While hosting MSNBC's "The Last Word,"  Lawrence O’Donnell has never held back about the danger Donald Trump poses to our democracy, or how he feels about him. Several times on his broadcast, O'Donnell has referred to Trump as the stupidest person to ever run for president.

But it’s another matter entirely to scrutinize one’s industry in full view of the TV audience, which O’Donnell has done regularly. For those wondering why most campaign reporting doesn't yield much light or information, O’Donnell is a sanity check. It's because both candidates have been covered by some terrific reporters, he tells his audience, and a lot of terrible ones too.

“This is my least favorite subject,” O’Donnell told me on Friday, referring to his criticisms of his peers in journalism. “When I do it, I'm trying not to be holier than thou in every way that I can. And I fail at that a fair amount.”

“I just don't want to pretend that I'm, you know, smarter than other people about how to handle this,” he said. “I just kind of have publicly embraced and acknowledged the difficulty of doing it.”

He added, “And I try to always say there are brilliant reporters out there.” 

Election night is when the coverage mission is clearer and gets easier. On Tuesday, O’Donnell will be contributing to a team led by Rachel Maddow that includes Nicolle Wallace, Ari Melber, Joy Reid, Alex Wagner, Stephanie Ruhle, Chris Hayes, and Jen Psaki, with Steve Kornacki piloting the channel’s iconic “big board” as the vote counts roll in.

Nevertheless, in the months leading up to the election he’s joined us in watching establishment media outlets make the same mistakes as they did in 2016 and 2020, including trafficking in false equivalencies, sane-washing Trump, and failing to construct useful questions for candidates and their surrogates. We can all see the stumbles. O’Donnell is simply one of the few bothering to call them out. 

“It's a field that I would say lacks imagination and lacks real perception about human beings, about characters,” he said. “You know, I know many dramatists who understand Donald Trump in this moment far better than people working at newspapers and news organizations do.” 

O'Donnell's career spans entertainment, journalism and politics. Before working in cable news, he was the senior advisor to Sen. Daniel Patrick Moynihan and served as the chief of staff on two Senate committees. He joined MSNBC in 1996 as a political analyst, and was a writer and executive producer for “The West Wing," which won the 2001 Emmy for best drama series. O'Donnell went on to create the TV drama “Mister Sterling” as well as playing a recurring role in HBO's “Big Love.”

He has hosted “The Last Word” since 2010 and has had a role in MSNBC's election coverage since 2000. In that time, and certainly since Trump came on the scene, he’s drawn some conclusions about what’s ailing TV news. In the final days of an election season that has felt interminable, he shared a number of them with Salon in a wide-ranging interview.

The following interview transcript has been edited for length and clarity.

What do you feel are the main reasons that the media hasn't changed the quality and insightfulness of its political coverage since 2016?

So, when I do criticize the coverage on my show, you are seeing something on the order of 1% of my dissatisfaction with the coverage . . . it's just in the most egregious moments that I just feel compelled to say something. What I don't like about it is the notion that I have somehow figured out how to cover Donald Trump. No one has. That's the problem. And the only distinction that exists within the political media is those who know they haven't figured out how to cover Donald Trump and those who don't know. Unfortunately, the profession is dominated by people who think they've figured it out. And that's really the problem.

It's a challenge unlike anything this field has ever seen in its history. It's worthy of complete, “stop everything meetings” in news organizations nine years ago to say, “Wait a minute, how do we cover this? This is just outright lying. We've never actually had to cover this kind of lying before. Do we have tools for this?” And those meetings never happened.

. . . Look, I don't think anything illustrates the lag time, just how far behind the established news media has been in what they're dealing with than this, and it's personal. The first time I called Donald Trump a liar and said the word “lie” about what he was saying was in 2011, the very first time he opened his mouth about Barack Obama's birth certificate.

The first time The New York Times used the word lie in relation to Donald Trump was five years later in September 2016, when he was already the Republican nominee for president, and it appeared on the front page of The New York Times in the lower left corner with the word “lie” in the headline. And the lie they were referring to five years later was Donald Trump's lie about Barack Obama's birth certificate.

And the idea of lying was discussed in many newsrooms and many media columns: Should it be called a lie? Defining a lie. That's very frustrating.

Yeah, and because I grew up in reality, and I didn't grow up in a news organization like that, I knew what a lie was, and I also knew legally, yes, I can call it a lie, because it is a lie. Other people were encumbered by concerns at the time, possibly about, you know, is that libelous? Can you get in legal trouble for saying that word? And I understood all that stuff, and it took a full understanding of all that stuff to do that. And a real understanding of guys like Trump. I mean, I grew up with idiots like that, you know.

And I think unfortunately, and I say unfortunately for the current purposes, more than 90% of the news media was never around idiots like Trump. They didn't grow up in those kinds of streets, in those kinds of urban sectors where those guys are all over the place. You know that idiot at the bar, that stupid racist. If you didn't grow up around a lot of stupid racists, it's going to take you a long time to figure out what Trump is.

I just want to segue into this idea of this being the podcast coverage campaign. It was very educational to watch how Joe Rogan handled Donald Trump because it was not just a matter of not knowing how to deal with him. He was fascinated by him. There's this tenor of conversation that's leaked into the interview that has tainted the quality of coverage, or the ability to cover him.

I realize that when we look at what podcasters are doing versus what mainstream journalists are doing, we should be considering those approaches very differently. But the public does not. Is that frustrating for you to witness?

Well, yeah, and I think your piece about the Trump Rogan interview is so important because, of course, I didn't listen to the three hours. I didn't listen to any of it. The only bits of what I heard are the pieces that were clipped for television. And what your piece shows is how much television fails when it does that. The classroom example of it, especially the bit that they used, you know, where Rogan chuckles about Trump, you know, saying that he won the election. And then it turns out in your reporting, if you extend that conversation long enough, you're going to find that Rogan is not contradicting him.

