How Toby Keith Played a Huge Role in the Rise of Taylor Swift

The pop superstar has yet to speak on the death of her former mentor, business partner and “Courtesy of the Red, White, & Blue” singer

When Toby Keith died Monday night after a two-year battle with stomach cancer at age 62, tributes poured in from Dolly Parton, Carrie Underwood, Jason Aldean, Zach Bryan, Luke Combs and even First Lady Jill Biden. Absent from that list is the other person everyone was talking about this week: Taylor Swift.

The “Bad Blood” singer was no stranger to Keith, who signed Swift to her first record deal in 2005. Then just a teenager still finishing high school, Swift made her first deal with Big Machine Records, into which Keith had just merged his own independent label Show Dog.

Swift had freshly moved to Nashville to pursue her passion, and Keith took an immediate liking to her unique batch of syrupy pop-country songs that would soon make up her debut album, “Taylor Swift.”

In a Nashville-based WSMV-TV clip from that same year, Swift speaks reverently about her new music and business partner, telling the interviewer: “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!’ So I don’t think I’ll ever get to a point where I won’t see him and be like, ‘Oh my God, that’s Toby Keith.’”

The clip was posted Wednesday on X by Matt Couch, founder of conservative blog the DC Patriot, who points out that Swift has yet to say anything about the death of the person who gave her that critical first big break. Messages left with Swift’s publicist were not immediately returned on Wednesday.

While anyone’s first thoughts might turn to a political rift – Keith was once a Democrat who later went independent, fought with the then-Dixie Chicks over “Courtesy of the Red, White & Blue” and eventually played in support of Donald Trump – Swift’s reasons for staying silent on Keith’s death probably run deeper.

When Swift signed to Big Machine, based on Music Row in Nashville, it was a newly forged joint venture between Keith and DreamWorks Records executive Scott Borchetta, distributed by Universal Music Group. Though Keith stepped away from Big Machine early on to focus on his own label, Swift would go on to record seven albums with the label, the last of which was 2017’s “Reputation.”

But Big Machine was bought out in 2019 by Scooter Braun’s company Ithaca Holdings – sparking off the major controversy about ownership of Swift’s master recordings. Swift has since re-recorded much of that music as a rights workaround – in the end, Taylor always wins – but the whole episode was clearly a bitter experience for the now-pop superstar.

Notably, Keith’s name does not appear anywhere on Swift’s official Wikipedia page, aside from one link deep in the references section. That link takes you to a Forbes story from 2013, in which Keith and Borchetta boast about how much money they’ve made from signing Swift eight years prior:

“It was one of the great investments in recent music history,” the article reads. “Borchetta went on to sign Rascal Flatts, Tim McGraw and, most notably, Taylor Swift. Now Keith gets paid whenever Swift does. ‘Toby’s a really smart businessman,’ says Borchetta, who knows because ‘I send him checks.’ How big are the checks that Swift generates for him? ‘I know there’s an extra comma,’ smiles Keith, ‘if you added up all the money I’ve ever made.’”


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