Last Game: 1999
Who’s Still Paying Him: Los Angeles Express (USFL)
How Much They’re Still Paying Him: 43-year, $40 million contract signed in 1984

OK, the USFL isn’t actually still paying Steve Young. But it could have been—and the bizarre nature of his contract lands him on this list. Here’s the story:

In 1984, Young signed a four-year, $40 million contract with the USFL’s Los Angeles Express. Payments for this contract were slated to go on for 43 years, meaning that they would continue until 2027. But when the league folded and Express owner J. William Oldenberg began experiencing financial issues, Young was given an option with the remaining money on his contract: He could either take $1 million up front or an annuity. Young took the money up front, and probably missed out on millions by doing so.