Anna Wintour and Vogue in the 90s

"Amid a blizzard of gossip about an affair and the defection of a key protegee, Vogue's ice queen suddenly seems vulnerable. But for Anna Wintour, maybe that's not all bad—she's just as powerful without the sunglasses." This week's issue is New York Magazine from September 20th, 1999, with Anna Wintour profile "Summer of Her Discontent" by Kevin Gray. Watch this episode on Youtube Watch or listen ad-free on Patreon @WhatsYourIssuePodcast Follow us on Instagram @whatsyourissueshow Learn more about your ad choices. Visit megaphone.fm/adchoices

Episode metadata supplied by the publisher feed · Published May 7, 2026

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Anna Wintour and Vogue in the 90s

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