I guess CNN is backing on his current fanbase (mainly teens) staying loyal to him as they graduate from HS and move to college. CNN knows that demographic likely won't have a cable subscription, so this feels like an alternative platform to capture that audience or at least try to. Time will tell if it's a successful strategy.
We'll likely never find out the terms, but I doubt anyone made money out of this deal with the exception possibly of Casey via his new contract with CNN. With over $6m raised, best-case scenario is the investors were made good and the employees walked away with greater long-term certainty and a stable paycheck.
