Newsletter 43: Why Is Kellyanne Conway Following Me on Twitter?

Will Leitch
7 min readOct 26, 2018

I’ve decided to start putting some of the best newsletter essays here on Medium, so more people can read them. You’re still better off just subscribing. This one is from February 2017, when I tried to figure out why Kellyanne Conway was following me on Twitter. It has been nearly 19 months later, and she is still following me, and I still don’t know why.

Earlier this week, actor Seth Rogen — I’m generally a fan, with exceptions — realized that Donald Trump Jr., the son of the human-type-substance that currently occupies the office of President of the United States, was following him on Twitter. Because you can send Direct Messages to people who follow you on Twitter, Rogen realized, “Hey: I can just tell this dude what I think right now.” So he did, sending him a series of (presumably unanswered) requests for his father to, you know, stop terrifying us all that he’s going to blow up the planet and go back to hosting a television show, a job he’s better suited for and one he seems to enjoy a lot more anyway.

Some people didn’t like Rogen’s gimmick — Ashley Feinberg, who might be my favorite political writer right now, got in a Twitter fight with Rogen over it — but I enjoyed it, for three primary reasons.

1. There’s something cathartic about it. That sense of helplessness we all have, that oh shit he’s going to burn everything down and we might not be able to do anything about it, it’s a real thing. It’s frustrating and exhausting and it just weighs you down, all hours of the day. So I understand Rogen’s instinct here. Wait … the son of the guy doing all of this … I can just send him a message? I don’t think Rogen believes he will make a difference, and there’s a performative aspect to this that probably ruins any good Rogen could actually do anyway. But I get the idea.

2. He’s handling it the right way. He’s being funny and charming and lighthearted and polite about it: Hey, man, could you be a pal and maybe stop us from all dying? The stunt works a lot better if he’s not going all Sarandon on him.

3. I’ve thought about doing the same thing every day since Election Day.

On July 1, 2016, then Republican Presidential candidate Donald Trump added a woman named Kellyanne Conway to his staff. The Washington Post did a short item about her hiring, but it wasn’t considered a big deal: Trump’s statement — which is to say, “words that he obviously never said and were obviously written by someone else” — says, “Kellyanne is a tremendous asset to our rapidly-expanding campaign team. She is a data and messaging expert and terrific on TV. It is great to have her on board.” No one thought too much about it. But at the end of August, with his campaign (once again) devolving into chaos, Trump announced that he was bringing Stephen Bannon on as campaign CEO and promoting Conway to campaign manager. This was seen as a move of desperation, which it was, but, uh, it turned out he won the election so now these two random people hopping on the sinking ship are among the most powerful humans on the planet.

I’d heard about Bannon, but I didn’t know Conway, so I looked her up. And there it was: She was following me on Twitter.

Now, Conway is not following tens of thousands of people on Twitter just to boost up her follower count: She’s no Taye Diggs. She followed roughly 520 or so people back then — she follows 626 now — which is half of the number of people I follow. I follow people for lots of reasons, because I know them, because I admire their work, because they cover a subject I particularly care about, because they owe me money and I must track their movements at all times, you know, lots of reasons. But there is a reason for every one of them. I made the decision to follow them. I’ve unfollowed plenty of people in my time too; of the 1,285 people I follow, I made the decision to continue to follow them.

In August 2016, I was writing regularly for Bloomberg about politics, so I figured that was it. She had seen that I did a podcast with John Heilemann, and just figured I was another political media person to keep an eye on. But then I researched further and realized that not only was she not following John, she wasn’t really following many people at Bloomberg at all. If she wasn’t following senior people like John there, but she was following me, it couldn’t be that. I also thought there might be, like, a secret journalist destined-for-the-gulag list that I’d stumbled my way on, and then I realized that if there were one — and there probably is! — it probably wouldn’t so obvious as “people who Kellyanne Conway follows on Twitter.”

Did I know her? Had I met her? I did not think that I had, but I went ahead and checked my email archive — which has essentially every email I’ve sent since 2001, though it’s Yahoo, which means now Russia has access to every email I’ve ever sent — and she never came up. So that wasn’t it.

Maybe she’s a big sports fan? She’s an Eagles fan — Deadspin dug up some old bad prediction Tweets she made about Chip Kelly — and she actually linked to something Drew Magary wrote back in November. But when I went to look and see whom she was all following on Twitter, she wasn’t following Drew, or Deadspin’s account, or really many sports accounts at all.

In fact, when I dug into it … it appeared she had been following me for quite some time. Here are people whom Kellyanne Conway began following after she started following me:

  • Steve Bannon
  • Breitbart News
  • Ben Carson
  • Bill Clinton
  • Hillary Clinton
  • Stephen Colbert
  • Ted Cruz (whom she initially worked for)
  • The Department of State
  • General Michael T. Flynn
  • Matt Lauer
  • Corey Lewandowski
  • Rush Limbaugh
  • Barack Obama
  • Omarosa
  • Mike Pence
  • Sean Spicer
  • Jill Stein
  • Roger Stone
  • Melania Trump and all of the Trump children
  • Wikileaks

Actually, when you look at it, I think I was followed right around the exact same time as Ted Cruz and Nick Foles.

Now, another aspect to this mystery is, well, I don’t particularly consider myself much of a must-follow on Twitter. I really only Tweet out my pieces and links to this newsletter anymore, along with occasional observations on how freaking terrifying it is living under a President Trump. I’m not sure I provide a ton of value added on Twitter. It’s not the right platform for me, for reasons we’ve discussed in past newsletters. Even if she had a spontaneous “hey, I’ll follow this guy because I liked this particular piece he wrote” four years ago, surely, she has seen enough to realize it’s not worth continuing since then.

So I don’t know. I don’t know why Kellyanne Conway is following me on Twitter. But you know what the worst part about this? Is that for months, and months and months and months, after all the horrors of the Trump Black Hole we’ve all been plunged into became even more clear than they already were, I always sort of, quietly, to myself, thought, Kellyanne Conway must be so embarrassed by all this. She must be screaming to get away. What evidence did I have to think that Conway was any different than all those goons surrounding that guy? I had that actually-sort-of-charming standup routine from 1998 — c’mon, man, comedy is hard — and, well, the fact that she was following me on Twitter. I legitimately had the thought, for an extended period of time, that Kellyanne Conway must not be that bad, because jeez, she follows me! She must secretly get that this is all crazy, right?

The clearest proof yet that Twitter is destroying us all, and also that I am an idiot.

So now, here we are. I wasn’t even going to write about this, but the way this administration is going, she may be gone in a week. (Or she may be put in charge of the nuclear arsenal. I mean, who knows with these guys, right?) She may see this and unfollow me, or, more likely, see it, think “wait, when did I follow this moron?” and justly unfollow right then and there. Or maybe she’ll never see it at all. But this has been driving me crazy for months now. And if I’m thinking about something for months that has no logical place for publication, well, that’s what this newsletter is for.

So if you’re reading this, Ms. Conway, know that I do actually have some respect for you. To have risen as far as you have in such a male-driven field shows ambition and intelligence and resilience. But please stop lying on television, and, if you could, if you don’t mind, please tell your boss not to blow up the planet. I have kids like you do, and I want the world to still be there for them. Thank you.

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Will Leitch

Author of six books, including “How Lucky” and "The Time Has Come." NYMag/MLB.. Founder, Deadspin. https://williamfleitch.substack.com