Keith Olbermann really, really hates me

What I do -- and why.

On Friday afternoon, in the immediate wake of the news that Donald Trump had named his campaign manager, Susie Wiles, as his presidential chief of staff, I tweeted (X’ed?) out what I thought was a fun fact: That Wiles is the daughter of former NFL kicker and legendary CBS broadcaster Pat Summerall.

Not exactly a bombshell! But, I thought, interesting enough to mention amid all of the Wiles talk. And it seemed, well, pretty innocuous to me. Love or hate Trump or Wiles, the fact that her dad was very famous is intriguing!

Well, Keith Olbermann disagreed.

This is, um, not the first time Keith has gone after me.

There was this one when I did a TV hit on MSNBC this fall:

And the innumerable times Keith has attacked me — this year alone — on his quite-popular podcast. (Note: I don’t listen to it but people who do always like to send me an email or a direct message to alert me to the fact that Keith has, once again, gone after me. Thanks, or something!)

Which leads me to a question I get all the time: Why does Keith hate you?

I’ve avoided engaging with that question — mostly because I was super busy writing about the election — but I spent a little time thinking about it over the weekend and wanted to share my conclusion because I think it gets to what I do and why I do it.

Start here. Keith has not always hated me! In fact, Keith used to put me on TV — back when he hosted the terrific “Countdown” show on MSNBC.

I have proof! Here’s a transcript of a show I appeared on! In August 2007! (I used to do “Countdown” once every other week or so back then.)

It’s been a long time since those days — and both Keith and I have had winding roads to where we are today.

You know my path — and where it’s led me.

For Keith’s part, he left MSNBC — abruptly, as is his wont — at the start of 2011. He went to Current TV, the short-lived Al Gore-vehicle.

In 2022, he posted a long Twitter thread about how MSNBC had been courting him to return for the better part of a decade. “Won’t happen. Should’ve,” Olbermann concluded.

MSNBC, at the time, denied his account. “There was never any serious consideration of Keith Olbermann returning,” a spokesperson for the network told Variety at the time.

Regardless! Keith has been on his own in the last few years — and appears to be doing very well! His podcast is popular. He has 985,000 followers on X!

Which makes sense, honestly. I have said before and will say here again: Keith is a genius when it comes to talking on TV or podcast or whatever. He is an amazing performer with an incredible memory and the ability to recall almost anything — whether it’s political stats or baseball stats — on command.

His genius for TV is why he has been given SO many chances — in both the politics and sports space. His former employers read like a who’s who of big media companies: ABC, ESPN, CNN, Fox Sports and MSNBC.

But, even back when I was doing TV with Keith — lo those 17 years ago! — he was clearly a liberal. He did some accountability coverage of both parties but he clearly leaned into giving Republicans hell.

It was MSNBC! It worked! Mostly because — see above — Keith is an incredibly talented TV personality.

In the intervening decade and a half, Keith has gotten much MUCH more liberal. Or maybe he was always that way but he just got less inhibited about showing it off.

Either way, it doesn’t matter. Keith isn’t a journalist anymore. He’s an activist. And an advocate. Don’t believe me? Here’s the latest episode of his pod:

Which is totally fine! Like, Keith can do and say whatever he wants!

But I think in Keith’s liberal activism lies the real reason why he doesn’t like me.

(Sidebar: I think if you asked Keith why he loathes me, he would say I am colossally stupid. Or a unwitting accomplice of a fascist regime. You get the idea. Also worth noting: Keith hates LOTS of people. I am not unique in that regard 😂😂😂)

Because, I am not what Keith is. I never have been.

I was trained — with Charlie Cook, Roll Call, the Washington Post and CNN — as a journalist. Which doesn’t mean I don’t have opinions. I do! But my opinions aren’t always predictable. I don’t think everything Donald Trump does or says is inherently terrible because, well, Trump said it or did it. I didn’t buy into all the hype around Kamala Harris when she became the nominee. I didn’t tell you she was definitely going to win — because I didn’t think she would!

Which is a choice I have made. I believe — and have said repeatedly — that Trump represents a radical reimagining of the presidency. And that he has, without question, authoritarian impulses.

And I believe that.

But I also believe that my job isn’t to tell you what you NEED to think. Or SHOULD think. It’s to explain why people think what they think. To offer context. Fact checking. Reality checking. And, above all, to make sure that I am putting objective facts — not just my opinion — behind what I write and say.

NONE of this means I will get it right all the time. I told you all I thought Trump had a slight advantage in the election. Had Harris won, I would have been technically “wrong” (even though I said over and over that it was too close to call).

The point is I am no smarter or dumber because I thought Trump had a narrow edge than I would be if I said Harris had that same edge.

My only goal — throughout my media career but especially nowadays — is to be authentic and transparent. When I get it right, great! When I get it wrong, I want you to be able to see my work and understand how I got there.

The other really important thing about me is that I don’t root for a side. And I don’t have some corporate overlord putting his or her finger on the scale of what I write. Everything in this newsletter — and on my YouTube channel — is what I genuinely believe based on my many years of writing and reporting about politics. Which, again, is no guarantee it’s right! But I can guarantee you it comes from an authentic place.

For Keith, not rooting for a side is anathema. He can’t imagine how ANYONE can do that. And he has special enmity for people like me who he once knew in journalism.

Which is ok! He has every right to his points of view! And I am sure that if he sees this piece, he will attack it — and me! Again, fine! I don’t think I am going to change his mind.

Here’s what I will say: I spend very, very little time paying attention to Keith. I’ve muted him on X. As I said above, I don’t listen to his podcast.

Keith may hate me. I don’t hate him. I’m indifferent to him. That’s the truth.