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Writer, podcaster, TV host Charlotte Wilder is the new face of sports media

By Gerry Boyle ’78
June 13, 2019

I’m sitting at a window table in Seamore’s, a relaxed R&B-on-the-playlist seafood place in Nolita in lower Manhattan, waiting to start a late lunch with Sports Illustrated writer/podcaster/TV host Charlotte Wilder ’11. It was a cold walk down from midtown so I’m sipping coffee, waiting for Wilder to stroll through the winter-curtained door like a James Corden guest when, instead, my phone buzzes.

It’s a text from Wilder. She’s on her way from Brooklyn. Sorry, she types, had to publish a big story and got a little caught up …

So I tap the phone and, sure enough, there’s the story, freshly posted. It’s about the former (as in fired) NFL coach Jeff Fisher and what he’s been up to, other than being the butt of running jokes about football mediocrity. Wilder starts it like this: Jeff Fisher is careening down the side of a very steep hill on his ATV in the middle of the Tennessee woods. I’m sitting on the back, holding onto the machine for dear life. … “Feet up, Char!” Fisher yells.

In the world of professional sports, it is a big story, a perceptive and sympathetic portrait of a big-time NFL competitor and his life in forced exile. It’s also about the fickle nature of success, something of which Wilder—having landed one of the best sports-media gigs in the country at 29—is well aware.

“This time last year I was still terrified that this would go away,” she says. “Watch me get fired for something tomorrow after I say this, but I think I’m finally in a place where I’m like, ‘OK. This has staying power.’”

Wilder says this after pushing through the curtained restaurant door, but not like a talk-show guest. In jeans, low white Adidas, and a puffy black jacket, she looks more like a day-off young professional late for lunch with her dad, visiting the big city from Maine. But then, she doesn’t look or seem much different from the Charlotte Wilder on TV. Down to earth. Funny. Straightforward. Confidently self-effacing. Somebody a recently big-time NFL coach would ask, “Do people call you Char?”

The answer would be yes.

“I think people can relate to authenticity more than anything,” Wilder said. “And I think what I’m doing now is the same thing I did when I had like two-hundred Twitter followers and was sitting in my parents’ basement and no one knew who I was.”

They do now.

At 29, Wilder is a senior writer for S.I. (one of the youngest ever), penning long-form stories on everything from Fisher to the demolition derby at the Union (Maine) Fair. She’s a popular podcaster (Most Valuable Podcast) with partner Jess Smetana, a constant Twitter presence (@TheWilderThings has nearly 38,000 Twitter followers), and host of a weekly Sports Illustrated TV series called The Wilder Project.

The second season launches this month. Her agent at Creative Artists Agency negotiated the deal. Are you starting to get it?

“She is basically a walking content-creating machine,” said Josh Oshinsky, executive vice president and head of video programming and content strategy for Sports Illustrated. “She really is a confluence of what today’s modern media landscape is, with a personality that’s just suited for it.”

That she is. Just one example. Eight days in Atlanta for Super Bowl LIII yielded:

A personal essay on the Patriots’ dynasty.

“Whenever the Patriots take the field, my subconscious takes over and I’m a goner. I become like one of those goslings from the experiments Konrad Lorenz used to run when he wore red boots and marched around the yard scattering food. The goslings would imprint on the red boots and be drawn to them for the rest of their lives. The Patriots are my red boots. I am powerless against this team.”

Charlotte Wilder ‘11 at Superbowl LIII for Sports Illustrated
Charlotte Wilder ‘11 at Superbowl LIII for Sports Illustrated.

A stream of tweets (“If one of these teams scores a touchdown I’ll send them an Edible Arrangement”), video for social of Tom Brady walking into the locker room with the Lombardi Trophy (35,000 views), a podcast (“We’re alive after the Super Bowl”) with guests Kansas City Chiefs tight end Travis Kelce and Houston Texans quarterback Deshaun Watson.

“It’s been a wild ride,” Wilder said on Twitter upon her return to New York.

Wild and unlikely? I mean, not so long ago Wilder was a history major/creative writing minor at Colby, co-winner of the Mary Low Carver Poetry Prize. That she would work her way to national sports-media prominence, mingling effortlessly with celebrity athletes, blitzing her social media audience with Wilder murmurings, writing polished and pointed stories on everything from the NBA to air guitar, chatting with the camera like it’s an old friend? Remarkable.

