Jordan made his WWE TV debut on the May 31, 2003 episode of Velocity defeating Jamie Noble. On June 26, 2003, Jordan made his first SmackDown! appearance as a fan favorite at Madison Square Garden against then-villain John Cena. Although he did not win the match, he was impressive enough that when Cena attacked Jordan after the match was over, The Undertaker, with whom Cena was feuding, came to the ring and helped Jordan to his feet.
After being a fan favorite for several months, Jordan turned into a villain by joining John "Bradshaw" Layfield (JBL)'s Cabinet and being appointed as his "Chief of Staff". This happened when he saved J.B.L. from an attack from The Undertaker. A few months after joining, Jordan began changing his look by growing out his hair. While a part of The Cabinet, Jordan, along with the Basham Brothers (who became the newly appointed "Co-Secretaries of Defense"), helped JBL manage to keep his WWE Championship for nine months by interfering in his title matches against Eddie Guerrero, Booker T, the face run of The Big Show, and The Undertaker, who was the first person to show Jordan respect.
After JBL began a feud with a now-fan favorite John Cena over the WWE Title leading up to WrestleMania 21, Jordan faced off with Cena on the March 3, 2005 edition of SmackDown! from the Times Union Center in Albany, New York. Orlando defeated John Cena with the help of JBL to win the United States Championship, his first and only title in WWE. After losing his WWE Title to John Cena at WrestleMania 21, JBL stated that his Cabinet had been holding him back, which led to the departure of the Bashams. At The Great American Bash, Jordan began feuding with the newly drafted Chris Benoit. Jordan defeated Benoit and retained his United States Championship after removing the turnbuckle pad and shoving Benoit head-first into the exposed steel and covered him for the win. Feeling cheated, Benoit continued to chase Jordan for the title. He finally defeated Jordan (in a record 25.5 seconds) at SummerSlam to win the title. Following this quick match, Jordan attempted to win his title back on multiple occasions, leading to 3 consecutive losses with all matches lasting less than a minute. The first rematch lasted 23.4 seconds. During the second rematch, Jordan actually almost knocked out Benoit with a punch in the opening moments but still lost at 22.5 seconds, which was even faster than the first match. During the third match, Jordan stalled until the time, which was being displayed on the TitanTron, went over 25 seconds. He got so excited when his time went over 30 seconds that he dropped his guard and Benoit took the opportunity to lock on the Sharpshooter for a win at the 49.8 second mark. Earlier in the show, Orlando stated that he had mastered every counter to Benoit's signature Crippler Crossface, which was shown when during the match every time Benoit attempted the Crippler Crossface, Jordan countered it. After those unsuccessful rematches, Jordan later broke away from JBL, although both later made a few appearances together later on.
When Booker T got injured halfway through his Best of Seven series for the United States Championship, he needed a replacement to face Chris Benoit. As the series was at 3–1 in Booker's favor, Booker T only needed his replacement to win one match in order to become the United States Champion. Orlando approached him about the position but Booker T and his wife Sharmell laughed in Orlando's face and made jokes about Orlando's quick tap-out losses to Benoit. Booker instead asked Randy Orton to substitute for him. Orton, however, failed to win the deciding match, leading Jordan to once again ask for the position the next week. Booker T and his wife laughed at him and turned him down once again, however. During the sixth match in the series, Jordan jumped the rail, grabbed Booker T's crutch, and hit Chris Benoit for a disqualification finish. Chris Benoit was announced as the winner, tying the Best of Seven Series at 3–3. The next week, Jordan ran to ringside to attempt to halt Booker T from winning the Championship but was unable to prevent Orton from eventually beating Chris Benoit and winning the series for Booker T.
Jordan was then pushed down to Velocity and won several matches there. Jordan made his final SmackDown! appearance on the May 12 episode of SmackDown! in a backstage segment, telling Nunzio that he had seen someone who looked like his partner Vito dressed in drag at a night club during the recent UK tour. His final WWE appearance was a loss to Gunner Scott on the May 13 episode of Velocity.