When Aretha Franklin died, the IRS said she owed them nearly $8 million. This is a woman who wouldn't sing a single note until somebody counted $25,000 in cash into her hands. She'd sit there with her reading glasses on and watch every bill. Then the cash went in her purse, and the purse went onstage with her and sat on the piano where she could see it all night. It was in her contract, too. The $25,000 had to be handed to Aretha personally, and nobody else on her team could take it unless her office signed off in writing ahead of time. Anything above that could come as a check. That clause is smarter than it looks. It's basically a deposit, the same reason a contractor won't pour your driveway until you've paid something up front. Once a promoter has counted $25,000 into your hands, he's got every reason to make good on the check for the rest. And if he skips town anyway, the money you cared about most is already in your purse. Her friend Tavis Smiley said she came up watching club owners stiff guys like Ray Charles and B.B. King. She wasn't going to let that happen to her, and for decades it didn't. After the show, the band and the backup singers would line up backstage and she'd pay them in cash too. Her agent Dick Alen told her biographer a lot of her staff got paid that way, off the books. Problem is, all of that only protects you from somebody standing in front of you, and the IRS shows up years later with a letter asking for receipts. Back in 1993 the IRS disputed her deductions and she paid over $225,000 in back taxes. Two years later they put a roughly $490,000 lien on her house in Michigan. And during the fight over her estate, a lawyer for one of her sons told the court she'd had no accounting system and once carried $750,000 in uncashed checks around in her purse. The checks were the part she was supposed to be able to trust, and some of them never even made it to a bank. The final bill covered 2010 through 2017, more than $7.8 million once you add interest and penalties. Her estate's lawyer said the fight was really about what counted as income and how much her touring actually cost. Good luck winning either of those arguments without paperwork. So the estate made a deal. The IRS got $800,000 up front and then 45 cents of every dollar her music brought in, mostly royalties and licensing. Another 40 cents sat in escrow for future taxes. For long stretches her sons got nothing. The last payment went through in June 2022. Do the math in her own currency and $7.8 million comes out to 312 of those purse payments. That's the cash from 312 nights of making a promoter count it out in front of her, and her sons still spent almost four years in line behind the IRS.