Jordan made his WWE television debut on the May 31, 2003 episode of Velocity, where he defeated Jamie Noble. On June 26, 2003, Jordan made his first SmackDown! appearance as a face at Madison Square Garden, where he lost to 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. On the October 2 episode of SmackDown!, Jordan defeated Big Show via countout when Big Show had to run to the restroom after eating a burrito laced with laxatives. Jordan answered an open challenge hosted by Brock Lesnar on the January 29, 2004 episode of SmackDown!, where he was quickly defeated.
After an absence of multiple months, Jordan returned on the August 5, 2004 episode of SmackDown!, defeating René Duprée. Later in the night, Jordan turned heel by saving WWE Champion John "Bradshaw" Layfield (JBL) from an attack by the Undertaker. On the August 12 episode of SmackDown!, Jordan joined Layfield's Cabinet, where he was appointed "Chief of Staff". Jordan faced the Undertaker in the main event later that night, losing by disqualification after Layfield attacked Undertaker mid-match. On the August 26 episode of SmackDown!, Jordan once again faced Undertaker, this time with Layfield's WWE Championship on the line. The match once again ended in a disqualification after Layfield again interfered. On the November 25 episode of SmackDown!, Jordan and Layfield defeated Eddie Guerrero and Booker T, after interference from The Basham Brothers, who were made the Cabinet's "co-secretaries of defense" on the December 2 episode of SmackDown!. Jordan, Layfield and the Bashams were defeated by Booker T, the Undertaker and Eddie Guerrero in a 4-on-3 handicap match on the December 9 episode of SmackDown!. Jordan entered his first Royal Rumble match at the titular event on January 30, 2005, but was eliminated by Booker T.
After Layfield began a feud with John Cena over the WWE Title leading up to WrestleMania 21, Jordan faced off with Cena on the March 3 edition of SmackDown!. Orlando defeated John Cena with the help of Layfield to win the United States Championship, his first and only title in WWE. At WrestleMania 21, Jordan competed in a 30-man battle royal, won by Booker T. His first major successful title defense was against Heidenreich at Judgment Day. 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. 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 three 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. On the October 14 edition of SmackDown!, Jordan stated that he mastered every counter to Benoit's signature Crippler Crossface. Jordan also stated, if he tapped out to the Crippler Crossface, Jordan would quit this business. Jordan lived up to his words by countering every Crippler Crossface attempt by Benoit. The match ultimately ended after Jordan tapped out to Benoit's Sharpshooter. After those unsuccessful rematches, Jordan later broke away from Layfield, 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 to 1 in Booker's favor, Booker T only needed his replacement to win one match in order to become the United States Champion. Jordan approached him about the position, but Booker T and his wife Sharmell belittled him and made jokes about his quick submission losses to Benoit. Booker asked Randy Orton to substitute for him instead. After Orton failed to win the deciding match, leading Jordan to once again ask for the position the next week, Booker T once again turned Jordan down after belittling him. During the sixth match in the series, Jordan jumped the rail, grabbed Booker T's crutch, and hit Benoit for a disqualification finish and thus giving Benoit the victory and tying the best of seven series at 3 to 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 Benoit to win the series for Booker T. On the January 20 episode of SmackDown!, Jordan faced and lost to Randy Orton after Booker's wife Sharmell distracted the SmackDown! senior official referee Nick Patrick, before Booker hit him with a leg crutch. After the match, Chris Benoit saved him from Booker and Orton, turning him face for the first time since 2004.
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. On May 26, 2006, WWE announced that Jordan was released from his WWE contract.