Nope.

In fact, he's kind of on board with it. There's not a moment in what I read of your reporting of it where Rogan departs from that. It's an incredible challenge trying to deal with that. And TV news is always, by definition, presenting a limited version of whatever we're talking about. And the best recommendation that exists for anyone is to go, check the original sources. .. it's worth bringing your own scholarship to this kind of coverage because we're all limiting it in some ways.

Let’s talk about the contrast between what Bill Whitaker did on “60 Minutes” in interviewing Kamala Harris versus what happened with Brett Baier. On the one hand, my frustration with Bill Whitaker was that he kept going at the same questions that Harris was prepared to answer and pivot from. On the other, you have Baier trying to show he's tough by antagonizing and talking over her.

There's this misinterpretation of what it means to do insightful, tough journalism that has turned interviews into an argument that serves no one. My question to you is whether an unfair assessment of what it means to kind of conduct is not necessarily an antagonistic interview, but something that's probing. I don't see enough in this election cycle, if any, that have served to answer the public's questions.

Political interviewers now are not in the business of illumination. They are in the business of impressing the other people who do political interviews. That's the most important audience to them. They don't care about the two or three million who might see it on TV. They care primarily about other people who do this for a living because those are the people who issue their report cards within the business. The biggest compliment you can get after doing an interview with any politician is that you asked tough questions. And there is this religious belief that the tough question is somehow the important way to get at some kind of truth.

The mindset of every interviewer now in politics is not illumination. It is prosecution. You are judged by how good a prosecutor you were, and you must be a fair prosecutor. Brett Baier was judged to be an unfair prosecutor who cheated the unwritten rules of how you do this. And of course, Brett Baier is a totally partisan Republican who was embarrassed his network did accurate coverage during the last presidential election when they called Arizona, and he wanted them to retract the call. We've seen all the texts of his.

But even if you're not doing it Brett Baier style, the only way you will be judged by your peers to have done a good job was, “How good a prosecutor were you? Not, “How good an illuminator were you?" That is not what they are trying to do, and that's the gap between them and the voter. Because the voter invariably comes back and tells you, yeah, “I wasn't interested in that part. I'd like to know this.” And oh, well, they didn't cover that.

Going back to the original problem of how to interview Trump, there's been so much of this demand that you call out his lies while not providing any meaningful information about policy and relevant facts, and I think that has bled into journalism in such a way that I’m not sure we know how to find our way back. To me, I think that's been the defining issue of campaign coverage. I don't know whether you agree with that, or if you see something else.

No, I do, and I would point out another characteristic of the profession that's a problem, and it goes to this point of every interviewer trying to impress other people in their field. That's the first thing they're trying to do. And I don't mean the Rogan types. I mean the Washington press corps.

That's why they never ask a simple question, because if their question is too simple, that would indicate their minds are too simple.

. . . The one I've proposed that none of them have ever asked Donald Trump is: What is a tariff?

Yes. Thank you.

They have never asked that question. And my feeling is — and I could be wrong, but having studied the way the Trump interview goes — if you ask that question, you're going to actually get at something so much more important than any of these other questions that you might ask, including that Trump doesn't know what a tariff is.

That's a very distinct possibility. And if you just were to stay with it and the ramifications of that question —  because you know, or you're supposed to know, that he's lying about who pays the tariffs. So don't begin with the lie. Don't start there. Start before the lie. Start with, “What is a tariff,” and you'll get to the lie soon enough. But no one will ever ask the question, because that question will sound too simple and it won't sound like something that was workshopped by all the network executives who came up with the question for you, or whoever it was.

And so I think that's one of the big issues that comes out of the fact that interviewers are all trying to impress other interviewers. If you could correct one thing, it would be to get that out of the psyche of the interviewers.

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I'm going to ask this next question which, in the spirit of what you just said, is very simple . . . What do you feel that MSNBC is doing differently in all this?

I'll say one thing that I'm doing differently, and it's the only thing that I know I'm doing differently. And I mean this with the utmost humility because I know how tiny this is.

There came a time — I'm not sure when, sometime in the last year — where I found it so dispiriting to put Donald Trump's lies on the screen that I came up with this idea of saying, "Okay, we're not going to give them our entire screen." We're going to give them half of the screen, and I will occupy the other half of the screen, as a way of saying to the audience, “This is not the same as any other politician speaking clip that we show you. This is a pathological liar. This is a madman, and he's going to be treated differently here, and I'm not going to leave you alone with him. You will not be alone in your living room with him. I won’t do that to you."

And that's it. That's why he gets half the screen. And it's tiny. It's literally next to nothing, but it's me just sitting there trying to think of, "What do we need to do that's different? What does your TV frame need to include for you to say to you, “This is different”?

I come from a world where I care about every single thing in that frame. It's actually the worst way to come to this line of work. I came to it from filmmaking, you know, drama series  . . . there's not a thing in that screen that you do not care about, because it is all part of what's going to happen to that audience and what the audience is going to feel. I may be the only one who cares about every single thing that's on our screen. And, in thinking about that, that's just the little adjustment that I came up with.

I offer it not as a cure for anything. I offer it as an example of one person desperately trying to figure out how to cover this horrible thing that we have to cover, which is this candidate who actively wants to destroy everything that we have all wanted for this country. And what's laughable about it is how tiny a thing that is.

"The Last Word with Lawrence O'Donnell" airs weeknights at 7 p.m. PT/ 10 p.m. ET on MSNBC.