John Elway

Retired: 1998

Career Earnings: $45.4 million

Est. Net Worth: $145 million

John Elway played NCAA football at Stanford University and was drafted by the Broncos right out of college. Before retirement, he spent sixteen seasons with the Denver team, breaking and setting records as one of the most prolific passers and rushing quarterbacks in the history of the NFL. Elway has started five Super Bowls, a record that has only been broken by Tom Brady.

After retiring, Elway went into business. He co-owned the AFL team, Colorado Crush, until arena football was cancelled in 2008. Currently, John owns four steakhouses and five Cadillac dealerships. Elway also works as a broadcaster for 87.7 The Ticket, a Denver station, during the NFL season.