In August 1998, Jamize began playing Pop Warner football for the San Bruno Rams in Northern California where he and his older brother would begin their gridiron journey.

Jamize playing running back while big brother (Millicent Olawale) was the star quarterback.

He being a respectful young man, exceptional student as well as an athlete, all attest to his Father’s strict but meaningful upbringing.

[1][2] Olawale played two seasons at El Camino College as a tight end, recording 15 receptions for 338 yards and three touchdowns.

[9] On December 4, 2012, the Oakland Raiders hampered by injuries to running backs Darren McFadden and Mike Goodson, signed Olawale from the Dallas Cowboys practice squad.

[17] On November 21, 2016, against the Houston Texans, he had a 75-yard receiving touchdown from quarterback Derek Carr in the 27–20 victory at Azteca Stadium.

[20] In March 2018, the Raiders traded Olawale and a 2018 sixth-round pick (#192-Jamil Demby) to the Dallas Cowboys in exchange for a fifth-round choice (#173-Johnny Townsend).