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Smith joins CNN/SI
Stephen A. Smith joins CNN Sports Illustrated, though the network would shut down two years later -
Smith's ESPN Debut
Smith joins ESPN as an analyst for "NBA Shootaround", which would later become "NBA Countdown" -
Smith Begins Hosting His Own Show
Smith began hosting his own show, called "Quite Frankly, with Stephen A. Smith -
Smith Leaves ESPN
Smith announced on his website that he was leaving ESPN, though the exact reason as to why he left is still unknown -
Smith Returns to ESPN
Smith comes back to ESPN as a commentator on First take, as a part of a segment called "Embrace Debate". During this segment, Smith would debate various sports topics against co-commentator Skip Bayless -
Smith Signs Contract with ESPN
Smith signs a contract with ESPN that guarantees him a salary of over three million dollars per year -
Smith Signs Contract Extension
Smith signs a contract extension that keeps him at ESPN for five more years, while earning roughly eight million dollars per year -
Stephen A's World Begins
Smith's newest solo TV show, "Stephen A's World", begins streaming on ESPN's streaming service, ESPN+.