Samantha Bee Is Asking Her Viewers to Write More Sternly Worded Letters

Like many who professionally straddle the line between comedy and journalism, Samantha Bee’s been quite distracted for the last five years. Even with weekly outlet Full Frontal, she and her team passed over story after story as the Trump presidency and then the pandemic hijacked their collective bandwidth.

But Bee checked a big one off of her long to-do list on Wednesday night, releasing a piece about Reality Winner — the woman, with a very unique name, who went to prison three years ago after leaking NSA documents that proved Russia’s tried to interfere with the 2016 election. The information that the Air Force veteran and former intelligence specialist shared has been since used by states to secure voting practices, yet Winner remains incarcerated. Bee hopes this new segment will rectify that. “Commuting Reality Winner’s sentence is a gesture that can be done with the stroke of a pen,” says Bee. “It’s not a super challenging item on the docket.”

Speaking over the phone, while navigating Manhattan traffic, Bee discussed her campaign for the Biden administration to free Winner, the liberation of a post-Trump news cycle and the improbable persistence of women’s hosiery.

A clip of the full segment follows our conversation.

Going into this episode, all I remembered of Reality’s whole ordeal was her name.

It’s funny, because her name is so interesting and it’s so unique. People forgot so quickly what actually happened, but everyone knows her name. Everyone just thinks that she is the woman who won a reality show competition, even though we were all talking about this story briefly four years ago.

Edward Snowden became a fixture in the news for doing something very similar. Why do you think this story didn’t get more attention?

I actually can’t believe that her story hasn’t captivated people more. It’s really interesting. It has really changed America. The information that she revealed, many states have been using it ever since to secure their election system. That’s huge. I think part of what happened is that Reality Winner just didn’t have her own hive. So, we’re trying to be that hive.

The story faded too quickly, so I’m really excited to bring it back. We need just to remind people of the debt that we owe Reality Winner, because we actually really do. There’s a commutation petition in place, and I really hope that the Biden administration honors that. She really made a difference. She’s a whistleblower, she’s not a spy.

In terms of timing, what made you do the piece now?

I’s sad to say this, but I think that the news cycle for the past four years was just such a rollercoaster ride. Like many other shows, we were just treading water. Stories were coming at us fast and furious. We had a plan to talk about Reality Winner. Unfortunately, it fell by the wayside. And sometimes you just lose the thread of telling those stories. I regret that we didn’t do this story a lot earlier, because I think that Reality has had a really hard time in prison, and its been really difficult during COVID, and I wish that we had put attention on this earlier than we were doing. However, I’m glad that we’re doing it now.

Forgive my ignorance on logistics, but you’re not allowed to interview Reality because she’s incarcerated?

That’s correct. We were not able to interview Reality herself, so we spoke her older sister, Brittany, and her attorney, who is working on the commutation petition. They both explain the story with such entertaining clarity, which is just the perfect storm. That almost never happens.

Did you consider reaching out to the reporter who leaked her identity to the NSA?

I don’t think so, because it’s not really his story that we’re telling. It 100% was, the document was mishandled, and really demonstrated really poor judgment. Pretty much whistleblower 101. Do not share the original document with identifying markers on it.

Reality’s critics really hammered this narrative that she hated America, because she’d written in a diary that she wanted to burn down the White House. That seems like something that a lot of people joked about during the last administration. What kind of impression did you get about her motivations?

We all did. We literally make jokes like that at every day on the show. It’s how you blow off steam. Part of what prompted her to leak the information was her immense distress at the state of the country with Donald Trump as president. People were talking about Russian interference in our election system. That was the conversation that everyone was having, and she was distraught. We’ve all made jokes about how America is awful and continue to do so. It doesn’t mean we don’t love it here. She absolutely loved the country. Blowing off steam is not being a spy.

For a lot of people, I think there was this silly expectation that all wrongs would be righted with a new administration. That’s obviously naïve, and this story is probably one example of that. Do you think people aren’t ready to hold the Biden administration’s feet to the fire?

Well, I think we can all agree and appreciate that the Biden administration has a pretty big list of stuff that they’re trying to fix and trying to undo. It’s important, whenever we can, to remind them of things that are important. Commuting Reality Winner’s sentence is a gesture that can be done with the stroke of a pen. It’s not a super challenging item on the docket. Of course, we will hold their feet to the fire. No one presidential administration does all the things you think they should do in exactly the way that you think that they should be done. The Biden administration is no exception.

I do think what differentiates them from the previous administration is that I don’t feel like they’re acting out of reasons of unabashed cruelty. I don’t think that they’re coming at their decision-making from the perspective of, “We should really fuck this up, mess with people’s lives and make them really scared.” So I’m very grateful for that. I’m so excited to not have to cover the Trump administration anymore. I get a little tickle in my tummy whenever I think about how they’re all gone.

What do you suggest people to do if they want to rally behind a commutation?

I understand that asking people to write letters is just about the most boring civic duty. I get it. “I don’t even have stamps. What are you talking about?” But those gestures, they actually work. They really do annoy our political leaders to the extent that they just give in. And I think out of anyone’s audience, my audience is the most likely to pen a sternly-worded letter and send it to the exact right person. This is a big deal. America was changed because of what Reality did, and I think that we owe her.

Not to make light of the situation, but you do touch on this in the piece. Reality smuggled the documents in her pantyhose. Did you ever get a sense of why, in 2017, a 25-year-old woman was wearing pantyhose to work?

It is the greatest mystery that anyone can take away from this piece. I don’t have any good answers for you. I have people on my staff who have barely even heard of pantyhose, let alone worn them. Pantyhose haven’t touched their flesh in their entire life, and I’m really happy for them. Pantyhose are so bad. I wasn’t even sure we could get a pair of to put in the recreation, but they still exist. Go figure.

Interview edited for length and clarity