WEBVTT 00:00:00.000 --> 00:00:04.080 It is January 23rd, 2026. And I want you to picture 00:00:04.080 --> 00:00:07.540 the fashion industry right now at this very second. 00:00:07.919 --> 00:00:11.939 It feels quiet, doesn't it? A little bit rudderless. 00:00:12.140 --> 00:00:14.460 It really does. It's the silence after a thunderclap. 00:00:14.480 --> 00:00:17.440 We are, what, roughly six months past the moment 00:00:17.440 --> 00:00:20.519 everything changed? June 2025. That was it. The 00:00:20.519 --> 00:00:22.899 moment the tectonic plates shifted. Resignation. 00:00:22.920 --> 00:00:25.940 Anna Wintour steps down. The bob. The sunglasses. 00:00:26.280 --> 00:00:28.800 The dame commander of the British Empire finally 00:00:28.800 --> 00:00:32.070 leaves the building. After 37 years. And I don't 00:00:32.070 --> 00:00:33.869 think we can overstate the magnitude of this. 00:00:34.009 --> 00:00:35.609 I really don't. We aren't just talking about 00:00:35.609 --> 00:00:37.390 an editor leaving a magazine. I mean, editors 00:00:37.390 --> 00:00:39.229 leave magazines all the time. Right. That's just 00:00:39.229 --> 00:00:41.270 business. This is more like the death of a monarch 00:00:41.270 --> 00:00:43.670 or, you know, the collapse of a specific type 00:00:43.670 --> 00:00:46.350 of government. It is the end of an organizing 00:00:46.350 --> 00:00:48.890 principle for the entire industry. It's the end 00:00:48.890 --> 00:00:50.710 of the monarchy of taste. That's what it feels 00:00:50.710 --> 00:00:52.789 like. That is the perfect way to frame it. For 00:00:52.789 --> 00:00:55.429 37 years, Anna Wintour wasn't just reporting 00:00:55.429 --> 00:00:58.649 on fashion. She was, in a very real way, dictating 00:00:58.649 --> 00:01:02.000 the visual language. She was the source code. 00:01:02.259 --> 00:01:05.000 Exactly. She decided what was in and what was 00:01:05.000 --> 00:01:07.560 out with a nod of her head. Or, more likely, 00:01:07.659 --> 00:01:10.219 with a complete absence of a reaction. 37 years. 00:01:10.439 --> 00:01:13.219 It's just, it's a staggering number. I was looking 00:01:13.219 --> 00:01:16.700 at the tenure of Fortune 500 CEOs to compare, 00:01:16.780 --> 00:01:18.659 just to get a sense of the scale here. And what 00:01:18.659 --> 00:01:21.840 did you find? The average tenure for a CEO in 00:01:21.840 --> 00:01:24.780 that bracket is something like 4 .9 years. Wow. 00:01:25.239 --> 00:01:28.329 Yeah. Presidents get four. maybe eight if they're 00:01:28.329 --> 00:01:32.109 lucky. Anna got 37. She outlasted industries. 00:01:32.549 --> 00:01:35.689 She outlasted technologies. She survived everything 00:01:35.689 --> 00:01:38.290 in that time. I think that is the part that fascinates 00:01:38.290 --> 00:01:40.010 me most. I mean, think about the timeline. She 00:01:40.010 --> 00:01:42.750 survived the death of print media, which should 00:01:42.750 --> 00:01:44.510 have been a kill shot. Right there. That should 00:01:44.510 --> 00:01:46.010 have been the end. But then also the rise of 00:01:46.010 --> 00:01:48.750 the Internet, the influencer economy, the 2008 00:01:48.750 --> 00:01:51.670 recession, which just decimated luxury spending. 00:01:51.849 --> 00:01:54.390 And the 2020 racial reckoning, which took down 00:01:54.390 --> 00:01:56.980 a lot of her peers. She just she outlasted. everyone. 00:01:57.140 --> 00:02:00.359 So here is the mission for this deep dive. We 00:02:00.359 --> 00:02:03.359 have a massive stack of sources here. The detailed 00:02:03.359 --> 00:02:06.120 biographical dossiers, the Condé Nast financial 00:02:06.120 --> 00:02:09.960 reports, the devil wears Prada cultural analysis, 00:02:10.099 --> 00:02:12.060 and of course, all the coverage of her exit last 00:02:12.060 --> 00:02:15.280 year. We're going to look past the meme. We have 00:02:15.280 --> 00:02:17.560 to. Right. Because if you only know her from 00:02:17.560 --> 00:02:20.099 the Meryl Streep movie or the GIFs on Twitter, 00:02:20.300 --> 00:02:23.740 you know the caricature. You know the ice queen. 00:02:23.979 --> 00:02:26.460 You know the difficult boss who throws her coat 00:02:26.460 --> 00:02:28.680 at her assistant. And that's a fun character, 00:02:28.840 --> 00:02:31.199 but it's not the whole story. I want to know 00:02:31.199 --> 00:02:33.199 the executive. I want to know the business mechanics 00:02:33.199 --> 00:02:36.199 of how a single woman accumulates that much power 00:02:36.199 --> 00:02:39.400 and holds onto it for nearly four decades in 00:02:39.400 --> 00:02:41.810 an industry famous for being you know, incredibly 00:02:41.810 --> 00:02:43.550 fickle. Then we have to look at the machinery 00:02:43.550 --> 00:02:45.909 she built. This is a story about the professionalization 00:02:45.909 --> 00:02:48.550 of an entire industry. I mean, before Anna, fashion 00:02:48.550 --> 00:02:50.849 was, well, it was a hobby for the rich, a little 00:02:50.849 --> 00:02:53.830 bit of a cottage industry. Exactly. After Anna, 00:02:53.909 --> 00:02:56.969 it was a multi -trillion dollar global entertainment 00:02:56.969 --> 00:03:00.009 complex. That's the shift. But to understand 00:03:00.009 --> 00:03:02.289 the machine, we have to understand the architect. 00:03:02.830 --> 00:03:05.250 And looking at the early biographical data you 00:03:05.250 --> 00:03:07.469 pulled, I was struck by one thing immediately. 00:03:08.650 --> 00:03:12.150 We love a rags -to -riches story in fashion. 00:03:12.569 --> 00:03:14.969 You know, we love the I was sewing hems in a 00:03:14.969 --> 00:03:17.969 basement narrative. And this is decidedly not 00:03:17.969 --> 00:03:19.969 that. Not even close. It's the opposite of that. 00:03:20.030 --> 00:03:22.270 No. If you want to understand Anna Wintour's 00:03:22.270 --> 00:03:24.590 management style in 2025, you have to go back 00:03:24.590 --> 00:03:27.530 to London, 1949. She wasn't born into fashion. 00:03:27.590 --> 00:03:30.330 She was born into media royalty. Her father is 00:03:30.330 --> 00:03:33.810 Charles Wintour. And in the sources, he's described 00:03:33.810 --> 00:03:36.599 as a titan of Fleet Street. He was the editor 00:03:36.599 --> 00:03:39.000 of the Evening Standard, a legend in his own 00:03:39.000 --> 00:03:41.439 right. They called him Chili Charlie. Chili Charlie. 00:03:41.599 --> 00:03:44.560 So the emotional temperature, that sort of ice 00:03:44.560 --> 00:03:47.080 queen demeanor, might be genetic. It appears 00:03:47.080 --> 00:03:49.680 so. But Charles is the key to the whole operation. 