Grimes was moved to the Memphis developmental territories before being brought up to television under the ring name Key.
As Key, Grimes portrayed a drug dealer character along with Droz and Prince Albert and feuded with The Godfather.
There, Grimes joined Tony DeVito and Spanish Angel, replacing P. N. News, in Da Baldies.
During Living Dangerously in March 2000, a breakdown in communication between New Jack and Grimes led to both men tumbling off a 20-foot high scaffolding rig onto concrete.
[3] Other major points of the feud featured New Jack diving off the Los Angeles Grand Olympic Auditorium balcony over 30 feet onto two tables, with Grimes on top of both, at Redemption in May 2001, as well as Grimes throwing New Jack off the same balcony through many tables stacked below at New Year's Revolution in January 2002.
Grimes broke his fall on the top rope, dislocating his ankle and suffering multiple other injuries in the process.
Some believe this to have been a 'work' on New Jack's part as closer inspection of the footage appears to show that Grimes threw himself off the scaffolding at an unexpected angle and with more velocity than intended.