As he and his team prepare to negotiate another major contract, it seems that Sharpe is well on his way to becoming a Hall of Famer in the sports media world as well.

It's a great time to be in the sports media game as a pundit, especially with names like Stephen A. Smith and Pat McAfee launching the industry into another stratosphere over recent years with their viral takes.

And yet, his most lucrative career may be as a podcaster. Sharpe's media career has taken off since his departure from FS1, thanks in large part to the launch of his Club Shay Sha