Jindrak made his WCW debut on the March 2, 1999 taping of WCW Saturday Night, teaming with Chuck Palumbo as "The Soul Surfers" in a loss to Disorderly Conduct. He was promoted to the main WCW roster in June 2000, where he formed a tag team with Sean O'Haire. In August 2000, Jindrak and O'Haire helped form The Natural Born Thrillers with Mike Sanders, Shawn Stasiak, Chuck Palumbo, Johnny "The Bull" Stamboli, and Reno. They were briefly "coached" by Kevin Nash. In September 2000, Jindrak won the World Tag Team Championship with O'Haire for the first time, despite being relatively new in the business. The pair won the World Tag Team Championship once more before splitting in early January 2001 when Jindrak would begin teaming with Stasiak instead. The team was short-lived, as Stasiak went on to pick up the managerial service of Stacy Keibler and Jindrak was taken off of television.
After the World Wrestling Federation purchased WCW in March 2001, Jindrak came into the company in July 2001 as part of The Alliance that invaded the WWF roster. Jindrak wrestled in dark matches and at house shows throughout July. His first televised debut was on the July 28, 2001 episode of Jakked, defeating Jerry Lynn. He returned to the WWF (now renamed WWE) on the October 13, 2002 episode of Sunday Night Heat, defeating Justin Credible. He made a few more appearances on Heat in late 2002, defeating wrestlers such as Credible, Raven and Stevie Richards until suffering an ankle injury.
After being considered as part of the Evolution group, Jindrak made his Raw debut on July 7, 2003 as a face, where he was defeated by Chris Jericho. He then began to tag team with Garrison Cade on the Raw brand. The two feuded with teams such as La Résistance, Evolution and The Dudley Boyz. The team soon separated when Jindrak was drafted to the SmackDown! brand on March 22, 2004. He made his debut as a member of SmackDown on its secondary show Velocity, during which he appeared as "The Reflection of Perfection", a narcissistic heel gimmick obsessed with his own physique. On April 8, 2004, Jindrak gained Theodore Long's managerial services for a brief period until the pair split in July when Long turned face and became the general manager of SmackDown!, while Jindrak remained on Velocity. In September, Jindrak aligned himself with Kurt Angle and Luther Reigns to assist Angle in assaulting and shaving Big Show bald during the fifth anniversary episode of SmackDown!. Jindrak and Reigns continued to serve as Kurt Angle's proteges until February 2005, at which point they split from Angle to continue their own feud with The Undertaker. However, Jindrak and Reigns' team began to have a falling out, most notably after they lost to Undertaker in a "Double Jeopardy" handicap match on the February 24, 2005 episode of SmackDown! because of Jindrak submitting to a triangle choke. The following week, Jindrak and Reigns lost a WWE Tag Team Championship match against Eddie Guerrero and Rey Mysterio. Following the loss, Jindrak turned face by getting into a fight with Reigns and knocking him out with a left hook. On the March 10 episode of SmackDown!, Jindrak defeated Reigns in a singles match. After this, Jindrak became a low-card star who performed on Velocity and only appeared on SmackDown! to job against other wrestlers, during which he alternated between face and heel alignments. On the May 28 episode of Velocity, Jindrak unsuccessfully faced Orlando Jordan for the United States Championship. He then wrestled his last match on the SmackDown! brand on the June 18 episode of Velocity, which he lost to René Duprée. On June 30, Jindrak became one of the last minute trades in the 2005 WWE Draft, returning him back to the Raw brand. However, Jindrak never made his Raw re-debut, as he was released from his contract on July 5, 2005.