After training under his childhood friend, mentor, and perpetual superior John Phoenix (alias John Couch), Massengale made his professional wrestling debut with a local promotion in 1998 at Walter B. Williams Gymnasium in Milledgeville, GA. Jason Cross later appeared in NWA Wildside in mid-2001 where he, Adam Jacobs, John Phoenix and Prince Justice defeated A.J.
Cross held the title for exactly one month before losing it to Ray Gordy and remained within NWA Wildside until its closure in 2005.
On January 15, 2003, Cross suffered a broken hand and a crushed knuckle in a losing effort against David Young.
[2] Cross is retired from professional wrestling and lives a quiet life in rural Georgia.
He spends his time writing children's books and collecting taxidermy replicas of famous television cats.