ESPN Rise, Contract Negotiations Regret

Stephen A. Smith has never held back — and in this wide-ranging conversation, he opens up like never before.

From growing up in Hollis, Queens with no heat and little food… to becoming one of the highest-paid figures in sports media… Stephen reflects on the moments that shaped him — the doubts, the losses, the risks, and the relentless work ethic that built his career.

Stephen speaks candidly about grief, fatherhood, ambition, forgiveness, money, and legacy — and what still drives him at 58 years old.