00:03:49.860 --> 00:03:52.080 He wasn't just a newspaper man. He was a brutally 00:03:52.080 --> 00:03:54.479 efficient editor. He understood the business 00:03:54.479 --> 00:03:57.060 of attention long before we had algorithms to 00:03:57.060 --> 00:03:59.699 measure it. And he taught Anna a specific lesson 00:03:59.699 --> 00:04:03.310 about relevance when she was still a child. This 00:04:03.310 --> 00:04:04.889 is the part of the story that I think sets the 00:04:04.889 --> 00:04:07.349 entire stage. I found this detail fascinating. 00:04:07.509 --> 00:04:09.449 We're talking about the swinging 60s in London. 00:04:09.629 --> 00:04:12.330 I mean, you've got the Beatles, the Stones, Mary 00:04:12.330 --> 00:04:15.669 Quant. The culture is just exploding. And Charles 00:04:15.669 --> 00:04:18.290 Wintour is sitting there running this very serious 00:04:18.290 --> 00:04:20.769 newspaper, but he's obsessed with the youth market. 00:04:20.990 --> 00:04:23.750 He saw the demographic shift before anyone else. 00:04:23.910 --> 00:04:26.970 He was a numbers guy underneath it all. He realized 00:04:26.970 --> 00:04:30.600 that the post -war generation, the boomers, We're 00:04:30.600 --> 00:04:32.759 going to control the economy. So he did something 00:04:32.759 --> 00:04:35.500 very Anna. He didn't guess what they wanted. 00:04:35.779 --> 00:04:37.660 He went to the source. You went to the source. 00:04:37.759 --> 00:04:39.939 He treated his teenage daughter like a focus 00:04:39.939 --> 00:04:42.480 group. Imagine that dynamic at the dinner table. 00:04:42.620 --> 00:04:44.779 You're 15 years old eating your peas and your 00:04:44.779 --> 00:04:48.230 dad. Chili Charlie asks, how do we structure 00:04:48.230 --> 00:04:51.170 the layout to appeal to the 16 to 24 demographic? 00:04:51.629 --> 00:04:54.050 But she answered and he listened. That's the 00:04:54.050 --> 00:04:56.209 other part of it. He actually added a column 00:04:56.209 --> 00:04:58.430 to the evening standard based on her advice about 00:04:58.430 --> 00:05:00.689 what young people were actually doing, listening 00:05:00.689 --> 00:05:03.470 to and wearing in London. So this is the first 00:05:03.470 --> 00:05:06.670 nugget of the Wintour playbook. Don't judge the 00:05:06.670 --> 00:05:09.810 youth. Monetize them. Understand them as a market 00:05:09.810 --> 00:05:12.600 force. While other aristocratic parents were 00:05:12.600 --> 00:05:15.360 probably horrified by the 60s counterculture, 00:05:15.480 --> 00:05:17.920 you know, the long hair and the loud music. Charles 00:05:17.920 --> 00:05:19.860 Wintour was trying to figure out how to sell 00:05:19.860 --> 00:05:23.560 ad space against it. Precisely. And Anna absorbed 00:05:23.560 --> 00:05:26.779 that lesson completely. She saw that cool wasn't 00:05:26.779 --> 00:05:29.850 just an aesthetic, it was a... currency. And 00:05:29.850 --> 00:05:32.129 I mean, let's be honest, she had the pedigree 00:05:32.129 --> 00:05:34.110 to back it up. Oh, absolutely. This wasn't a 00:05:34.110 --> 00:05:36.329 middle class kid trying to break in. No, we're 00:05:36.329 --> 00:05:38.370 talking about a family tree that includes a prime 00:05:38.370 --> 00:05:41.029 minister and the Earl of Bristol. Her great, 00:05:41.089 --> 00:05:43.389 great, great grandmother was the Duchess of Devonshire. 00:05:43.829 --> 00:05:47.269 This is old, old English aristocracy. And that 00:05:47.269 --> 00:05:49.149 gives you a certain kind of confidence, doesn't 00:05:49.149 --> 00:05:51.709 it? The kind of heavy upper crust British confidence 00:05:51.709 --> 00:05:54.110 where you don't feel the need to raise your voice 00:05:54.110 --> 00:05:56.410 because you just assume everyone is already listening. 00:05:56.730 --> 00:05:58.910 It's the confidence of someone who has never 00:05:58.910 --> 00:06:01.189 once in their life worried about paying rent. 00:06:01.569 --> 00:06:03.850 But, and this is the twist in the story, she 00:06:03.850 --> 00:06:06.790 was a rebel. The Bob. The Bob. She started wearing 00:06:06.790 --> 00:06:09.670 that hair at age 14. That is just wild to me. 00:06:09.709 --> 00:06:11.829 Who has their personal brand locked in at 14? 00:06:12.050 --> 00:06:15.189 I had braces and a terrible perm at 14. It's 00:06:15.189 --> 00:06:18.589 a visual declaration of consistency. In a world 00:06:18.589 --> 00:06:22.110 of chaos, and the 60s were chaotic, she created 00:06:22.110 --> 00:06:25.529 a uniform for herself. A logo. She was attending 00:06:25.529 --> 00:06:27.949 North London Collegiate School, which is very 00:06:27.949 --> 00:06:30.410 prestigious, very rigid. And she's there taking 00:06:30.410 --> 00:06:32.889 up her hemlines, you know, constantly skirting 00:06:32.889 --> 00:06:34.870 the dress code. But it's interesting. She wasn't 00:06:34.870 --> 00:06:37.209 rebelling to be a hippie. She wasn't dropping 00:06:37.209 --> 00:06:39.949 out to join a commune. She was rebelling to be 00:06:39.949 --> 00:06:43.269 chic. Exactly. She wasn't burning the establishment 00:06:43.269 --> 00:06:46.790 down. She was restyling it from within. And this 00:06:46.790 --> 00:06:49.129 leads to the most controversial part of her education 00:06:49.129 --> 00:06:51.889 or, well, strictly speaking, the end of it. The 00:06:51.889 --> 00:06:55.089 dropout. This is a crucial pivot point in her 00:06:55.089 --> 00:06:57.610 biography. She leaves North London Collegiate. 00:06:57.970 --> 00:07:00.529 Her parents enroll her in a fashion training 00:07:00.529 --> 00:07:03.129 program at Harrods. Harrods. I mean, that is 00:07:03.129 --> 00:07:05.430 the pinnacle of British retail luxury. If you 00:07:05.430 --> 00:07:07.089 want to learn the trade, you go to Harrods. It's 00:07:07.089 --> 00:07:09.250 like going to Harvard for business. And she quits. 00:07:09.250 --> 00:07:11.589 But she doesn't just quit because it's hard or 00:07:11.589 --> 00:07:15.170 boring. She quits with a thesis statement, a 00:07:15.170 --> 00:07:17.529 declaration. You either know fashion or you don't. 00:07:17.529 --> 00:07:19.759 You either know fashion or you don't. I want 00:07:19.759 --> 00:07:21.779 to pause on that for a second, because that is 00:07:21.779 --> 00:07:23.699 an incredibly dangerous idea. It's arrogant. 00:07:23.959 --> 00:07:26.360 It's unbelievably arrogant for a teenager. It 00:07:26.360 --> 00:07:28.319 is, but it's also the foundation of her entire 00:07:28.319 --> 00:07:31.899 career. She is rejecting the idea that taste 00:07:31.899 --> 00:07:34.459 is a skill you learn, like accounting or coding. 00:07:34.680 --> 00:07:37.259 She's making the argument that taste is an instinct. 