The union is planning to send a letter of inquiry to Roc Nation Sports agent Kim Miale to gather more information about Jay-Z's involvement in courting Smith. The recently instituted "runner rule" prohibits agents from having colleagues or friends who aren't NFLPA certified agents present for recruiting meetings.
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Earlier this week, Smith's adviser John Thornton, a former NFL defensive tackle, was quoted by CBS as saying "I was in those meetings, and Jay-Z connected with him on many levels." Thornton later said he was misquoted.
The real smoking gun might be a picture that Smith posted of Jay-Z and himself on Instagram during the quarterback's recent re-recruitment process, which kicked off after Smith fired agent Jeff Nalley.
The NFLPA previously sent a letter of inquiry to CAA mega-agent Tom Condon after Condon signed Victor Cruz, who is using Roc Nation for his marketing. Roc Nation has established a partnership with CAA in sports other than football, where the runner rule makes such an arrangement problematic. The union cleared Condon of wrongdoing.