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.
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.
Smith is Miale's third client, per NFLPA records, following linebacker Brandon Hicks, who spent time in the Bills' and Steelers' training camps the last two summers, and arena league kicker Carlos Martinez.
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.