00:07:37.379 --> 00:07:40.220 You have the gene or you don't. Which implies 00:07:40.220 --> 00:07:43.399 that she believed, at roughly 16 years old, that 00:07:43.399 --> 00:07:45.500 she already knew more than the people teaching 00:07:45.500 --> 00:07:48.459 the course at Harrods. She bet on her own eye. 00:07:48.939 --> 00:07:52.339 And her father, Chili Charlie, again, he facilitates 00:07:52.339 --> 00:07:54.360 this. He doesn't force her back to school. He 00:07:54.360 --> 00:07:56.540 gets on the phone and arranges her first job. 00:07:56.680 --> 00:07:59.540 At Biba. At Biba. And for our listeners who might 00:07:59.540 --> 00:08:02.560 not be deep into 60s fashion history, Biba wasn't 00:08:02.560 --> 00:08:05.620 just a store. It was a scene. Biba was ground 00:08:05.620 --> 00:08:08.310 zero for swinging London. Biba was where the 00:08:08.310 --> 00:08:10.189 Rolling Stones hung out. It was dark. It was 00:08:10.189 --> 00:08:12.149 moody. It sold a lifestyle. It was the first 00:08:12.149 --> 00:08:14.410 lifestyle brand before that term even existed. 00:08:14.629 --> 00:08:17.550 So working at Biba at 15 is like working at Apple 00:08:17.550 --> 00:08:21.769 in 1980 or maybe OpenAI in 2023. Yeah. You were 00:08:21.769 --> 00:08:24.110 at the center of the blast radius of culture. 00:08:24.370 --> 00:08:26.670 She's just absorbing this atmosphere. And she 00:08:26.670 --> 00:08:28.670 moves into magazines really quickly after that. 00:08:28.730 --> 00:08:31.350 She lands at Harper's and Queen. And she's already 00:08:31.350 --> 00:08:33.850 calling her shot. The ambition is just baked 00:08:33.850 --> 00:08:36.029 in from day one. She told everyone who would 00:08:36.029 --> 00:08:38.929 listen, all her coworkers, I want to edit Vogue. 00:08:38.990 --> 00:08:41.169 Not I want to be a writer. Not I want to be a 00:08:41.169 --> 00:08:45.009 stylist. She wanted the big chair from the very 00:08:45.009 --> 00:08:47.330 beginning. But ambition alone doesn't get you 00:08:47.330 --> 00:08:49.990 there. You need resilience. And that's why we 00:08:49.990 --> 00:08:53.850 have to talk about 1975, New York City, Harper's 00:08:53.850 --> 00:08:56.809 Bazaar. The failure. The first big one. She gets 00:08:56.809 --> 00:09:00.389 fired. After just nine months. The editor at 00:09:00.389 --> 00:09:03.269 the time, Tony Mazzola. fires her. And the reason 00:09:03.269 --> 00:09:05.289 he gave is just fascinating, especially given 00:09:05.289 --> 00:09:07.629 what we know now. He said her photo shoots were 00:09:08.059 --> 00:09:10.460 Too innovative. Too innovative. Yeah. How can 00:09:10.460 --> 00:09:12.799 you possibly be too innovative in fashion? Isn't 00:09:12.799 --> 00:09:14.820 that the whole point? Well, you have to look 00:09:14.820 --> 00:09:16.500 at what she was doing. Harper's Bazaar at the 00:09:16.500 --> 00:09:19.059 time was very conventional, very polite, very 00:09:19.059 --> 00:09:21.620 safe. Anna was coming in and putting models in 00:09:21.620 --> 00:09:24.059 dreadlocks. She was shooting in gritty outdoor 00:09:24.059 --> 00:09:26.620 locations. She was using harsh lighting. She 00:09:26.620 --> 00:09:29.200 was breaking all the visual rules of the 1970s. 00:09:29.200 --> 00:09:31.419 So she was trying to drag the magazine into the 00:09:31.419 --> 00:09:33.759 future. And the magazine just wasn't ready to 00:09:33.759 --> 00:09:36.480 go with her. Right. But for a high achiever, 00:09:36.559 --> 00:09:38.980 getting fired is usually the moment that makes 00:09:38.980 --> 00:09:41.279 or breaks them. Most people would retreat. They'd 00:09:41.279 --> 00:09:43.080 go back to London with their tail between their 00:09:43.080 --> 00:09:45.720 legs. They'd say New York is too hard. And it 00:09:45.720 --> 00:09:49.919 goes to Viva. Yes. Yes. Viva. I'd look up Viva. 00:09:49.919 --> 00:09:53.000 This is an unexpected career move. It was owned 00:09:53.000 --> 00:09:55.980 by Bob Guccione, the guy who founded Penthouse. 00:09:56.490 --> 00:09:58.710 It was an adult magazine for women. That's the 00:09:58.710 --> 00:10:01.409 most polite way to put it. It was risque. So 00:10:01.409 --> 00:10:03.370 the future Dame Commander of the British Empire 00:10:03.370 --> 00:10:06.570 is working for a softcore porn publisher. She 00:10:06.570 --> 00:10:09.169 was. But here's the thing. She treated it like 00:10:09.169 --> 00:10:11.590 it was the New York Times. This is the grit that 00:10:11.590 --> 00:10:13.710 people miss when they only see the Ice Queen. 00:10:14.129 --> 00:10:16.210 She didn't turn up her nose at the work. She 00:10:16.210 --> 00:10:19.429 saw an opportunity. A huge one. Viva had a massive 00:10:19.429 --> 00:10:21.879 budget. thanks to Guccione's publishing empire. 00:10:22.159 --> 00:10:25.279 So she used that money to hire the best photographers, 00:10:25.480 --> 00:10:28.340 the best stylists. She produced these incredible 00:10:28.340 --> 00:10:31.129 high fashion shoots for a girly mag. That is 00:10:31.129 --> 00:10:33.470 such a strategic flex. It's like she's saying, 00:10:33.570 --> 00:10:36.049 I don't care about the platform. I care about 00:10:36.049 --> 00:10:38.490 the budget and the creative control. And she 00:10:38.490 --> 00:10:40.730 got her first personal assistant there. She started 00:10:40.730 --> 00:10:43.889 building the structure of the boss. She learned 00:10:43.889 --> 00:10:46.169 that if you produce excellence, people eventually 00:10:46.169 --> 00:10:48.649 stop caring about where it was published. She 00:10:48.649 --> 00:10:50.830 was laundering her reputation through the sheer 00:10:50.830 --> 00:10:53.269 quality of her work. Which sets the stage for 00:10:53.269 --> 00:10:55.649 the 80s. She claws her way back to the mainstream. 00:10:56.009 --> 00:11:00.220 She lands at New York Magazine in 1981. And this 00:11:00.220 --> 00:11:02.000 is where I think the Wintour formula actually 00:11:02.000 --> 00:11:05.340 coalesces into a business strategy. This is the 00:11:05.340 --> 00:11:08.220 moment. Absolutely. At New York Magazine, she 00:11:08.220 --> 00:11:10.039 wasn't just doing fashion spreads in the back 00:11:10.039 --> 00:11:11.899 of the book. She was looking at the whole package, 00:11:12.120 --> 00:11:14.519 especially the cover strategy. And she noticed 00:11:14.519 --> 00:11:17.159 something that seems so obvious to us now. But 00:11:17.159 --> 00:11:19.480 at the time. was apparently revolutionary. The 00:11:19.480 --> 00:11:22.159 power of the celebrity. Before this, magazine 00:11:22.159 --> 00:11:25.899 covers were almost always models. Nameless, beautiful 00:11:25.899 --> 00:11:28.200 mannequins. Right. And I realized that if you 00:11:28.200 --> 00:11:30.440 put an actress on the cover or a famous socialite, 00:11:30.519 --> 00:11:33.080 someone the audience recognized and had a relationship 00:11:33.080 --> 00:11:36.620 with, the newsstand sales spiked. It wasn't about 00:11:36.620 --> 00:11:38.720 the clothes anymore. It was about the person 00:11:38.720 --> 00:11:41.100 wearing the clothes. Yeah. The narrative. It 00:11:41.100 --> 00:11:42.840 was the beginning of the culture of personality 00:11:42.840 --> 00:11:46.639 that defines our media landscape today. She understood 00:11:46.639 --> 00:11:48.379 that people didn't just want to see the dress. 