Terry Bradshaw- $5 million
After retiring from the NFL, Terry invested heavily in real estate. Leading up to the 2008 real estate crash he owned $13 million worth of properties around Texas, Oklahoma, and Mexico. In one interview, Bradshaw admitted that he earned money by “flipping planes” in the same way that some people flip homes. He stated that he often spends $4 or $5 million on a plane before using it for business, and finally selling it again to a new owner for a profit. On his Tv career, Bradshaw earns annually $5 million.