Growing up in Chicago in the 1990's, I saw Mike Ditka on TV every day, pitching one product or another. He had a huge portfolio of endorsement deals in Chicago after he lost his last coaching job in New Orleans and remains an iconic figure in that city.
Indeed, Mike Ditka was going to run for Senate in 2004 against Barack Obama, but declined after learning that he would have to give up his endorsement deals to do so.