00:11:48.440 --> 00:11:50.539 They wanted to see the life of the person in 00:11:50.539 --> 00:11:53.059 the dress. It was aspirational in a whole new 00:11:53.059 --> 00:11:56.019 way. And she rode that insight all the way to 00:11:56.019 --> 00:11:58.559 her now famous interview with Grace Mirabella. 00:11:58.700 --> 00:12:01.019 The audacity of this moment is breathtaking. 00:12:01.769 --> 00:12:04.190 Just picture it. Grace Mirabella is the sitting 00:12:04.190 --> 00:12:06.370 editor -in -chief of Vogue. She is the queen. 00:12:06.769 --> 00:12:09.970 She grants Anna an interview, probably as a favor 00:12:09.970 --> 00:12:12.509 to someone. And she asks a pretty standard interview 00:12:12.509 --> 00:12:15.470 question. What job do you want here? And Anna, 00:12:15.549 --> 00:12:18.190 without blinking, says, I want your job. Your 00:12:18.190 --> 00:12:21.090 job. To her face. I mean, imagine the silence 00:12:21.090 --> 00:12:23.009 in that room. It's like walking into a final 00:12:23.009 --> 00:12:25.409 round interview and telling the CEO, I'm here 00:12:25.409 --> 00:12:27.529 to pack your boxes. But here's the thing about 00:12:27.529 --> 00:12:30.809 Condé Nast at that time, especially under CNewhouse. 00:12:31.330 --> 00:12:34.789 They didn't see that as insubordination. They 00:12:34.789 --> 00:12:38.429 saw it as hunger. Condé Nast thrived on that 00:12:38.429 --> 00:12:40.889 Shark Tank energy. They loved it. They loved 00:12:40.889 --> 00:12:43.789 it so much, they started a bidding war to get 00:12:43.789 --> 00:12:47.190 her. They made her the first ever creative director 00:12:47.190 --> 00:12:51.940 of U .S. Vogue. in 83, doubled her salary. But 00:12:51.940 --> 00:12:53.940 she still had to prove she could actually run 00:12:53.940 --> 00:12:55.759 a team, run a whole magazine, so they shipped 00:12:55.759 --> 00:12:58.379 her back to London. A trial run. They sent her 00:12:58.379 --> 00:13:00.460 to run British Vogue, and this is where the nuclear 00:13:00.460 --> 00:13:03.059 wind tour legend really begins. Because she didn't 00:13:03.059 --> 00:13:04.899 go back to London to make friends or, you know, 00:13:04.899 --> 00:13:07.080 have a nice cup of tea. No. She went back to 00:13:07.080 --> 00:13:10.820 clean house. She fired longtime staff. She terrorized 00:13:10.820 --> 00:13:13.539 the copy department. She wanted to Americanize 00:13:13.539 --> 00:13:15.580 British Vogue. What does that mean exactly, to 00:13:15.580 --> 00:13:17.370 Americanize it? What was she changing? Well, 00:13:17.470 --> 00:13:20.070 British Vogue was very eccentric. It was about 00:13:20.070 --> 00:13:22.809 aristocracy, English roses in a garden, country 00:13:22.809 --> 00:13:26.250 weekends. It was slow. It was polite. Anna wanted 00:13:26.250 --> 00:13:28.690 it to be fast. She wanted it to be about careers, 00:13:28.889 --> 00:13:31.710 money, sex and power. She basically introduced 00:13:31.710 --> 00:13:34.730 the concept of the working woman to the pages 00:13:34.730 --> 00:13:37.450 of British Vogue. But not just any working woman, 00:13:37.629 --> 00:13:40.029 the executive woman, the woman who wants the 00:13:40.029 --> 00:13:44.440 corner office. But then she stumbles. And I think 00:13:44.440 --> 00:13:46.480 this is the most overlooked part of her resume 00:13:46.480 --> 00:13:49.879 because it was a huge public failure. We have 00:13:49.879 --> 00:13:52.279 to talk about House and Garment. House and Garden, 00:13:52.419 --> 00:13:56.519 or as the industry very cruelly mocked it, Vanity 00:13:56.519 --> 00:14:00.740 Chair. This was 1987. Condé Nast gives her this 00:14:00.740 --> 00:14:04.240 Heritage Interior Design magazine. And she basically 00:14:04.240 --> 00:14:06.259 tries to turn it into vogue with furniture. She 00:14:06.259 --> 00:14:09.000 did. She put fashion models into living rooms. 00:14:09.120 --> 00:14:11.080 She put celebrities on the cover. She made it 00:14:11.080 --> 00:14:13.460 about the style of the homeowner, not the wallpaper 00:14:13.460 --> 00:14:16.879 or the architecture. And the readers, the traditional 00:14:16.879 --> 00:14:19.059 loyal subscribers, hated it. They didn't just 00:14:19.059 --> 00:14:21.399 hate it. They canceled their subscriptions in 00:14:21.399 --> 00:14:24.460 droves. They called the office screaming. Advertisers 00:14:24.460 --> 00:14:26.720 started pulling out. By all metrics, it was a 00:14:26.720 --> 00:14:29.250 commercial disaster. It was. She fundamentally 00:14:29.250 --> 00:14:31.690 misread the room. She thought her taste was universal. 00:14:31.889 --> 00:14:33.730 She thought, if I like it, everyone will like 00:14:33.730 --> 00:14:36.450 it. But the interior design demographic is different. 00:14:36.529 --> 00:14:38.850 They want the details. They want the specs. They 00:14:38.850 --> 00:14:40.929 didn't want a model graping herself over a sofa. 00:14:40.990 --> 00:14:42.850 They wanted to know where the fabric on the sofa 00:14:42.850 --> 00:14:45.450 came from and how much it cost per yard. So why 00:14:45.450 --> 00:14:48.309 didn't she get fired? I mean, if I lose a company 00:14:48.309 --> 00:14:51.590 millions of dollars in ad revenue and alienate 00:14:51.590 --> 00:14:53.990 the core customer base, I'm clearing out my desk. 00:14:54.269 --> 00:14:56.549 This is the ultimate lesson in corporate politics. 00:14:57.179 --> 00:15:00.279 The Condé Nast executives see Newhouse specifically. 00:15:00.659 --> 00:15:02.799 They didn't care that much about the house and 00:15:02.799 --> 00:15:05.120 garden balance sheet. They cared that she was 00:15:05.120 --> 00:15:07.460 shaking things up. They saw the house and garment 00:15:07.460 --> 00:15:10.600 disaster not as a failure of taste, but as a 00:15:10.600 --> 00:15:12.799 proof of concept that she was willing to break 00:15:12.799 --> 00:15:15.460 things. So the failure actually proves she had 00:15:15.460 --> 00:15:18.279 the guts to take over the flagship magazine Vogue. 00:15:18.649 --> 00:15:20.690 Exactly. It showed she wouldn't be sentimental. 00:15:21.049 --> 00:15:23.830 It showed she wasn't afraid to alienate people 00:15:23.830 --> 00:15:26.710 in pursuit of a vision. Ten months later, despite 00:15:26.710 --> 00:15:29.149 the disaster, they handed her the keys to the 00:15:29.149 --> 00:15:32.629 kingdom. November 1988. She becomes editor -in 00:15:32.629 --> 00:15:34.809 -chief of American Vogue. And the very first 00:15:34.809 --> 00:15:37.629 thing she does... is kill the close -up headshot. 