Tupac and Biggie were essentially the definition of quintessential rap beef throughout their reigning careers as leaders of the burgeoning hip-hop movement on the East and West coasts alike during the '90s.

Before channeling those differences in their art, Tupac reportedly helped guide the career of The Notorious B.I.G. when he was first getting started.

Addressing the situation in his new book, Original Gangstas: The Untold Story of Dr. Dre, Eazy-E, Ice Cube, Tupac Shakur and the Birth of West Coast Rap, author Ben Westhoff writes that Biggie approached Tupac in the beginning of his career, asking Pac to manage him.

“People forget that Tupac was already blowing up, already a pretty big star when Biggie was just kind of getting started,” Westhoff says in an interview with the Murder Master Music Show.

“Tupac kind of took Biggie under his wing and tried to teach him everything he knew, kind of took him to school,” the author continues. “Biggie’s career wasn’t taking off as fast as he hoped it would. And so he actually asked Tupac if he would be his manager, and Tupac said, ‘No, I think you should stick with Puffy and he’ll get you where you need to be.’”

The fact that Tupac reportedly gave Biggie such advice is really interesting, especially factoring in their history together.

“After he got shot, Tupac believed that Biggie knew about it in advance, knew it was going to happen,” Westhoff adds. “That made him doubly mad because he mentored Biggie so much and helped him, and he really believed that he double-crossed him.”

Check out Westhoff’s interview discussing the two rappers’ relationship in the clip below.