Willie won at cards,
Shared his money and his dick.
Then someone killed him.
"Rambling, Gambling Willie" is an affectionate portrait of a coarse male gambler and slut named Will O'Conley who was good to all the women by whom he got his 27 children. O'Conley had one job, as they say, and he did it well, and then one day a guy blamed him for a bad poker hand and shot him in the head, and that was that for ol' Willie. This song appears on the first volume of the bootleg series, released in 1991, though it was recorded in 1962.
The story of Rambling, Gambling Willie:
Chapter 1: In which we learn of Willie's 27 children by a variety of women, none of whom he married.
Chapter 2: He gambled in the White House and in the rail yards. Wives knew to keep their husbands home when he would roll in to town.
Chapter 3: He held a poker session on the Jackson River Queen when he sailed to New Orleans. By the time they finished the game, he owned the boat.
Chapter 4: He held a week-long game in Cripple Creek, Colorado, with the miners, and when he was done, he owned the town.
Chapter 5: Willie didn't just support his progeny, he gave money to the sick and the poor. He didn't spend much of his money on himself.
Chapter 6: Willie was a good bluffer. Once, he beat a guy with a diamond flush and he didn't even have a pair.
Chapter 7: A guy shot Willie in the head and killed him, thinking Willie was to blame for his bad hand. When Willie took his fall, he was holding aces backed with eights.
Chapter 8: Moral: make your money while you can, because once you pull the dead man's hand, you won't be gambling anymore.