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His main career start was in music promotion, where he managed such acts as M. C. Hammer, New Edition, Whitney Houston and Mary J. Blige, and he branched out to other entertainment areas, such as when he worked with Eddie Murphy.
Around 2000, Al ventured into boxing when he started managing Vernon Forrest. Over the next decade, Haymon gained considerable influence in boxing, mainly due to his connection to Floyd Mayweather Jr. In 2005, Haymon won the Al Buck Award (Manager of the Year) from the Boxing Writers Association of America.
Haymon has been the subject of much criticism and controversy in the boxing world.
While Haymon maximizes fighters' incomes, it is argued that he does so at the expense of a fighter's health and there have been accusations that he facilitates false records being submitted to boxing commissions.
Haymon's influence has been seen as gaining fights for his fighters prime spots on HBO, but these fights are seen as less than quality match-ups and instead easy fights to expose his fighters and this influence has been questioned by Max Kellerman of HBO Sports.