Age: 29
Albums: From Me To U (2003), What The Game's Been Missing! (2005),

Juelz Santana had it all. He was down with Dipset, he was steadily improving as a rapper, he contributed to classic albums (Diplomatic Immunity, Purple Haze), was on hits (“Oh Boy,” "Hey Ma," "Run It"), and scored his own hits ("There It Go (The Whistle Song)"). He was young, fresh, had street cred, and the girls liked him.

So what if his first two albums weren’t perfect? By 2007, Juelz was poised to break out thanks in part to his excellent Just Blaze-produced single, “The Second Coming.” He was homeboys with the Best Rapper Alive, Lil Wayne (back when he really was the Best Rapper Alive), and they were going to do an album together, I Can’t Feel My Face.

What went wrong? Well, his album Born To Lose, Built To Win was endlessly delayed and has yet to be released. Ditto for his collaborative album with Wayne. Combine that with Dipset’s brief but poorly timed breakup and you’ll see why Santana missed his moment when he could have made a classic.

The saddest part about all this was when, in the midst of the group’s turmoil, Cam’ron called out Santana for being a drug addict. We can’t say that it’s certainly true, but it could explain Santana’s severe lack of productivity. Still, here’s to hoping he can come back like crushed up Adderall cooked crack.

RELATED: The 50 Greatest Dipset Songs