In both 1996 and 1997, Jackson was a starter for the Cougars and was considered a favorite target of Ryan Leaf. After going undrafted in the 1998 NFL Draft signed with the Tampa Bay Buccaneers and spent the season on their practice squad. Following his stint in Tampa Bay he would spend three seasons split with the Seattle Seahawks and Tennessee Titans. In 2000, after his fIrst stint in the NFL was over, Jackson signed with the AFL's Los Angeles Avengers. He spent three seasons with Los Angeles and was named the AFL's Rookie of the Year and totaled 3,255 yards, 238 catches and 67 touchdowns. After the Avengers, Jackson was given another opportunity in the NFL to play for the Green Bay Packers in 2002 and 2003.