Ben Montgomery is the author of “The Man Who Walked Backward: An American Dreamer’s Search For Meaning in the Great Depression.” The book was published by Little, Brown Spark in September, and tells the story of a man named Plennie Wingo, who in 1931, attempted to walk around the world, backward.

This is the third time Montgomery has been on the podcast. He was the guest on Episode 21, when he talked about his first book, “Grandma Gatewood’s Walk: The Inspiring Story of the Woman Who Saved the Appalachian Trail.” That book went on to become a New York Times Bestseller.

He was also one of five guests on Episode 45, which was focused on the work of the late Michael Brick, which was contained in the book, “Everyone Leaves Behind a Name.” The other guests on that show were Wright Thompson, Michael Kruse, Tony Rehagen, and Thomas Lake. 

Montgomery created the website gangrey.com, which was the namesake for this podcast. For years, he was one of the top enterprise reporters at the Tampa Bay Times, where he wrote about everything from the last spectacle lynching in Florida to why cops shoot at suspects. 

He left the Tampa Bay Times in October 2017 to focus on writing “The Man Who Walked Backward.” Now, he finds himself teaching student journalists at the University of Montana as the T. Anthony Pollner Distinguished Visiting Professor. 

Montgomery’s latest book is his third. His second book was titled The Leper Spy: The Story of an Unlikely Hero of World War II. 


He was a finalist for the Pulitzer Prize in Local Reporting in 2010 for his series of stories on the decades of abuse at a Florida reform school for boys. He won the Dart Award and Casey Medal for the same series.

Episode 67: Ben Montgomery

On this episode, I’m going to replay an interview I did Wright Thompson back in October of 2013. 

Thompson’s first book was just released by Penguin Books this week. It’s titled "The Cost of These Dreams: Sports Stories and Other Serious Business." It consists of 14 of Thompson’s previously published stories for ESPN. That includes the two stories that I talked with Wright about on this episode of the show – "Michael Jordan Has Not Left the Building," and "The Losses of Dan Gable." 

Thompson’s profile on legendary wrestling coach Dan Gable is a perfect example of how and why reserved people open up to him. 

The Dan Gable story came up right on the heels of Thompson’s profile of NBA legend Michael Jordan. That’s the story that leads of the book. With the Jordan story, Wright said he kept thinking of the classic Esquire profile on Ted Williams, which was written by Richard Ben Cramer. That story was titled “What Do You Think of Ted Williams Now.”

“That story is very much a North Star, and the thing I’ve always wanted to do, always, is write that story,” Thompson says. “I knew going in that they’re only a couple of athletes famous enough to make that even possible.”

The book is fantastic, of course. And it’s no surprise to me that after one week of sales, it’s already showing up at No. 4 on the New York Times Best Seller list for paperback nonfiction.

Wright Thompson (2013)

Gangrey: The Podcast focuses on narrative journalism and the reporters who write it.

Wright Thompson (2013)

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