After being trained in FCW, Stephens debuted on the July 18, 2008 episode of SmackDown, as The Brian Kendrick's bodyguard under the name Ezekiel. On the August 8, 2008 edition of SmackDown, his ring name was tweaked to Ezekiel Jackson, and he was revealed as being Kendrick's "advisor". He then began interfering in Kendrick's matches against Jeff Hardy, Finlay, and WWE Champion Triple H. On the October 17 edition of SmackDown, Jackson made his official in-ring debut by squashing Super Crazy, after replacing a supposedly sick Kendrick. In late 2008, Jackson began teaming with Kendrick and both began feuding with the WWE Tag Team Champions The Colóns (Carlito and Primo), although Kendrick and Jackson failed to win the championship. He suffered his first defeat on the February 13, 2009 episode of SmackDown, when he lost a singles match to R-Truth. Jackson made his final appearance on the SmackDown brand in a losing effort against Jeff Hardy on the April 3, 2009 episode.
On April 15, 2009, Jackson was drafted to the ECW brand as part of the 2009 Supplemental Draft, therefore breaking up the team of himself and Kendrick. Jackson returned to FCW for further training, however, without making an immediate appearance for the brand. He made his ECW debut defeating Jack Meridol, a jobber—a wrestler who consistently loses to make his opponents look stronger—on the July 9, 2009 episode. Jackson then began an angle with Vladimir Kozlov in which, week after week, after one of them had squashed a local competitor, the other would come out and hit their finishing move on the fallen opponent in a game of one-upmanship. On the August 18 episode of ECW, Jackson formed an alliance with Kozlov and William Regal, betraying the ECW Champion, Christian, during a tag team match to side with them, and attacking Christian at Regal's request. Kozlov and Jackson aided Regal in his feud with Christian over the ECW Championship, but Regal was unable to capture the title. This alliance ended on November 24th edition of ECW when Jackson attacked Kozlov and Regal. Jackson turned face as a result. After a few weeks, William Regal turned on Kozlov, siding with Jackson, both kicking Kozlov out of the Roundtable.