00:15:37.789 --> 00:15:39.730 We really have to set the scene for Vogue pre 00:15:39.730 --> 00:15:41.830 -Anna. Under Grace Marabella, the covers were 00:15:41.830 --> 00:15:43.909 very, very specific. They were tight headshots 00:15:43.909 --> 00:15:47.029 of famous models, lots of makeup, very studio 00:15:47.029 --> 00:15:49.970 -lit. The word everyone used was beige. Beige. 00:15:50.009 --> 00:15:52.230 Not a great word for a fashion magazine. No. 00:15:52.389 --> 00:15:54.690 It was successful, but it was boring. It was 00:15:54.690 --> 00:15:57.230 predictable. And it was losing ground to a new 00:15:57.230 --> 00:15:59.990 magazine called Elle, which was younger, fresher, 00:16:00.110 --> 00:16:03.110 and more energetic. So Anna walks in. November 00:16:03.110 --> 00:16:06.940 1988. Her very first cover. It's the model Michaela 00:16:06.940 --> 00:16:10.100 Bricue. And this single image changes the entire 00:16:10.100 --> 00:16:12.720 business logic of fashion media. Describe it 00:16:12.720 --> 00:16:15.580 for us. Because if you just look at it now, in 00:16:15.580 --> 00:16:19.120 2026, it looks... Well, it looks normal. But 00:16:19.120 --> 00:16:22.559 in 1988, it was completely alien. So you have 00:16:22.559 --> 00:16:24.740 Michaela Brickhew, a 19 -year -old Israeli model. 00:16:25.000 --> 00:16:27.039 First off, she's not in a studio. She's outside 00:16:27.039 --> 00:16:29.320 on a street. There's natural light hitting her 00:16:29.320 --> 00:16:31.399 face. Her eyes are half closed, like she's in 00:16:31.399 --> 00:16:33.120 the middle of a laugh or squinting in the sun. 00:16:33.379 --> 00:16:35.340 Her hair is blowing across her face. It looks 00:16:35.340 --> 00:16:37.039 like a snapshot, like her friend took it. It 00:16:37.039 --> 00:16:38.860 does. It feels accidental. But the revolution 00:16:38.860 --> 00:16:41.659 is the outfit. On top, she is wearing a Christian 00:16:41.659 --> 00:16:44.200 Lacroix jacket. This is haute couture. It is 00:16:44.200 --> 00:16:46.019 completely covered in jewels. It has a giant 00:16:46.019 --> 00:16:48.879 cross on the front. It costs $10 ,000. A total 00:16:48.879 --> 00:16:51.879 fortune in 1988 dollars. And she is wearing it 00:16:51.879 --> 00:16:55.899 with a $50 pair of faded light wash guest jeans. 00:16:56.240 --> 00:16:59.299 High and low. The sacred and the profane together. 00:16:59.519 --> 00:17:01.779 This broke every rule in the book. You did not 00:17:01.779 --> 00:17:04.859 put denim on the cover of American Vogue. Denim 00:17:04.859 --> 00:17:07.079 was for laborers or teenagers on the weekend. 00:17:07.440 --> 00:17:10.279 Couture was for the ballroom and a smash them 00:17:10.279 --> 00:17:12.220 together in one image. And the printers actually 00:17:12.220 --> 00:17:14.160 called the office, right? I love this detail. 00:17:14.359 --> 00:17:16.759 They did. They called the Vogue offices and said. 00:17:17.259 --> 00:17:19.039 We think there's been a mistake with the film. 00:17:19.140 --> 00:17:21.380 You sent us the proofing sheet, not the final 00:17:21.380 --> 00:17:24.160 cover. They genuinely thought it was an outtake. 00:17:24.200 --> 00:17:26.259 They couldn't believe it was the intended image. 00:17:26.579 --> 00:17:29.940 But why was this such a paradigm shift? I mean, 00:17:29.960 --> 00:17:32.960 beyond just it looked cool, what was the business 00:17:32.960 --> 00:17:35.700 idea behind it? Because it democratized the aspiration. 00:17:36.039 --> 00:17:38.519 It sent a message. You don't have to buy the 00:17:38.519 --> 00:17:40.599 $10 ,000 jacket to be part of this world. You 00:17:40.599 --> 00:17:43.079 probably already own the jeans. It acknowledged 00:17:43.079 --> 00:17:46.039 how real women, even wealthy women, actually 00:17:46.039 --> 00:17:48.940 dress. They mixed things. It moved fashion from 00:17:48.940 --> 00:17:51.299 the pedestal of the studio to the reality of 00:17:51.299 --> 00:17:54.039 the street. And Wintour, looking back on it, 00:17:54.160 --> 00:17:56.220 she claimed this wasn't some grand intellectual 00:17:56.220 --> 00:17:58.859 statement. No, her explanation was much simpler. 00:17:59.259 --> 00:18:01.400 She said the couture jacket was actually part 00:18:01.400 --> 00:18:03.720 of a suit, but Michaela had gained a little weight 00:18:03.720 --> 00:18:06.000 on vacation and the skirt didn't fit. So the 00:18:06.000 --> 00:18:07.940 stylist just threw on the jean that she was already 00:18:07.940 --> 00:18:09.839 wearing. So it was an accident. A happy accident. 00:18:10.940 --> 00:18:13.640 Wintour said she just sensed the winds of change. 00:18:13.880 --> 00:18:16.200 Again, it comes back to that instinct. She wasn't 00:18:16.200 --> 00:18:18.619 analyzing data. She was feeling the cultural 00:18:18.619 --> 00:18:21.619 shift. She knew the stiffness of the 80s was 00:18:21.619 --> 00:18:24.500 dying and the casual luxury of the 90s was about 00:18:24.500 --> 00:18:27.839 to be born. So she secures her throne, she revolutionizes 00:18:27.839 --> 00:18:30.640 the cover, and she starts this decades -long 00:18:30.640 --> 00:18:33.619 reign. But now we have to talk about the myth. 00:18:33.980 --> 00:18:36.420 Because for millions of people around the world, 00:18:36.579 --> 00:18:39.759 Anna Wintour isn't a person. She is Miranda Priestly. 00:18:40.140 --> 00:18:42.119 The Devil Wears Prada, the book that changed 00:18:42.119 --> 00:18:45.079 everything. The book comes out in 2003. Lauren 00:18:45.079 --> 00:18:47.579 Weisberger, one of her former assistants, writes 00:18:47.579 --> 00:18:50.500 this thinly -veiled romantic clef. Then the movie 00:18:50.500 --> 00:18:53.700 follows in 2006. Meryl Streep gives this iconic 00:18:53.700 --> 00:18:56.660 Oscar -nominated performance. And suddenly, Anna 00:18:56.660 --> 00:18:59.119 Wintour is the global symbol of the tyrannical 00:18:59.119 --> 00:19:02.720 boss. It is a rare thing when a pop culture caricature 00:19:02.720 --> 00:19:05.259 becomes more famous than the person it is based 00:19:05.259 --> 00:19:08.319 on. Miranda Priestly is demanding. She's impossible 00:19:08.319 --> 00:19:12.160 to please. She humiliates people for sport. That's 00:19:12.160 --> 00:19:15.579 all. But Anna. Yeah. She did something brilliant. 