The legendary talk-show host could have used his famous suspenders to hold up a wooden barrel. As any journalist will tell you, work in media doesn’t always pay the bills, and Larry King’s first gig in radio was no exception. As a fledgling Miami radio announcer in the 1960s, King made no secret that he was “flying high,” despite the paltry salary that came along with the gig. But his money management troubles came to a head when he was arrested in 1971 and charged with grand larceny for allegedly stealing $5,000 from his business partner, Wall Street financier Louis Wolfson. The charges were eventually dropped, but the dark mark on his career wasn’t, as he was fired from his radio jobs. King wouldn’t hold a regular journalism job for more than four years, dropping him deeper into debt, to the tune of $352,000, and forcing him to declare bankruptcy in 1978. That same year King was offered a late-night talk radio show in Washington, D.C., that eventually became his hugely successful eponymous CNN television show, which ran for 25 years.