If you’ve spent any time in the Red Key Tavern over the last decade, there’s a good chance you shared the space with Dan Wakefield. The author and journalist was a regular there, and even recorded radio shows from the iconic watering hole, which opened in Broad Ripple just one year after Wakefield was born in 1932.
Wakefield died on March 13 at the age of 91 in Miami, where he was living with his goddaughter, his attorney, Ken Bennett, said.
Thursday afternoon, Red Key Tavern owner Leslie Settle drank a glass of red wine in the corner booth of the bar — Wakefield’s spot — in honor of her most famous regular. The tavern played a key role in Wakefield’s 1970 book, “Going All the Way,” and was later featured in the 1997 movie adaptation starring Ben Affleck.
“I loved his love for Red Key Tavern — this was his spot. He was a generous guy and brought all his friends here,” Settle said.
From his barroom booth, Wakefield swapped stories with other regulars, fielded questions and admiration from fans, and shared the many lessons he’d learned throughout his storied life. His friends and protégés are certain that his legacy — and the lessons he shared — will live on.
Journalist Will Higgins: ‘Going All the Way’ on a bus
Higgins met Wakefield in the late 1980s when the writer, who was living in Boston, came to Indianapolis for a lecture. After reading “Going All the Way,” set in Indianapolis in the 1950s, Higgins suggested over a breakfast interview that the duo lead a guided bus tour of the city.
About six months later, the two sold tickets and drove people past several landmarks featured in the book — including his boyhood home, Crown Hill Cemetery and the Riviera Club. Wakefield had written about the club’s history of segregation against African Americans and Jewish people in “Going All the Way.”
“We packed the bus with people and they couldn’t get enough of it,” Higgins said of the 1988 tour. “You just had to give a microphone to Dan Wakefield, and he was off to the races, and people were thrilled.”
What started as a profile on Wakefield, turned into a friendship between the two writers. From 2016-2017, Wakefield and Higgins recorded a monthly WFYI radio show, “Uncle Dan’s Story Hour,” at the Red Key Tavern.
And Wakefield had no shortage of material.
A few years after graduating from Shortridge High School in 1950, Wakefield moved to Illinois to attend Northwestern University before transferring to Columbia University in New York City to work on an English degree.
There, the budding writer became friends with author, playwright and Civil Rights activist James Baldwin and journalist Gay Talese. In the Big Apple, Wakefield had a brief romance with author Eve Babitz, who also dated Jim Morrison of The Doors.
“He told me, ‘That’s my favorite year that I could never do again,’” Higgins said.
Wakefield wrote nearly 20 books and helped edit several others. When he published his first book, “Island in the City: The World of Spanish Harlem,” in 1959, Wakefield asked Baldwin for advice.
“James said, ‘That’s good, Dan, but don’t quit until you have a whole shelf full,’” Higgins recalled. “And he did it. A year ago, we were having a conversation where … he basically said he was near the end, and he was pretty content.
“He set out to do a lot and write a lot of books, and he had done it. He was ready to go.”
Sports radio host Jake Query: ‘It was not a leisure trip for him.’
As a young journalist for The Nation, Wakefield had a front-row seat to one of the most significant trials in modern history: the 1955 trial of two white men charged with the brutal murder of Emmett Till, a 14-year-old African American boy visiting family in Mississippi from his native Chicago.
The accused — Roy Bryant and JW Milam — were found not guilty. In the first paragraph of his story, the 23-year-old Wakefield captured the willingness of small-town Sumner, Miss. – and much of white America – to overlook the horrors and violence of racism to maintain their status quo.
“The crowds are gone and this Delta town is back to its silent, solid life that is based on cotton and the proposition that a whole race of men was created to pick it,” he wrote.
While covering the Till trial was one of the most important moments of his journalism career, Wakefield was haunted by the dichotomy of his career taking off following the brutal murder of a child.
