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Mitchell S. Jackson on ‘Fly: The Big Book of Basketball Fashion’ and His Writing Journey

The erstwhile Portland author's new book shows how today's professional basketball stars influence fashion, style and more.

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Mitchell S. Jackson
Mitchell S. Jackson. Photo: Christa Harris.

This past July, Boston Celtics forward Jaylen Brown signed the richest contract in National Basketball Association history to date for five years, $303.7 million. He followed the signing by proclaiming he wanted to invest some of that money into building a new Black Wall Street in Boston, a reference to the Black economic hub that was established in Tulsa, Oklahoma and then burned down by white mobs in 1921.

When author Mitchell S. Jackson saw this statement, he couldn’t help but recall another landmark sports moment that happened off the field: The Cleveland Summit in 1967 where star professional athletes Bill Russell, Kareem Abdul Jabbar, Jim Brown and others, all dressed in suits, joined Muhammad Ali for a press conference where Ali explained his refusal to enlist in the military and his opposition to the Vietnam War.

“What if the Cleveland Summit had social media?” Jackson muses. “Those guys were also really fashionable players. I think fashion and activism have always been a part of pro sports. 

“Now what we’re seeing is that players have more awareness. Social media has not only given them platforms to become brands, but has also given them more awareness. We’ve got a combination of more awareness, a bigger platform for athletes and more money and power.” 

His latest book Fly: The Big Book of Basketball Fashion explores the spotlight that NBA players command and how these predominantly Black athletes have and continue to leverage their power and influence. The coffee table book is part lookbook, part cultural commentary, delving into the style and politics of each era of the NBA from its beginnings in 1949 to the present, which Jackson describes as “a time defined not only by social media and high fashion’s birthing of the tunnel walk (think LeBron James, Dwyane Wade, and Russell Westbrook) but one in which athletes are idealized as style icons and activists, figures who inspire conversations beyond how they play and what they wear.” Jackson will talk about the book in a public event at downtown Portland’s Powell’s City of Books on Wednesday, September 20.

Writing about the athletes who inspired him by leveraging their sports celebrity to benefit their communities is a theme that dates back to Jackson’s earliest published writings. These figures continue to influence his work now as he builds his own fame.   

From ‘Almost Famous’ to National Accolades

Jackson, a Jefferson High School standout who went on to play junior college basketball, has long been fascinated by the sport’s intersection with spectacle and influence. His first published piece, which appeared in the Portland Tribune in 2001, was called “Almost Famous” and centered on the stories of Portland basketball legends who didn’t make it to the NBA. The hoops contemporaries he profiled for that story, Patrick Strickland, Antoine Stoudamire and Orlando Williams, have all since made imprints on the city through, among other things, coaching, music and Portland Trail Blazers broadcasting, respectively. When writing “Almost Famous,” Jackson realized Strickland, Stoudamire and Williams would find success one way or another because their talents outside of basketball could take them down a variety of career paths.  Similarly, when Jackson’s basketball career ended, he maintained his tunnel vision, but transitioned it to writing.

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“Either I was gonna make it or I was gonna make it,” he says.

Fast forward to 2023. With a Pulitzer Prize, Ernest J. Gaines Award for Literary Excellence, and TED, Lannan Foundation and Guggenheim Fellowships under his belt, Jackson has indeed “made it” by all metrics. 

Yet the path has been anything but linear or smooth. In the 1990s, Jackson was incarcerated for drug charges after getting into minor drug dealing while trying to figure out life after basketball. While writing had long been a hobby, Jackson began seriously delving into autobiographical writing during his incarceration. As he noted in an interview we did for The Skanner for the release of his debut novel The Residue Years, he wanted to tell his own story more accurately than the hackneyed versions of his experience, and by extension the “Black experience,” that he saw in popular media. Initially, he pursued a career in broadcast journalism, but while interning with local TV news stations, he found that TV didn’t allow him to explore and express his thoughts with the depth he desired.

Jackson published his first book, Oversoul: Stories and Essays, in 2012 and followed that with The Residue Years in 2013, which received many honors, including the aforementioned Gaines Award. His 2019 book, Survival Math: Notes on an All American Family, was recognized on best-of-the-year lists by Time, National Public Radio and Buzzfeed, and his 2020 profile of Ahmaud Arbery for Runner’s World won the National Magazine Award for Feature Writing. He has also taught in universities throughout the country, and currently serves as the John O. Whiteman Dean’s Distinguished Professor in the Department of English at Arizona State University.

Author vs. Writer

Despite the success, Jackson doesn’t have a hard time maintaining humility and professional hunger. A writer’s fame is different from that of other celebrities. “Paparazzi are not following around writers,” he says.

Sometimes this leads to situations, especially when it comes to press outside the writing world, where Jackson finds himself not just promoting his work, but also pushing back against the devaluing of writers.

“You’ve got to move them [the press] out of the space of thinking they’re doing you a favor,” he says.

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For Jackson, this is just part of the work of separating being an author from being a writer. The latter encompasses the actual act of writing. Being an author, meanwhile, is the work of doing interviews, lectures, panels and other activities talking about the writing. Finding a balance between the two is a constant practice, he says.

When it comes to author-related activities, Jackson stays grounded in Portland. In 2013, he co-directed, wrote and produced a documentary based on The Residue Years, which includes footage from him visiting and speaking with men in the same prison where he was once incarcerated. He has contributed to and been featured in various projects highlighting the history of Northeast Portland and Black community in the area, such as the Alberta Street Heritage Markers

Mitchell S. Jackson's "Fly"

Jackson also regularly participates in conversations and activities with local media and literary organizations, such as Literary Arts (including an appearance at its annual Portland Book Festival on Saturday November 4) and Oregon Humanities. “Oregon Humanities has had the good fortune to work with Mitch in a few ways over the last several years,” says OH Executive Director Adam Davis. “He’s been a Consider This guest, written for Oregon Humanities magazine, and been on The Detour podcast. In every instance, he’s brought his unique combination of intelligence, humor, candor, and warmth. Jackson also has deep experience with and understanding of Portland, and he’s got crackling takes on the place and the people who live here. Even if Mitch isn’t in Oregon right now, he’s an Oregonian, and Oregon is much the better for that.”

One of the ways he makes Oregon better is through giving back to students and aspiring young writers through activities like speaking at Portland schools, including King Elementary where he attended as a child, and participating as a judge in Literary Arts’s Verselandia competition. He has also never been shy to offer informal advice and insights to up-and-coming writing professionals (author’s note: including this writer). Jackson takes special pride in giving back to and providing guidance to aspiring writers of color in general and young Black writers in Portland in particular. 

Following the example of the superstars behind the Cleveland Summit, his peers featured in “Almost Famous” or even young athletes today like Jaylen Brown, Mitchell Jackson treats leveraging his success to support his community as an expectation. 

“Everything I write is for my people,” he says. “You’d be a sucker to keep it all to yourself.”

Mitchell S. Jackson will be in conversation with Tra’Renee Chambers and signing copies of Fly: The Big Book of Basketball Fashion at Powell’s City of Books in downtown Portland on September 20 at 7 pm.

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Bruce Poinsette
Bruce Poinsette is a writer, educator and radio host whose work is primarily based in the Portland Metro Area. His writing has appeared in various publications, including The Oregonian, Street Roots, Oregon Humanities, and Eater Portland.
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