Yes and no. For Wilder, it’s all part of a continuum, albeit one that’s tipped steadily upward like the graph of a bull stock market. The poet at Colby and the slinger of tweets are different facets of the same person, one who is vigilantly observant, self-aware, and driven to capture the world around her in words. Spoken. Measured in characters. Carefully crafted in stories that beguile readers for pages.

“The heart of my show is verbal,” Wilder says. “We write bits for the podcast and we have fifteen-page Google docs for each show. … Writing is at the core of everything I do and writing is always the thing. I get such a high.”

That may be partly genetic. Wilder’s mother—and occasional writing sounding board—is Deborah Weisgall, a novelist and memoirist who has written about the arts for the New York Times and The New Yorker, among others. With that pedigree, Wilder arrived at Colby more interested in poetry than sports.

Adrian Blevins, associate professor of English, remembers her as part of a powerhouse class of student poets—Blair Braverman ’11, Molly Bennett ’11—who competed with each other, poem by poem, line by line. Contacted for comment for this story, Blevins dug into her files and reviewed a batch of Wilder’s work.

“I really like these poems,” Blevins reported back. “…They describe states of aloneness … and are a little about exile, too. The speaker is trying to figure how where she is/fits into the world.”

And in that group, Wilder stood out for another reason. “She was always argumentative, in a useful way,” Blevins said. “She would say, ‘But is that really true?’ She wasn’t compliant.”

Not then. Not now.

“Colby was hugely influential for me,” she says. “I didn’t go to journalism school. I come at prose with a much more poetic approach, where it doesn’t have to follow rules.”

But it isn’t so much that Wilder flagrantly flouts journalism’s conventions (she’s a gifted storyteller), as much as she infuses her prose with images that lift the story off the page. Like this paragraph from her S.I. story about the demolition derby at the Union Fair, a subject which in itself stretched the bounds for a sports magazine. Here’s how she describes the way a tow-truck driver named Jacoby Leavitt preps a car for the derby:

Sparks fly, then he rips the bumper the rest of the way off with his hands. He’s stripping the car the way he guts a deer. Leavitt loves to hunt, and this year he finally got approved for a moose license. It’s almost surgical, the way he pulls out wires like they were intestines, strips the plastic off the doors as though it were the skin covering a deer’s muscles.

Sports Illustrated Executive Editor Steve Cannella noticed Wilder when she was writing for SB Nation, the way she participated in her stories but not in an obtrusive, distracting way. “Charlotte is the reader becoming part of that story,” Cannella said. “As a reader, you’re living, breathing, seeing, smelling, tasting exactly what she is. That’s what you want to do. You want to take the reader where you are. … She’s executed that in spades.”

The ability to bond with an audience is something that’s tough to teach. In fact, the key to Wilder’s success is in large part to continue to be, well, Charlotte Wilder. Oshinsky and Cannella had an overarching piece of advice when they brought her on: “Don’t change your voice.”

It’s advice that Blevins, the poet/professor back at Colby, understands. Rereading Wilder’s poems, she came to this conclusion. “They’re pretty narrative, but the images are doing most of the work. I love the imagery best, but also the voice: here’s a speaker you can trust.”

Readers, listeners, viewers, Jeff Fisher in the Tennessee hills—they trust Charlotte Wilder.

Her persona—in her stories, on TV, on her podcast—is that of a very knowledgeable and inquisitive reporter, an attentive listener, someone who is empathetic, understanding, and real. She has an innate ability to go to the readers/listeners/viewers, rather than forcing them to come to her—key in a world where content is consumed 24/7.

I say as much and Wilder is graciously appreciative. But she knows she’s skilled and has known that for some time, back to when she was breaking into sports at USA Today. “I knew how good I could be, but I knew I had to prove it. I knew I had to work my ass off to get recognized.”

In fact, she was very quickly recognized, and by people with clout in the industry. She was a tender just-turned 29 when she arrived at S.I. as a senior writer, among other things. “I’ve worked so hard, so much, and I’m good. Age isn’t a marker of ability.”

Wilder also is very much aware that’s she’s risen through the ranks in a traditionally male world that is focused, for the most part, on professional sports teams made up of men, coached by men, rooted on by men. In the world where she now operates oftentimes women are seen as just that—women, first and foremost.

“I don’t want to be defined that way,” she says. “I want to be that person who is doing a good job. I happen to be a woman. That makes some things harder and some things easier.”

“The heart of my show is verbal,” Wilder says. “We write bits for the podcast and we have fifteen-page Google docs for each show. … Writing is at the core of everything I do and writing is always the thing. I get such a high.”

