A conversation with Seth Wickersham on his new book, Tom Brady, and life in West Hartford.

By Melissa Cole

“One of the best sportswriters of his generation. Maybe the best.” 

That’s how ESPN’s Wright Thompson describes his colleague Seth Wickersham in the foreword to Wickersham’s new book, Be on That Hill: Stories from the Summits of Sport, hitting shelves this month. 

This is Wickersham’s third book, an anthology that brings together some of the best sportswriting, investigative reporting, and storytelling from his 26-year career.

But did you know this ESPN senior writer and New York Times bestselling author lives right here in West Hartford? Wickersham and his wife, Alison Overholt, whom he met while working at ESPN Magazine, moved to town in 2014.

“It’s its own community,” he said. “And I really like that it has its own identity. People are here for a reason – it’s not just because it’s near the city. I like that there’s a great combination of transplants and people who grew up here, and they’re attached to the community in a real way.”

He also has a soft spot for the local ice cream. “A.C. Petersen’s vanilla ice cream – seriously, have you ever had better vanilla ice cream than that?”

The couple has since put down roots in West Hartford, where they’re raising their two children. Their son attends Wolcott Elementary School, and their daughter is a sophomore at Conard.

But his own childhood looked quite different. Wickersham was born in Denver, lived in Boulder until 1983, and then relocated to Alaska, where he lived until college.

“My parents met here in Connecticut, randomly,” he said. “My dad was in law school at Yale. My mom was an undergrad at Bridgeport. They moved to Colorado. He’d gone to undergrad at the University of Alaska and always wanted to go back. I guess the mountains weren’t big enough in Colorado for him, so we moved to Alaska, and that’s where I went through high school.”

Wickersham’s love of journalism started early. He fondly remembers reading the newspaper with his dad, being curious about how stories were put together, and how some stories seemed to stand the test of time. He joked that he earned a letter in his high school newspaper before he did in sports.

Fast forward to college: he studied journalism at the University of Missouri, had a series of internships, and also wrote for the community-based newspaper, The Columbia Missourian. He’d occasionally get the opportunity to cover NFL games. 

During Wickersham’s senior year, the St. Louis Rams made it to the Super Bowl, and he and a friend from the paper had an idea.

“Wright Thompson, who works at ESPN with me – you know, brilliant writer – had the idea to apply for credentials to the Super Bowl,” he said. “We got accepted, and we went. It was like spring break for nerds. It felt like we were crashing an exclusive party.”

While he was in Atlanta for that week, Wickersham had a moment that would foreshadow the rest of his career.

“When I was there, I crossed paths in the media center with this guy named John Papanek, who was editor-in-chief of ESPN Magazine. I recognized him, and I introduced myself, and I noticed he was letting a lot of young writers write for his magazine. I was like, I want to be one of those guys one day.”

And soon after, he was one of those guys. Wickersham was hired at ESPN Magazine pretty quickly after graduating from college, writing feature pieces and investigating some of the biggest stories in sports over a two-decade span. His new book, Be on That Hill, is a culmination of all of it.

“I wanted it to have a cumulative purpose and theme and arc,” he said. “And so I picked stories that I thought told the arc of the last 25 years in sports.”

Readers will find sports stories, and stories beyond sports, about lesser-known athletes and more notable ones like Patrick Mahomes, Bill Belichick, Sean McVay, Sean Payton, and Tom Brady, who, he said, he had a friendly professional relationship with.

“We both graduated from college in 2000. ESPN Magazine sent me to Foxborough in 2001 to write about this skinny quarterback who was filling in for Drew Bledsoe,” he said. “We were both young men getting our career breaks at the same time. And then his life changed fast.”

Over the years, Wickersham caught up with Brady at nearly every stage of his life.

“There were moments where I met up with Tom when he was single, and there were moments after he was married, and then when he had kids and he was a young father. There was a story I did on him once – he told me to come to his apartment in Boston. I’ll never forget: the elevator door opened right to the living room.” 

That meeting was during a pivotal moment in Brady’s career.

“He was a little bit at a crossroads in his career. And I’ll never forget, he said, ‘My first 10 years in the league have prepared me for my last 10.’ And I was like, what? His last? Who says stuff like that? But that’s who he was. Whenever he was doubted, he upped the ante on everything. And he lived up to it.”

You can hear more from Seth Wickersham himself, and pick up a copy of his new book, at “An Evening with Seth Wickersham: Be on That Hill,” hosted by River Bend Bookshop in West Hartford, CT.

The event takes place Friday, Oct. 9, from 6:30 to 8 p.m., and will be moderated by Wickersham’s wife, Alison Overholt. Overholt is an award-winning media executive, producer, and editor. She was the first woman to run a major U.S. sports magazine when she became editor-in-chief of ESPN The Magazine, leading the brand to a National Magazine Award for General Excellence.

More information and registration information can be found here.

At the end of our interview, when asked about being called perhaps the best sportswriter of his generation, Wickersham modestly said this:

“I just hope that whenever I walk away, people look back at my career and say, ‘He added to this collective of great sportswriting.’ Hopefully the book is a little piece of that.”

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