00:19:15.740 --> 00:19:18.819 She didn't sue. She didn't hide. She didn't issue 00:19:18.819 --> 00:19:21.079 a statement. She went to the premiere. And she 00:19:21.079 --> 00:19:23.400 was dressed head to toe in Prada. It is the ultimate 00:19:23.400 --> 00:19:26.200 power move. By attending the premiere wearing 00:19:26.200 --> 00:19:28.720 the brand mentioned in the title, she signaled 00:19:28.720 --> 00:19:31.740 to the entire world, I am in on the joke and 00:19:31.740 --> 00:19:35.000 I am untouchable. She completely defanged the 00:19:35.000 --> 00:19:37.240 criticism by owning it. Well, what do you think 00:19:37.240 --> 00:19:39.599 the long term effect was? Do you think the movie 00:19:39.599 --> 00:19:41.859 hurt her or did it actually help her? Oh, it 00:19:41.859 --> 00:19:43.940 helped her immensely. Without a doubt. Before 00:19:43.940 --> 00:19:46.440 the movie, she was a very powerful fashion figure. 00:19:46.819 --> 00:19:48.720 After the movie, she was a global celebrity. 00:19:48.819 --> 00:19:51.059 It made her a household name in places that don't 00:19:51.059 --> 00:19:53.759 buy Vogue. It cemented her reputation as a singer. 00:19:53.799 --> 00:19:56.279 incredibly powerful, formidable figure. And in 00:19:56.279 --> 00:19:58.579 corporate America, being feared is often a form 00:19:58.579 --> 00:20:01.059 of currency. But let's look at the reality behind 00:20:01.059 --> 00:20:04.039 that myth. Because the movie shows the tyrant, 00:20:04.140 --> 00:20:06.900 but the biographical sources show something else. 00:20:07.559 --> 00:20:12.500 The machine. Her daily routine is fascinatingly 00:20:12.500 --> 00:20:14.960 rigid. It's an athlete's routine. It's all about 00:20:14.960 --> 00:20:17.819 discipline. She wakes up at 5 .30 a .m. every 00:20:17.819 --> 00:20:21.029 single day. She plays tennis. And she plays competitively. 00:20:21.049 --> 00:20:22.990 This isn't a leisurely hit around with a friend. 00:20:23.089 --> 00:20:25.710 She has a coach. She wants to win. So she starts 00:20:25.710 --> 00:20:27.769 the day with a victory. Yes. And then she arrives 00:20:27.769 --> 00:20:31.710 at the office at 730 a .m. sharp every day. And 00:20:31.710 --> 00:20:34.650 then there's the famous French exit at parties. 00:20:34.750 --> 00:20:36.730 I think this is her secret weapon. This is my 00:20:36.730 --> 00:20:39.190 favorite efficiency hack of all time. He goes 00:20:39.190 --> 00:20:41.430 to the galas, the benefits, the parties she needs 00:20:41.430 --> 00:20:43.670 to be at. She shakes the right hand. She is seen 00:20:43.670 --> 00:20:46.109 by the photographers. And then 20 minutes later, 00:20:46.250 --> 00:20:49.349 gone. She treats socializing as a task on a to 00:20:49.349 --> 00:20:51.609 -do list. Did I make an appearance? Check. I'm 00:20:51.609 --> 00:20:53.730 going home. She's in bed by 10, 1 p .m. every 00:20:53.730 --> 00:20:55.910 night. She understands that her energy and her 00:20:55.910 --> 00:20:58.329 attention are finite resources. She does not 00:20:58.329 --> 00:21:01.190 waste them on small talk. And the diet. There 00:21:01.190 --> 00:21:02.890 are all these stories about her high -protein 00:21:02.890 --> 00:21:06.490 lunch. A steak or a hamburger. No bun. Delivered 00:21:06.490 --> 00:21:09.440 to her desk. Again, efficiency. No time wasted 00:21:09.440 --> 00:21:11.420 deciding what to eat or going out for lunch. 00:21:11.559 --> 00:21:13.819 It's fuel to keep the machine running. And the 00:21:13.819 --> 00:21:15.759 sunglasses. We have to decode the sunglasses. 00:21:16.140 --> 00:21:18.359 They became part of her skeleton. They are the 00:21:18.359 --> 00:21:20.920 ultimate power accessory. She has admitted they 00:21:20.920 --> 00:21:24.059 are armor. And think about her job. She sits 00:21:24.059 --> 00:21:27.160 front row at dozens of fashion shows every season 00:21:27.160 --> 00:21:30.140 for hours on end. If she yawns, if she looks 00:21:30.140 --> 00:21:32.140 bored, if she squints at a dress she doesn't 00:21:32.140 --> 00:21:35.089 like. That reaction could be photographed and 00:21:35.089 --> 00:21:37.750 destroy a young designer's stock price. So the 00:21:37.750 --> 00:21:40.309 sunglasses hide the verdict. They keep the power 00:21:40.309 --> 00:21:42.309 with her. Exactly. It allows her to keep her 00:21:42.309 --> 00:21:45.029 reactions completely private. But there's a great 00:21:45.029 --> 00:21:47.690 little detail in the dossier that I love. They 00:21:47.690 --> 00:21:50.390 are corrective lenses. Wait, really? They're 00:21:50.390 --> 00:21:52.950 not just for show. No. She actually has bad eyesight. 00:21:53.569 --> 00:21:55.970 A colleague once tried them on as a joke and 00:21:55.970 --> 00:21:57.509 said they got dizzy because the prescription 00:21:57.509 --> 00:21:59.430 was so strong. So while everyone thinks she's 00:21:59.430 --> 00:22:02.109 being this cool, intimidating figure, she's also 00:22:02.109 --> 00:22:04.069 just trying to see the runway. It's practical 00:22:04.069 --> 00:22:06.630 and intimidating. The perfect Wintour combination. 00:22:07.049 --> 00:22:09.690 And her leadership style follows that exact same 00:22:09.690 --> 00:22:12.089 pattern. It's decisive. That's where the phrase, 00:22:12.230 --> 00:22:15.049 the Wintour of our discontent comes from. She 00:22:15.049 --> 00:22:17.490 doesn't waffle. You present an idea. She says 00:22:17.490 --> 00:22:20.049 yes or no immediately. There's a bit of a conflict 00:22:20.049 --> 00:22:22.250 in the sources about how much she actually reads. 00:22:22.670 --> 00:22:25.109 Some former staff say she reads every single 00:22:25.109 --> 00:22:27.690 caption in the magazine. Others say she pretty 00:22:27.690 --> 00:22:30.029 much ignores the arts coverage and only looks 00:22:30.029 --> 00:22:32.230 at the pictures. And I think both can be true. 00:22:32.799 --> 00:22:35.440 It suggests she knows her role perfectly. She 00:22:35.440 --> 00:22:38.059 isn't a words editor. She is a visual editor. 00:22:38.319 --> 00:22:40.880 She knows the image is what sells the dream on 00:22:40.880 --> 00:22:43.660 the newsstand. She hired great editors to handle 00:22:43.660 --> 00:22:45.900 the text, but the visual narrative, that was 00:22:45.900 --> 00:22:49.059 100 % Anna. She approved every Polaroid before 00:22:49.059 --> 00:22:51.420 a shoot even began. So she controls the magazine 00:22:51.420 --> 00:22:54.240 with an iron fist. But somewhere in the 90s and 00:22:54.240 --> 00:22:57.180 2000s, her influence expands. She becomes something 00:22:57.180 --> 00:22:59.779 bigger. She becomes a kingmaker for the entire 00:22:59.779 --> 00:23:02.000 industry. This is where we see her transition 00:23:02.000 --> 00:23:05.319 from journalist to business tycoon. And the Met 00:23:05.319 --> 00:23:07.799 Gala is the prime example of this. Before Anna, 00:23:07.940 --> 00:23:11.200 the Met Gala was, what, a local charity dinner 00:23:11.200 --> 00:23:13.500 for society ladies on the Upper East Side? It 00:23:13.500 --> 00:23:16.099 was a fundraiser. It was polite. It was small. 