In his MuscleTime DVD Darrem stated that his net worth was about a million dollars. It's fully believable in my opinion that he has earned enough money in his lifetime to be a paper millionaire, if not having that much in liquid cash. Darrem seems to want his son to be a bodybuilder and if Renel has the genetics I am sure he can do it for a living just as Darrem did. Any pro at Darrem's level can make enough money from bodybuilding alone if they market themselves right. The pros that go broke were just not particularly smart at managing their money or their careers for that matter.
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Indeed. From an FLEX article he did (the issue with him on the cover), he explains how he made a living before securing his first contract in 2000.
He'd been a pro since 1992. Basically, he used to own his own gym in Trinidad. But, his partner swindled him out of his money, when he moved to the U.S.
He basically worked as a personal trainer, had a beat-up car and stayed in modest apartment. He had to do that for a year, on his own, before he saved up enough money to move his wife and son to the U.S.
Charles saved, invested, and managed his money. Business picked up when Weider finally signed him in 2000. In 2002, he won his first show.
MuscleTech picked him up later and he's started rolling. He won the Maximus Pro show in Italy, upsetting Markus Ruhl in the process. I personally saw his win the Florida Pro Xtreme show in Orlando, back in 2004. Charles had the honor of winning the first New York Pro show i '05 (after DeMilla quit the IFBB and took the name "Night of Champions" with him).
So, overall, he has simply stuck with it, despite criticism that he didn't have what it took to be a top pro. Until this year, Darrem Charles had won at least one show since 2002. But, per another FLEX article, the Trinidad-and-Tobago-born superstar got stuck with a certain reputation. That article actually referred to him as a 'Pirate from the Carribean', claiming that he was best for winning "small" shows (when other Olympia competitors had already qualified and sat the later shows out).