The Taylor Swift silence is quite interesting to me. The fact that she won't even put out a short blurb of condolence speaks volumes.
There are two reasons I can think of for this.
In her 2020 Netflix documentary,
Miss Americana, Taylor indicated that she had been paranoid throughout the 2010s that speaking about politics would ruin her the same way it did the Dixie Chicks. At one point she said, "Throughout my whole career, label executives and publishers would say, ‘don’t be like the Dixie Chicks.'"
Taylor was also a big fan of the Dixie Chicks growing up, and in fact learned to play some of their songs on her guitar while in middle school. It is true that she expressed admiration for Toby Keith in that 2005 news report seen above, and this was well after his feud with the Dixie Chicks. It's possible that 15-year-old Taylor hadn't yet stopped to think about their fall from grace and the politics surrounding it.
However, I think the bigger reason involves Swift's feud with Toby Keith's onetime business partner, Scott Borchetta. As already mentioned in this thread, it was Borchetta who discovered Swift in 2004 and asked to sign her to a record deal. She did eventually sign with him, but the connection to Keith was that he was the co-owner of that label, Big Machine Records.
The real issue came in 2019 when Borchetta sold Big Machine records to a man named Scooter Braun. This horrified Taylor because Scooter was somewhat behind escalating the feud between her and Kim Kardashian, and he had no issue with client Kanye West doing a music video which simulated Taylor being stripped naked. After the news of the sale went public, Taylor went to Tumblr (I bet you didn't think that site still existed) and
blogged about her outrage. Taylor was also upset that Borchetta did not approach her about buying her own music rights back, as she claimed she would have purchased them, clearly having the money to do so at the time.
While Toby Keith had absolutely nothing to do with Borchetta selling Big Machine to Scooter Braun, I have heard around Hollywood that she rested some of the blame at his feet. Toby Keith fell out with Scott Borchetta in 2006, before Taylor was famous, and sold most of his interest in Big Machine. He retained only a minority share and no longer had decision making power. Despite this, Taylor blamed him a little because she felt Borchetta's deal with her was exploitative in the first place. At the time the deal was signed, she had stars in her eyes regarding Toby Keith being a major partner in the label, but as an adult she came to look upon it as them taking advantage of her. Essentially she feared for years that Borchetta would do something awful with the rights she gave to him as a 15-year-old, and 14 years after that, her nightmares came true. For Toby Keith, it was basically guilt by association.
For this reason, it would have surprised me if Taylor put this aside and said something nice in memorial of him. It seems she is taking the position of, "If you do not have anything nice to say, don't say anything at all."
I hope this clears things up for those wondering about the Swift-Keith connection.