But to the New York Times, she is, apparently, an “underdog.” The paper of record used the term twice in its review of her show in a relatively intimate 13,000-seat arena in Louisiana and pulled it out for the headline as well: “On Taylor Swift’s ‘1989’ Tour, the Underdog Emerges as Cool Kid.”
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When Swift was 14, her father relocated to Merrill Lynch’s Nashville office as a way to help dear Taylor break into country music. As a sophomore in high school, she got a convertible Lexus. Around the same time, her dad bought a piece of Big Machine, the label to which Swift signed.

Part of this is because of a critical/journalist school that worships money, popularity and fame: Unlike previous generations of critics, or the traditional journalistic mission to “comfort the afflicted and afflict the comfortable,” Poptimists like the New York Times’ Jon Caramanica don’t buy the old small-is-beautiful premise. And what better way to reconcile the contradiction – to inject a bit of rebel cool into the story – than to make a millionaire daughter of the plutocracy into an underdog?
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Indie rock – and punk and alt-country, and left-of-the-dial R&B and related genres that are uncomfortable with corporations or consumerism – is exactly the kind of thing an offspring of Wall Street like Taylor Swift is not going to respond to. So does her dissing a celebrity ex make her into an underdog? To a poptimist, maybe.