Joining the World Wrestling Federation in 1996, JBL started his career as Justin Hawk Bradshaw on the night after WrestleMania XII with an impressive match against The Undertaker. Although it often felt he was on the cusp of a major push, he was underused for several years, despite many repackaging attempts, such as Blackjack Bradshaw and as a member of the Acolytes with Faarooq. Eventually, the Acolytes separated from the Ministry of Darkness, and they became the Acolyte Protection Agency, better known as the APA. They offered protection to anyone willing to pay them, in beer, cash, or preferrably both, and they remained a popular tag team for a few years during the WWF Attitude era.
Bradshaw gained a bit of a singles push during the WCW Invasion for his take-charge attitude backstage in the WWF, winning the European Championship (he also was very vocal backstage that incoming WCW stars should not usurp spots from the WWF guys through whom Vince McMahon won the Monday Night Wars, which was what happened in his football career when the NFL started placing guys into the World League of American Football, where JBL thought he had a stable position).
During the peak of the WWF Attitude, the wrestling business experienced a boom and wrestlers were getting interviewed by unlikely media outlets, including financial outlets. One such source interviewed Mick Foley for stock tips, but Foley said he was an extremely conservative investor and if they wanted to discuss stocks, they should talk to Bradshaw because he had success in the stock market. One thing led to another, and Bradshaw became a regular financial analyst on TV. He even wrote Have More Money Now, a finance piece for WWE Books.
During the initial brand split, the APA were drafted to separate brands and WWE hoped Bradshaw would be one of the first breakaway stars. Unfortunately, the fans did not support him as much as WWE had hoped so his push was stalled. The APA reformed for a couple more years (sound familiar?) until the APA had their last significant match at WrestleMania XX before Bradshaw was repackaged again.
Already an excellent WWE ambassador in financial press and the USO, WWE turned his gimmick into a self-made millionaire (not unlike The Million Dollar Man) and pushed him into main event status. As John Bradshaw Layfield (or "JBL" for short), he beat Eddie Guerrero for the WWE Championship at WWE's first Great American Bash and retained the championship for the next 280 days, before losing to John Cena at WrestleMania 21.
In addition to increased exposure on financial outlets, JBL continued to work with WWE for the next few years, including a stint on commentary for Friday Night Smackdown, until he decided on another run in the ring from November 2008 until April 2010, when he retired. His last official match was at The 25th Anniversary of WrestleMania, where he lost the WWF Intercontinental Championship to Rey Mysterio and promptly announced his retirement.