns as a senior, while also lettering twice in basketball
Jennings began his college career at Pittsburgh in 2005, only the fourth true freshman running back to start there. However, Jennings transferred to Division I-AA Liberty, in spring 2006, to be closer to his family. Though Jennings was suspended for the first two games of the 2007 season due to an internal violation, he excelled at Liberty, setting a Big South Conference record with 3,633 yards, 42 touchdowns, and averaged 5.7 yards per carry.
After being coached by the Jacksonville Jaguars' staff during the 2009 Senior Bowl, Jennings was drafted by Jacksonville in the seventh round (250th overall) of the 2009 NFL Draft. He scored his first career touchdown in Week 9 against the Kansas City Chiefs, rushing for 28 yards. After a promising rookie season, Jennings's 2011 was cut short by injuries—after suffering a concussion in the Jaguars' first preseason game, and his knee injury two weeks later, Jennings was placed in injured reserve before the regular season began.
Due to a contract holdout by starter Maurice Jones-Drew, Jennings was named the starting running back for the team's 2012 regular season opener against the Minnesota Vikings. Jones-Drew returned to the starting lineup the following week Jennings resumed his role as a backup until a shoulder injury on December 24, 2012 landed him on injured reserve for the second consecutive year.
Jennings was signed by the Oakland Raiders on April 10, 2013.
Jennings started the 2013 season backing up starter Darren McFadden. McFadden spent much of the season plagued by injuries forcing Jennings to start eight games in his place. Jennings, a career backup, exceeded expectations as a starter and saw his best rushing game of the season in week 11 against the Houston Texans where he rushed 22 times for 150 yards (6.8 ypc) and one touchdown on the end of an 80-yard rush. Jennings finished the season with 733 rushing yards on 163 carries and six touchdowns.
On March 12, 2014, Jennings signed a four-year, $14 million contract including $3 million guaranteed with the New York Giants. Jennings quickly took over as starter, starting 9 games out of the 11 that he played. Jennings rushed for 639 yards on 167 carries and scored 4 rushing touchdowns.
Jennings played in 13 games, rushing for 593 yards, his lowest total since 2013, and scored 3 touchdowns on 181 carries. Jennings added 35 receptions for 201 receiving yards and 1 receiving touchdown in 2016.
Jennings was released by the Giants on February 13, 2017.
On March 1, 2017, Jennings was revealed as one of the contestants who would compete on Season 24 of Dancing with the Stars. He is paired with professional dancer Emma Slater.
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