Query, a sports radio host on 107.5 The Fan, met Wakefield through a friend. They first bonded over sports after Query helped Wakefield, a diehard Miami Heat fan, update an app to allow him to watch games on his phone.
However, it was a trip in March of 2022 to visit the Tallahatchie County Courthouse – where Wakefield covered the trial – that cemented their bond.
“I realized it was not a leisure trip for him, it was a dark trip down memory lane,” Query said. “He felt a lifelong obligation to speak to the atrocities that happened to Emmett Till, to uncover a justice that Emmett Till did not receive. He had an obligation to morality that he never worded, but he exuded it and displayed it.”
Red Key cook Pat Chastain: ‘He taught me how to age well.’
Along with guiding readers through difficult national conversations, Wakefield had a knack for helping people — writers or not — learn about themselves.
Chastain became friends with Wakefield in 2015. That year, Chastain led the effort to get a park at 61st Street and Broadway Road – a setting in “Going All the Way” – renamed after Wakefield. He wanted more Indianapolis residents to know and celebrate him.
The friendship that grew from there was one of the “greatest relationships” of his lifetime.
Wakefield and Chastain lived three blocks from one another until Wakefield moved to Florida in 2023. They hung out at the Red Key and shopped at the local Kroger, and Chastain viewed Wakefield as a mentor as well as a close friend.
“I’m not a writer, but he gave me a lot of guidance on life,” Chastain said on Thursday, while prepping that night’s food at Red Key.
“He was very open to learning new things, and he didn’t act like he knew everything,” Chastain said. “It wasn’t like hanging out with an old person. He taught me to remain open in life. I think that was the reporter in him – he was always looking for a new story. He taught me how to age well.”
More memories of Dan Wakefield
Karen Kovacik, IU Indianapolis director of English graduate studies and former Indiana poet laureate
In 2017, Wakefield spoke at a #WritersResist reading, organized by Kovacik and co-sponsored by the Indiana Writers Center – which was founded by her late husband Jim Powell – and PEN America.
Wakefield was set to protest the inauguration of former President Donald Trump and read poet Emma Lazarus’ “The New Colossus,” which is published on the base of the Statue of Liberty.
“He told me he wasn’t sure he could do it,” Kovacik said. “He couldn’t perform it without crying, in light of the anti-immigrant rhetoric of the president-elect. I told him that under the circumstances, tears would be appropriate. He ended up performing the poem that night with much feeling.”
Susan Neville, author and former English professor at Butler University
Neville met Wakefield in the 1990s, and he always visited Butler whenever she held a seminar on Kurt Vonnegut, his close friend and fellow Shortridge High School graduate.
“He had an extraordinary gift for friendship, and the number of people he met with for meals and conversations lasted until right before he died,” she said. “When he moved back to Indianapolis, we began having dinner at the Red Key every other Tuesday, where we’d talk about books and writing and friends. In the last year or two, he’d taken to calling me his ‘soul sister,’ a memory which I’ll cherish.”
Nora Spitznogle, waitress at Red Key Tavern and friend
“I waitress there on Saturday nights, and it’s fun to tell people about him and see them Googling his name. He’s inspired a whole group of readers and writers. . . people are doing some reading they might not be doing otherwise. He was never that, ‘Look at me – I’ve had all these bestsellers.’ He was always happy for everybody.”
Julia Whitehead, CEO of the Kurt Vonnegut Museum and Library
During VonnegutFest in 2022, to commemorate what would have been Vonnegut’s 100th birthday, Wakefield spoke with a group of children about writing.
“He loved to just not be that professor or scholarly person,” Whitehead said. “He wanted to learn from other people. It’s one thing to be with him in Red Key Tavern and hear his stories, but it was a completely different experience to watch him with young people, engaging in storytelling and asking questions to understand another person’s life.”
Mirror Indy reporter Breanna Cooper covers arts and culture. You can reach her at breanna.cooper@mirrorindy.org. Follow her on X @BreannaNCooper.
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