McCaskill (6-4, 300/Hampton/Tallahassee, FL) was originally signed as a free agent by the Buffalo Bills on July 28, 2007 and was a member of the Bills practice squad for parts of the 2007 season. He also participated in the Bills 2008 training camp before being waived on Aug. 31, 2008. McCaskill spent time in 2008 on the Philadelphia Eagles practice squad before he was signed to the Green Bay Packers active roster on Dec. 11, 2008, where he was inactive for three games. He was waived by the Packers on June 29, 2009.