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Jay-Z’s partnership with Creative Artists Agency (CAA) for the Roc Nations Sports agency venture is facing a dilemma–a dilemma that could put his aspirations in jeopardy.

The National Football League Players Association (NFLPA) said that Jay-Z cannot sign players unless he becomes certified by the association.

In a FORBES report, rival agents made a fuss about Jay-Z entering their world unencumbered, saying that Jay-Z violated a rule set by the NFLPA that he isn’t allowed to sign players to CAA until he’s gained his certification.

CAA recently recruited New York Giants star player Victor Cruz away from another agency, causing the mild controversy. Although Jay’s recruitment of Cruz is a violation, the NFLPA excused it on the merit of the pair’s longstanding friendship. To be clear, CAA agent Ben Dogra is listed as Cruz’s contract advisor and keeps Jay off the hook.

Jay-Z himself now aspires to join the fray in order to help close deals himself as an agent. Liz Mullen of SportsBusiness Journal tweeted yesterday (April 15), “Jay-Z’s sports agency will hire established agents in multiple sports as well as have its own employees, including Jay-Z himself, certified.” It was also noted that the soonest Jay-Z can take the NFLPA’s test in January 2014. Further, Jay does not have a post-graduate degree; he will have to prove he has at least seven years of negotiating experience in order to be certified. As the former President of Def Jam and current head of Roc Nation, Jay-Z has done his share of deals.

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