“Kentucky Gambler” is a song Dolly wrote based on the story of her Grandpa Parton. As a child, she had been told that her grandfather was quite a gambler. He would go off gambling and lose what little money he had accumulated.
Years later, Merle Haggard would experience that addiction. On several occasions, Haggard lost over $100,000 in a single evening playing blackjack in Nevada casinos. Merle claims that he went through a period in his life where he really thought that he was a professional gambler. He had a tremendous streak of luck that lasted about three years, and had a secret gambling account at the bank that no one knew about. In that account, at its peak, was close to $300,000.
Coincidentally, Dolly’s song “Kentucky Gambler” came along right about the time that Haggard lost the $300,000 in the account, plus another $300,000. The song accurately described the period that Merle was going through.
Haggard first met Dolly when he performed in her hometown of Sevierville, Tennessee in the early 1960s. She was billed as “local talent.” They reunited when Dolly and her Travelin’ Family Band shared the bill with Haggard on a series of show dates in 1974-75. Parton didn’t write “Kentucky Gambler” particularly for Merle, and wasn’t on the road with him when she wrote it, but she happened to be touring with Haggard at the time he recorded the song. As it turned out, Merle became infatuated with Dolly on that series of tours and actually fell in love with her (or so he thought). He composed the song “Always Wanting You” for her, the backstory of which can also be found here on Classic Country Music Stories.