Jackie Kellogg started his decade of pro ball in the NFL with the San Francisco 49ers but his real success was in the CFL for 8 seasons with the Calgary Stampeders and the Edmonton Eskimos from 1995 till 2002. He helped the Calgary Stampeders win the Grey Cup in in 1998. Jackie also played in a total of 14 CFL playoff games, including four Grey Cups. Among his many awards, this star Defensive Back was selected to the Westem Allstar Selection Team.