Jennings was born in Birmingham, Alabama, the second of three sons born to Edmond and Paulette Jennings. He is a cousin of NFL lineman Andre Smith. At Pinson Valley High School in Pinson, Alabama, Jennings lettered in baseball, football and basketball. He received an offer from the Georgia Bulldogs to play both baseball and football collegiately.\n', '

Jennings was selected by the Cleveland Indians in the 18th round of the 2005 amateur draft out of Pinson Valley High School but did not sign. After failing to qualify academically for the University of Alabama, Jennings decided to enroll at Itawamba Community College to play baseball and football; he led all junior college wide receivers with 54 receptions while scoring 6 touchdowns and netting 848 yards in 8 games. On the diamond, he hit .378 with 29 steals. Jennings was picked by the Tampa Bay Devil Rays in the 10th round of the 2006 amateur draft and signed.\n', '

Jennings was the Rays\' fifth-best prospect heading into the 2009 season according to Baseball America, and the 18th-best prospect overall in their midseason top 25.\n', '

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