Mob ties like Sinatra

from Jay Z (Ft. The Notorious B.I.G.) – Brooklyn's Finest Lyrics on Rap Genius

Meaning

Frank Sinatra was often rumored to have extensive Mob ties, going so far as to allegedly run money to Cuba for them. The Mob-connected singer Johnny Fontaine in the Godfather book and films was, much to the singer’s displeasure, based on Sinatra

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