20 NFL Players That Went Completely Broke. The only reason I noticed was that Tiki was pictured, and he was mentioned as 1 of the 20. The list included players who had made bad business decisions after retirement from football, made bad financial decisions, encountered criminal problems,, had relationship problems that turned out to be unbelievably expensive, or a combination of the above. The worst part was that the 20 named were undoubtedly a small percentage of those that could have been named.