00:23:16.779 --> 00:23:19.619 Anna takes it over in the 1990s and turns it 00:23:19.619 --> 00:23:22.680 into the Super Bowl of Fashion, the Oscars of 00:23:22.680 --> 00:23:25.920 the East Coast. And her big innovation was integrating 00:23:25.920 --> 00:23:28.990 Hollywood. She realized that fashion designers 00:23:28.990 --> 00:23:31.430 alone couldn't carry the publicity. They weren't 00:23:31.430 --> 00:23:33.670 famous enough. So she brought in the actors, 00:23:33.789 --> 00:23:36.390 the musicians, the athletes. She turned it into 00:23:36.390 --> 00:23:39.230 a global media spectacle. She raised over $50 00:23:39.230 --> 00:23:41.990 million for the Costume Institute. They literally 00:23:41.990 --> 00:23:44.269 renamed that part of the museum the Anna Wintour 00:23:44.269 --> 00:23:47.130 Costume Center in 2014. I mean, that is legacy 00:23:47.130 --> 00:23:49.609 right there. But the Met Gala was also a tool. 00:23:49.670 --> 00:23:52.109 It was a way to exert power. If you were invited 00:23:52.109 --> 00:23:54.230 by Anna, you mattered. If you weren't, you didn't 00:23:54.230 --> 00:23:56.789 exist. She controlled the guest list personally. 00:23:57.009 --> 00:23:59.529 She even controlled the seating chart. And she 00:23:59.529 --> 00:24:02.490 used that incredible power to make careers. The 00:24:02.490 --> 00:24:04.970 famous Vogue bump. It's a real economic phenomenon. 00:24:05.329 --> 00:24:07.670 If Anna Wintour liked a young designer, she didn't 00:24:07.670 --> 00:24:09.750 just feature them in a six -page spread. She 00:24:09.750 --> 00:24:12.750 would call the CEO of LVMH or Caring and say, 00:24:12.869 --> 00:24:15.349 you need to hire this person. She anointed John 00:24:15.349 --> 00:24:19.200 Galliano at Dior. That was her. She saved Marc 00:24:19.200 --> 00:24:21.500 Jacobs' career. There's a famous story where 00:24:21.500 --> 00:24:24.180 Marc Jacobs was broke. Completely broke. He didn't 00:24:24.180 --> 00:24:26.619 have a venue for a show. Anna personally called 00:24:26.619 --> 00:24:28.559 Donald Trump, this was back when he was just 00:24:28.559 --> 00:24:31.000 a New York real estate guy, and convinced him 00:24:31.000 --> 00:24:33.480 to lend Jacobs a ballroom at the Plaza Hotel 00:24:33.480 --> 00:24:36.720 for free. She was brokering deals like a Hollywood 00:24:36.720 --> 00:24:39.599 agent. She was. She convinced Brooks Brothers, 00:24:39.799 --> 00:24:42.140 the most traditional American brand, to hire 00:24:42.140 --> 00:24:45.440 Tom Brown, who was a radical at the time. She 00:24:45.440 --> 00:24:47.460 wasn't just reporting on the industry. She was 00:24:47.460 --> 00:24:49.880 staffing it. She was basically a venture capitalist. 00:24:50.000 --> 00:24:51.960 But instead of investing money, she invested 00:24:51.960 --> 00:24:54.460 her influence. But it wasn't all just a smooth 00:24:54.460 --> 00:24:57.279 upward trajectory. She hit some massive walls. 00:24:57.400 --> 00:25:00.039 The 2008 recession, for example. That was a very 00:25:00.039 --> 00:25:02.059 dangerous moment for her and for the Vogue brand. 00:25:02.200 --> 00:25:04.559 The global economy collapsed. People were losing 00:25:04.559 --> 00:25:08.019 their homes, their jobs. Vogue. Well, Vogue kept 00:25:08.019 --> 00:25:10.700 publishing stories about my beautiful villa in 00:25:10.700 --> 00:25:14.940 Tuscany or the best facials for $500. Read the 00:25:14.940 --> 00:25:17.799 room, Anna. It was incredibly tone deaf. She 00:25:17.799 --> 00:25:19.619 was criticized heavily for being out of touch. 00:25:19.819 --> 00:25:22.220 People were calling her Marie Antoinette in sunglasses. 00:25:22.460 --> 00:25:25.539 But watch the pivot. She didn't apologize. She 00:25:25.539 --> 00:25:28.779 diversified. She launched Teen Vogue. Which, 00:25:28.900 --> 00:25:31.799 to be fair, under later editors became this incredible 00:25:31.799 --> 00:25:34.779 politically aware publication. Absolutely. She 00:25:34.779 --> 00:25:37.599 launched Men's Vogue, which had record ad pages 00:25:37.599 --> 00:25:40.359 at its launch, though it later folded. She launched 00:25:40.359 --> 00:25:43.250 Vogue Living. She pushed the brand into every 00:25:43.250 --> 00:25:45.289 corner of the market. She was trying to make 00:25:45.289 --> 00:25:48.509 Vogue an unassailable lifestyle, not just a magazine 00:25:48.509 --> 00:25:50.369 you buy once a month. And then came the biggest 00:25:50.369 --> 00:25:53.670 pivot of all, the 2020s, the beginning of the 00:25:53.670 --> 00:25:55.910 end of the reign. The year 2020 was the year 00:25:55.910 --> 00:25:58.009 it almost ended for her. The murder of George 00:25:58.009 --> 00:26:00.849 Floyd triggered this massive global examination 00:26:00.849 --> 00:26:03.970 of systemic racism in every industry, especially 00:26:03.970 --> 00:26:07.509 media. And Vogue was not spared. An investigation 00:26:07.509 --> 00:26:09.430 by the New York Times came out that indicated 00:26:09.430 --> 00:26:12.619 that Black women, black writers, black photographers 00:26:12.619 --> 00:26:15.559 had been systematically sidelined at Vogue for 00:26:15.559 --> 00:26:17.859 years. And this wasn't just external noise from 00:26:17.859 --> 00:26:19.819 critics. This was coming from inside the building. 00:26:19.960 --> 00:26:23.539 And then the ultimate betrayal. Andre Leon Talley. 00:26:23.740 --> 00:26:27.559 Her right -hand man for decades. The larger -than 00:26:27.559 --> 00:26:29.500 -life editor who sat next to her in the front 00:26:29.500 --> 00:26:32.839 row at every single show. He published his memoir, 00:26:33.019 --> 00:26:36.259 The Chiffon Trenches, in 2020. And he absolutely 00:26:36.259 --> 00:26:39.440 dismantled her public image. He painted her as 00:26:39.440 --> 00:26:43.259 cold. dismissive and cruel. He basically said 00:26:43.259 --> 00:26:46.599 that once he was no longer useful or cool in 00:26:46.599 --> 00:26:48.940 her eyes, she cut him off completely. That must 00:26:48.940 --> 00:26:51.119 have hurt personally, but it also really damaged 00:26:51.119 --> 00:26:53.799 the brand. It did. And for the first time, Wintour 00:26:53.799 --> 00:26:56.500 issued a rare apology to the staff. She sent 00:26:56.500 --> 00:26:58.700 a memo admitting that Vogue had been complicit 00:26:58.700 --> 00:27:00.960 in racism and had not done enough to elevate 00:27:00.960 --> 00:27:02.880 black voices. And many people in the industry 00:27:02.880 --> 00:27:05.119 thought, this is it. She's done. She can't survive 00:27:05.119 --> 00:27:07.160 this. The rumors were flying. Everyone thought 00:27:07.160 --> 00:27:09.380 she would resign in the summer of 2020, but she 00:27:09.380 --> 00:27:12.680 didn't. How did she survive? Her peers, people 00:27:12.680 --> 00:27:15.079 like Tina Brown at The New Yorker, Graydon Carter 00:27:15.079 --> 00:27:18.160 at Vanity Fair, they all left years ago seeing 00:27:18.160 --> 00:27:20.660 the writing on the wall for print media. How 00:27:20.660 --> 00:27:23.599 did Anna hold on for so long? She adapted. This 00:27:23.599 --> 00:27:25.900 is the key learner insight of her later career. 