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How Toby Keith Opened the Door for Taylor Swift’s Big Break

Nearly 20 years ago, the efforts of one country music icon kicked open a door for the arrival of another. In 2005, Toby Keith — who died this week at the age of 62 — entered into a joint venture with music executive Scott Borchetta to launch Big Machine Records, the first record label to sign Taylor Swift. The rest is, quite literally, history.

During Swift’s first-ever television appearance, she strummed the chords and belted out the lyrics to “Teardrops on My Guitar,” the second single from her debut album Taylor Swift, released via Big Machine in 2006. She was 15 years old at the time, sitting in the music room of her high school in Henderson, Tennessee, still in disbelief over the way her life was changing.

“You’re in the room with him and you can feel it, there’s a power there,” Swift told Nashville’s WSMV4 about Keith. “And you’re just like ‘oh my God.’ I don’t think I’ll ever get to a point where I don’t see him and are just like, ‘Oh my God that’s Toby Keith.’”

Keith encountered Swift through Borchetta after DreamWorks Records was dissolved in September 2005. While Keith was focused on getting his own label, Show Dog-Universal Music, off the ground, Borchetta was looking for a stable foundation to build a business partnership with Swift. He had seen her perform in the Bluebird Cafe in Nashville the year prior and didn’t want the opportunity to sign her to slip through his hands. The only problem was that he couldn’t sign her to a label that didn’t exist.

Once Show Dog Nashville was up and running, Keith launched a partnership with Borchetta’s newly-founded Big Machine Records. Swift joined the Big Machine Label Group roster in 2005 and remained there until 2018, years after Show Dog and Big Machine split in 2006. According to the New York Times, Keith continued to own minority positions in Big Machine, along with Swift’s father, Scott Swift.

“Toby’s a really smart businessman,” Borchetta told Forbes in 2013, adding that he knows this mainly because “I send him checks.” In June 2019, Borchetta sold Big Machine — along with the master recordings to Swift’s first six studio albums — to Scooter Braun for a reported $330 million. The sale ignited a major dispute between Swift and her long-time label that resulted in her re-recording all of those albums.

In an interview with the Chicago Tribune in 2016, Keith admitted that he would be able to live off of the money he’s made from Swift’s music for the remainder of his career, even if he never made another album. “No question. I own a piece of the label she’s on,” he explained. “If I just took the royalties I had off of that, I wouldn’t have to do anything else. A bunch of people could live off that.”

Keith released 21 studio albums throughout his career, 11 of which were shared via Show Dog. His most recent release arrived in October 2021. That same year, the musician was diagnosed with stomach cancer. Keith revealed his illness in 2022 but had already been undergoing treatment — including chemotherapy, radiation, and surgery — and dialing back his performance schedule.

Keith’s family confirmed the death on social media Tuesday, writing that the musician “passed peacefully” and was “surrounded by his family.” “He fought his fight with grace and courage,” they wrote.

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He is survived by Tricia Lucus, his wife of 40 years, and their three children.

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