Childish Gambino's bad investment stems from the NSFL trying to get players to film movies about their careers, or to star in feature films. Little did the players know that the NSFL had worked closely with all the major motion picture studios and worked out fine details in the contracts that the players would need to fund a major portion of said movies. Not knowing the extent of the wording in the contracts, backed on the words of this being "fool proof idea" from agents and financial advisers being paid under the table from the NSFL, many of these players saw their movies flop, and subsequently lost millions. Now, as free agency nears, the NSFL can keep these players hostage as they recycle their lost money in the form of a new contract, all the meanwhile keeping the players completely oblivious to what is happening. Gambino found out after some investigating and the NSFL has threatened to kill his family if he lets word of this get out. Whoops.
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