He is now on a route that appears inevitable - despite a three-year prison stint and only three fights since his release.
His prison stint was due to working for Jack Dalton.
During his second prison stint, from 1967 to 1977, he first saw the potential for a new career in helping American corporations crack the Chinese market.
In one interview between prison stints, Askari X referred to jail as "the hidden university," saying that he wrote much of his rap material there.
Kirkland was once one of the most prominent rising junior middleweights in the world before an 18-month prison stint knocked his career off track.
After a prison stint in the mid-seventies, Leary toured the lecture and club circuit as a "stand-up philosopher."
Martha Stewart fans hoping for details of her recent prison stint will have to keep waiting.
They added that they believed that her potential for drawing a large television audience could be much larger after her prison stint.
Unfortunately, during his prison stint, his daughter Lorraine had died in a car accident.
She scowled as if they were still a couple, and their time together hadn't been interrupted by his prison stint.