On the podcast, Wilder says, she and Smetana are “just talking about sports. We never make a big deal of the fact that we’re women, but we’re existing in that space to show that you can be there.”

Wilder does hear from college-age women who thank her for just being there. Remembering a time not so long ago when she was reaching out for advice and any response gave her a much-needed boost, she responds. “A lot of women will reach out to me on Twitter with DMs, or Instagram or email me and I really try to make a point to hop on the phone with them. I don’t ever want to be too busy.”

There are limits, though. Once Wilder, on camera on The Wilder Project, offered to advise women on how to break into sports media and she got more than 600 Twitter messages in a single day. That necessitated some blanket advice during the next episode.

Over lunch, she dispenses that advice again: “I think the biggest thing is make yourself responsive. Be enjoyable to work with. You might take a job where you’re like, ‘This isn’t what I want to do.’ If it’s at the right place, if it gets your foot in the door, do it. And network constantly. This business is so much about who you know. So reach out to people, send them your stuff, make people remember you. Build connections and relationships because that’s the web of this industry. Publications are so unstable now that people are loyal to people.”

She pauses and adds: “And just work. Work so hard.”

Just like Wilder still does.

“She was down in Atlanta for eight days,” Cannella said. “She was working nonstop, probably twelve, fifteen-hour days. Twelve hours after she got home she was in my office saying, ‘I gotta find a story!’ and pitching another five or six ideas.

“Not only is her mind always working. Her mind needs to be working.”

So just as it was her work ethic, in part, that got Wilder to where she is, she’s keenly aware that it’s her work ethic that will, in part, keep her there. With the byline. The TV show. The podcast. The social media following. Yes, the celebrity.

Not that Wilder considers herself one. That day in the restaurant nobody comes over to ask if she’s Charlotte Wilder. But more and more, at sports venues, it’s a different story.

A quick example: when she was covering the 2018 World Series, a man approached her and asked her to sign his baseball. Wilder thought maybe he was an oddball, just approaching random people. “I’m like, ‘Why?’ He says, ‘I really like your work.’ I said, ‘Oh, wait. So you know who I am?’ He’s like, ‘Yeah, you’re Charlotte Wilder.’”

Was she creeped out? “I love it,” she says. “It means I’m going to have a job still. Maybe.”

“All of this is a foundation for what this can become,” she says, with a strategic matter-of-factness. “I don’t know what that is yet. I’m really happy because I’m still learning, I’m being challenged constantly. I think the sky’s the limit.”

Success doesn’t always beget success, and in sports media meteoric rises can be followed by precipitous falls to earth. Maybe for that reason, up-and-coming Charlotte Wilder has that energized restlessness that you see in people who have big chunks of talent and ambition and a propensity for hard work. They’re like sharks. If they stop moving, they die. Well, maybe not die. But they certainly don’t thrive.

Wilder’s upcoming itinerary is frenetic, including a trip to Arizona for a big story that she can’t talk about, not to mention the Super Bowl. And there’s the podcast. And Twitter. And the second season of The Wilder Project readying for kick off in March. And yet, just to complicate things more, amid the blur Wilder also knows that to be good at her craft requires her to brake hard, take a step outside of herself.

Listen very closely to Jeff Fisher in the Tennessee hills as he slowly reveals his disappointment, his resignation, his still-smoldering hopes and dreams. Really understand the life of the demolition derby guy in Maine, play with his kids, hear the sounds of their young lives. Be aware of a sports star—fill in the blank— guest’s verbal cues so you’ll know where the conversation is going, where it can be steered, when that uncomfortable must-ask question can be dropped. Trust your instincts. And oh, yeah. It has to be good.

Wilder is acutely aware of the damage bad work can do. “It either causes a huge hubbub and then you’re screwed. Or it’s boring,” she says. And boring also means you’re screwed—albeit like a dying bonfire rather than a fiery crash.

She has no intention of doing either. “All of this is a foundation for what this can become,” she says, with a strategic matter-of-factness. “I don’t know what that is yet. I’m really happy because I’m still learning, I’m being challenged constantly. I think the sky’s the limit.”

And with that, Wilder’s internal alarm goes off. She looks down at my watch, sees that it’s 3 o’clock, and the time allotted for the interview does have a limit. She has an appointment uptown, which seems fitting to the angle of her trajectory.

Wilder puts on her jacket, hugs goodbye, heads for the door. I watch from the window as she leans into the wind and heads up Broome Street. Charlotte Wilder, after all, has places to go. She’s in a hurry.