Raynor graduated from South Johnston High School in 2002. He attended the University of North Carolina at Wilmington. in 2005, for UNCW, he hit.397 with 23 stolen bases. Raynor was drafted by the Baltimore Orioles in the 12th round of the 2005 Major League Baseball Draft, but did not sign.
In 2006, his senior season, he hit.370 with 42 stolen bases.
In the 2006 Major League Baseball Draft, Raynor was selected in the 9th round by the Florida Marlins and signed by scout Joel Matthews.