Wendy Day made for an unlikely rap fan, and even less a champion of the oppressed hip-hop recording artist. She was white, overweight, and in her 30s. Incongruously, she wore Timberland boots, baggy Cross-Colors outfits, and attended classes on Afrocentricity. Few knew what to make of her. But Day put her own money where her mouth was, spending the half-million dollar fortune she made in marketing and advertising on a non-profit organization called the Rap Coalition, with the expressed goal of rescuing rap groups who had been either swindled or ill-served by their producers and record labels.

Within a few years, Wendy Day realized that if she really wanted to serve hip-hop artists, she would have to do more than break bad deals; she’d have to negotiate better ones. And so, in the mid ’90s, Wendy Day embarked on a quest that would turn a few rappers into self-empowered multi-millionaire entrepreneurs.

She was instrumental in the deal that Master P signed for his label No Limit with Priority Records. She helmed the pact between Creator’s Way and Atlantic Records that The Source called “the best deal in the history of Black music.” She shepherded Eminem into the arms of Dr. Dre. And she was the architect of the stunning distribution deal that Cash Money Records won from Universal Music Group in 1998. The tragedy of Wendy Day’s situation was that she was stiffed on the Cash Money-Universal pact for the first dealmaking fee she ever charged.