00:27:26.240 --> 00:27:28.759 She realized the job title editor -in -chief 00:27:28.759 --> 00:27:31.799 was becoming obsolete. So she made herself something 00:27:31.799 --> 00:27:35.759 bigger. She became the global chief content officer. 00:27:36.160 --> 00:27:37.519 What's the real difference there? Is it more 00:27:37.519 --> 00:27:40.059 than just a title change? It's everything. An 00:27:40.059 --> 00:27:42.519 editor worries about the next issue of one magazine. 00:27:42.880 --> 00:27:45.319 A chief content officer worries about the brand 00:27:45.319 --> 00:27:48.440 across all platforms globally. She consolidated 00:27:48.440 --> 00:27:51.180 power. She took control of all the international 00:27:51.180 --> 00:27:54.339 Vogue editions. She made herself structurally 00:27:54.339 --> 00:27:56.759 essential to the corporate mothership of Condé 00:27:56.759 --> 00:27:59.019 Nast. She wasn't just making magazines anymore. 00:27:59.079 --> 00:28:01.700 She was managing a global digital ecosystem. 00:28:01.880 --> 00:28:04.019 She was also politically insulated. She became 00:28:04.019 --> 00:28:06.119 a massive fundraiser for the Democratic Party. 00:28:06.220 --> 00:28:09.269 A major bundler for Obama. Hillary Clinton, for 00:28:09.269 --> 00:28:11.869 Joe Biden. There were persistent rumors she was 00:28:11.869 --> 00:28:14.130 being considered for ambassador to the UK if 00:28:14.130 --> 00:28:16.789 Clinton had won. She had very powerful friends, 00:28:16.869 --> 00:28:19.210 not just in fashion, but in Washington, D .C. 00:28:19.349 --> 00:28:23.329 Which brings us to last year, 2025, the exit 00:28:23.329 --> 00:28:27.150 strategy. It felt very planned. It was masterfully 00:28:27.150 --> 00:28:30.690 choreographed. A perfect endgame. Step one, January 00:28:30.690 --> 00:28:34.210 2025. President Biden awards her the Presidential 00:28:34.210 --> 00:28:36.650 Medal of Freedom. The highest civilian honor 00:28:36.650 --> 00:28:38.450 in the United States. And that award did something 00:28:38.450 --> 00:28:40.670 important. It legitimized her entire career. 00:28:40.849 --> 00:28:43.430 It sent a message. This woman didn't just pick 00:28:43.430 --> 00:28:46.450 clothes. She shaped American culture. It was 00:28:46.450 --> 00:28:48.730 the ultimate stamp of establishment approval. 00:28:49.049 --> 00:28:53.049 And then six months later, June 2025, she steps 00:28:53.049 --> 00:28:55.769 down as editor -in -chief. She hands the reins 00:28:55.769 --> 00:28:58.710 to Chloe Mao, who was the editor of Vogue .com, 00:28:58.809 --> 00:29:01.630 a very deliberate choice. a digital native to 00:29:01.630 --> 00:29:03.990 lead the brand into the future. But notice the 00:29:03.990 --> 00:29:06.849 nuance. Anna didn't retire. She's still hovering. 00:29:06.970 --> 00:29:09.430 She remains global chief content officer for 00:29:09.430 --> 00:29:11.930 Condé Nast internationally. She gave up the day 00:29:11.930 --> 00:29:14.029 -to -day grind of running U .S. Vogue, but she 00:29:14.029 --> 00:29:16.210 kept the global strategy role. She's still on 00:29:16.210 --> 00:29:18.029 the board. She's still pulling strings. She just 00:29:18.029 --> 00:29:20.329 can't let go completely. I don't think she knows 00:29:20.329 --> 00:29:22.670 how to not work. There's a famous line about 00:29:22.670 --> 00:29:25.529 sharks that if they stop moving, they die. I 00:29:25.529 --> 00:29:27.650 think Anna Wintour is a bit like that. So let's 00:29:27.650 --> 00:29:30.759 zoom out. When we look back at this entire 37 00:29:30.759 --> 00:29:33.759 year reign, what is the legacy? What does it 00:29:33.759 --> 00:29:36.190 all mean? At the end of the day, Anna Wintour 00:29:36.190 --> 00:29:38.430 wasn't just a fashion editor. She was the CEO 00:29:38.430 --> 00:29:41.390 of Taste. She professionalized an entire industry. 00:29:41.789 --> 00:29:44.349 She took a world that was erratic and whimsical 00:29:44.349 --> 00:29:47.369 and, frankly, a bit of a mess, and she imposed 00:29:47.369 --> 00:29:50.230 a corporate structure on it. She merged Hollywood 00:29:50.230 --> 00:29:52.369 and fashion in a way that is now the absolute 00:29:52.369 --> 00:29:54.730 standard. You can't imagine one without the other 00:29:54.730 --> 00:29:57.210 now. She did. She made the T -shirt and jeans 00:29:57.210 --> 00:30:00.569 on a magazine cover fashion. She made the Devil 00:30:00.569 --> 00:30:05.079 Wears Prada villain an icon. global holiday. 00:30:05.220 --> 00:30:07.240 She was the last of the great gatekeepers, the 00:30:07.240 --> 00:30:09.559 last monarch. I think that's right. And that 00:30:09.559 --> 00:30:11.980 leads me to the big question for our listeners 00:30:11.980 --> 00:30:15.960 today. We are now in 2026. The algorithm feeds 00:30:15.960 --> 00:30:18.440 us what it thinks we want to see. Influence is 00:30:18.440 --> 00:30:20.480 fragmented into a million different TikToks and 00:30:20.480 --> 00:30:23.099 sub stacks. With Wintour stepping back from that 00:30:23.099 --> 00:30:26.119 central role, will there ever be a single gatekeeper 00:30:26.119 --> 00:30:29.240 of culture this powerful again? It doesn't feel 00:30:29.240 --> 00:30:32.099 possible, does it? I don't think so. The internet 00:30:32.099 --> 00:30:35.339 has democratized taste. for better or for worse. 00:30:35.599 --> 00:30:38.859 No single person can say, hemlines are going 00:30:38.859 --> 00:30:41.619 up this season and have the entire world obey. 00:30:41.859 --> 00:30:44.940 That kind of centralized power died with her 00:30:44.940 --> 00:30:48.619 reign. We are in the era of the microtrend, not 00:30:48.619 --> 00:30:51.160 the monolith. It really is the end of the monarchy. 00:30:51.819 --> 00:30:55.220 The queen is, if not dead, at least in semi -retirement. 00:30:55.299 --> 00:30:57.910 Long live the algorithm. It seems that way. So 00:30:57.910 --> 00:30:59.950 next time you throw on a blazer with your jeans 00:30:59.950 --> 00:31:02.349 or you find yourself judging a celebrity's outfit 00:31:02.349 --> 00:31:04.670 at the Met Gala, just remember, you are living 00:31:04.670 --> 00:31:07.029 in the world that Anna Wintour built, even if 00:31:07.029 --> 00:31:08.730 she's no longer sitting in the front row. Whether 00:31:08.730 --> 00:31:10.789 you like it or not. That's it for this deep dive. 00:31:10.890 --> 00:31:11.549 Thanks for listening.