Sill was born in Memphis, Tennessee, to a nightclub owner named Loretta Sill. His father died under mysterious circumstances during a sanitation strike when John was negative four months old. Because the garbage was left undisturbed for weeks, the elder Sill went undiscovered for a long time and any evidence that might have been helpful was completely corrupted. That and the fact that Martin Luther King was assassinated the day of his body’s discovery meant that no one gave a shit. Loretta Sill, formerly a preschool teacher, bought the Regal Club with the insurance money from her husband’s death, the rioting and depression that had followed the civil rights leader’s murder having sent downtown real estate prices into a crazy plummet. And though she had little interest in blues music, or music of any kind, or the serving of drinks, alcoholic or not, she turned out to be a talented businessperson. She bought another club, the Flatted Fifth, then three more, the Hot Spot, Tim’s Place, and the Mother F. When asked why she kept the name of the last, she would feign ignorance and say sweetly, “My, whatever do you mean?” She owned an entire block of Beale Street. She was called the Widow Sill. The Widow Sill did not hate the fact that women worked as prostitutes on her block, but she did very much dislike the idea that anyone else was making money on her block. In short order the Widow Sill had become the Madam Widow Sill, shortened to Mama Widow. The preschool teacher became a racketeer almost overnight.

In contrast to her business life, Loretta Sill’s private life was rather staid, directed, boring. She bought a giant 1900s mansion in Central Gardens, the three-story affair that had been the city retreat of a plantation and slave owner named Rogue LeCou. No one could believe that grand estate was now occupied by the short, slender Black woman who dressed more like Jackie Kennedy than Mahalia Jackson, and her awkward, light-skinned son. This was Memphis.

Young John was sheltered from the dubious action of Beale Street and certainly didn’t know that his mother was the biggest pimp along the Mississippi River. All he knew was that he was rich, homeschooled by private tutors, and then sent off to Phillips Exeter Academy in New Hampshire. It was while he was attending boarding school, rooming with a pudgy, cystic-acne-suffering, rich WASP from the Upper East Side of New York, that he received the news that his mother had been shot to death by a man named Sinbad Willis. John had suspicions growing up that his mother was involved in some shady business ventures. One might have conjectured that the name Sinbad Willis belonged to a rival pimp or a slick gangster from Beale Street, but it instead belonged to the Memphis chief of police.

“Sorry, son,” the overgrown law officer said to the confused seventeen-year-old John Sill. “I went there to serve your mama a warrant for unpaid parking tickets and she met me at the door with a double-barreled shotgun. I’m afraid I panicked and shot her in self-defense.” Twelve times.