#3 R-Truth
Age: 46
Years in the wrestling business: 21
The reason he might retire: Accumulated injuries, a new focus on his music career.
Ron Killings, better known to the world as WWE's R-Truth, began his career working for NWA in its post-JC Productions era. But despite being scouted by Jackie Crockett herself, he eschewed a wrestling career to focus on his hip-hop music. After two years of struggling to break into the music industry, he wound up calling Crockett and expressed interest in being a wrestler.
R-Truth was trained and brought into the business by none other than the legendary Manny Fernandez, a major star during pro wrestling's regional era. The Raging Bull taught R-Truth not only how to wrestle, but how to conduct himself in the business.
Truth wound up signing with WWE in 1999 under the name K-Kwik. He had two reigns as Hardcore Champion but otherwise failed to make an impact. He wound up returning to the indies and had a successful run in TNA, where he won the NWA title before the organization split from Jarrett's program.
R-Truth would eventually return to the WWE, where he has become a mainstay. His appearances have been more sporadic, because of many injuries accumulated during his long career. While R-Truth has not said anything specific about retirement, he has stated he would like more time to focus on his music career.