Late country star Toby Keith was not only an uber-talented musician but also a savvy businessman, making him one of the richest artists of his time. While a big chunk of that money came from ventures in the restaurant business, Keith also helped found Big Machine Records, the record label that signed an unknown Taylor Swift and consequentially became one of the industry’s biggest players.

Scott Borchetta, however, is the person credited with the start of Taylor Swift’s career. The story goes that he heard her sing at the Bluebird Café in Nashville, Tennessee, in 2004, and asked her family if she would sign with his label, which he hadn’t established yet. The missing piece, which offered Big Machine Records the infrastructure and financing it needed to get off the ground, was Toby Keith’s Show Dog Nashville label.

According to a Billboard article from 2006, the two labels were structured as “sister companies,” sharing their staff, including Show Dog’s “entire promotion team.” It would be Keith’s efforts and partnership with Borchetta that effectively launched Swift’s career, providing Big Machine Records with the means it needed to support her. In that sense, Keith is definitely responsible for kickstarting her career, but not for discovering her.

Were Taylor Swift and Toby Keith friends?

In an interview from 2005 featuring a young teenage Taylor Swift, the would-be record-breaking musician talked about her partnership with Toby Keith, saying “You’re in the room with him and you can feel it. There’s a power there and you’re just like ‘Oh my god!’” The young artist also confessed she would never stop feeling starstruck by the country star, who passed away too soon on Feb. 6, 2024.

During that period, the two were professional partners and most likely friends, as Swift saw Keith as a mentor and an idol. Shortly after, however, in 2006, Show Dog and Big Machine parted ways, and Keith was no longer an active participant in Swift’s career. He did, however, earn money from her work’s royalties for the rest of his life. Keith reportedly told the Chicago Tribune in 2016 that he could live off of his investment in Borchetta’s label, whose profits came mostly from Swift’s music. “If I just took the royalties from that, I wouldn’t have to do anything else. A bunch of people could live off that,” he said.

It sounds like Keith must have profited from the sale of Big Machine Records to Scooter Braun’s Ithaca Holdings in 2019 and with it the ownership of Swift’s masters, which became the center of a very public dispute between Swift, Borchetta, and Braun. Long distanced from Big Machine, it’s hard to say whether Swift held any remorse for Keith’s involvement in the controversial business deal.

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