Biggie
Puff had massive success in the biz before Biggie even shown up on the scene, the dude was the hottest young exec at the time. Plus Puff also had musical talent, he is a great executive producer and had ear for beats plus direction. It was Puff who decided to give Biggie that polished sound that took his career to another level.
As for Dame, i would say he was starting out in the game and on the same field as Jay. He was managing a couple of niggas, but they didn't have the success of a Jodeci, Mary J,etc. It's like Jay and Dame grew up in the business at the same time, and it was more of a partnership thing, not a boss and employee thing