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Getting his reps in: Richard Jefferson’s second act

Mark M. Wright

25 Jan 2021

Even before he took his first shot in the NBA in 2001, Richard Jefferson had a plan for life after basketball, looking ahead for a post-playing career in media and entertainment.

As his longtime friend, lawyer Robert Maylor, recalls: “Early on, Richard [said], ‘Rob, you’re going to be my lawyer [and] you got to be my entertainment guy who makes sure I’m doing the right thing.’”

Fast forward two decades, and Jefferson’s plan has come together. He, of course, handled the basketball part: Seventeen years in the league playing for eight teams, winning an Olympic bronze medal and — of course — an NBA championship in his fourth attempt, alongside LeBron James and his good friend Channing Frye, in 2016.

Along the way, the Los Angeles native raised in Phoenix became an early adopter of social media, something he parlayed into a successful podcast called “Road Trippin’” that he launched in January 2017. It holds acclaim as the longest-running, player-hosted podcast, topping best-of podcasts lists across the U.S., having amassed more than 6 million downloads globally.

Now a seasoned pro in media — three years retired from playing — Jefferson’s self-deprecating and wise-cracking style is also seen and heard across ESPN platforms as a color commentator; he’s also an analyst on the show “NBA: The Jump” with Rachel Nichols, who covered Richardson during his Nets days.

And Jefferson is into his latest media move, a show on YouTube called “The Sports Gap” that launched last year from the NBA bubble in Florida. He describes it as a sports satire show at the intersection of pop culture, music and politics.

Explains Jefferson: “Athletes are activists, athletes are musicians, and even though they might have always embraced those roles, with social media and with the way things are being covered right now, there’s not a space where you can go and see a summary of how sports has intersected with everything, over the course of a given week or given month.”Early ambition

Jefferson played in college at Arizona and landed with the New Jersey (now Brooklyn) Nets, who took him with the 13th pick in the 2001 NBA draft.

For Jefferson, his time in the NBA wasn’t just about catching lobs from Jason Kidd — and reaching the NBA Finals (which he did twice with the Nets, 2002 and 2003, losing both times). Jefferson was eying his long-term plan, beyond hoops.

While still a player, he attended the NBA’s Sportscaster U. on-air boot camp at Syracuse University. And while playing in Cleveland, he had his own segment with Cavs’ TV play-by-play man Fred McLeod during Fox Sports Ohio’s postgame coverage.

The launch of the “Road Trippin’” podcast in 2017 provided his first real opportunity to become a respected media personality.

“I really wanted my second act to be something that I wanted to do and be more creative — whether it was doing a Snapchat, or ‘Road Trippin’,” said Jefferson, who believes the podcast was the first of its kind started by an active player during his season.

Whether it’s “All The Smoke” (with former NBA players Matt Barnes and Stephen Jackson), “The Pat McAfee Show 2.0” or “The JJ Redick Podcast with Tommy Alter,” there is a preponderance of jocks waxing unapologetically on all things sports, culture, music and — particularly in this time of racial and social unrest — politics.

Jefferson’s “Road Trippin’” includes Frye, Richardson’s former teammate with the Cavs, and host Allie Clifton, formerly the Cavs’ sideline reporter. The trio hosts what often sounds like a weekly play-date with their athlete friends, talking honestly and freely about everything, and anything.

“Road Trippin’” was born out of frustration with how professional athletes are covered and portrayed in the fast-moving digital age.

“So many times the player narrative [is] driven by the media,” Jefferson explains. “Me, LeBron, Kevin Love, Channing Frye, and the [Cavs] entire team would sit down and drink wine and have dinner after a game, and we’d be laughing and joking, telling stories. And then, you’d open up the newspapers the next day, and it’s like, ‘LeBron didn’t shake Kevin Love’s hand — there’s a rift going on.’ These individuals aren’t seeing what we’re seeing. I think once players figured out that they could tell their own stories via podcasts or long-form conversations, things blew up.”

Get To Know: Richard Jefferson ■ Age: 40 ■ Residence: Hermosa Beach, Calif. (born in Los Angeles, raised in Phoenix) ■ Family: Wife Afra; two children, Richard Jr., 5 and Phoenix, 3 ■ College playing career: Arizona Wildcats ■ NBA playing career: 2001-2018 (New Jersey Nets; Milwaukee Bucks; San Antonio Spurs; Golden State Warriors; Utah Jazz; Dallas Mavericks; Cleveland Cavaliers; Denver Nuggets) ■ NBA Finals appearances: 4 (two with the Nets; two with the Cavs) ■ Olympics: Bronze medal, 2004 Summer Olympics ■ Sports media career: “Road Trippin’” podcast (launched 2017); analyst on “The Jump”; studio and game analysis for the Pac-12 and YES networks; “The Sports Gap” (launched last year)

By Episode 28 — just shy of five months after the show’s launch — “Road Trippin’” would log a No. 1 ranking on’s US Sports & Recreation Podcasts Top 40 Chart (Love was the featured guest). They’re up to 140 episodes now, with Dwyane Wade and James among the latest guests.

Clifton (along with Jordan Harris, recently hired as manager for “Road Trippin’”), runs point on marketing, advertising and sponsorship for the podcast, with past ad support coming from the likes of State Farm, Patrón, sleep product maker Casper and food service company Blue Apron.

“Seeing Richard evolve has been amazing,” said Frye, himself a well-traveled former Arizona Wildcat who played for six teams over 13 seasons, before retiring in 2019. “He’s constantly evolving, too. For “Road Trippin’’’ to still be around is pretty amazing.”

“Road Trippin’” can be found on all podcast outlets (as well as on its YouTube channel) and isn’t part of a podcast network.

Sports fans have further gotten to know Jefferson from his work on ESPN platforms including “NBA: The Jump.”

“What makes him so valuable to us on ‘The Jump’ is the fact that he can speak to [being in] so many different situations — he knows what it’s like to be a star player on a team in the Finals; and knows what it’s like to be a role player on a title team, so he really helps us from so many different perspectives,” show host Nichols explains.

LeBron James sat for an episode of “Road Trippin’” while former teammate Channing Frye joined remotely."ROAD TRIPPIN'"

Finding his niche, while filling the gap

While Jefferson continued to hone his craft — calling games for the Pac-12 and YES Network — the one-time NBA Slam Dunk contestant chiseled away at an idea he felt would fill a void in sports: a sports satire show.

Over the course of two years, Jefferson and Maylor — along with a few trusted media friends, including Roy Wood Jr. from “The Daily Show” — sketched out a television show. Initially, the two came up with a concept called “Unfiltered,” and shot a pilot, bankrolled by Jefferson.

“We’d gotten to the finish line, with a lot of different networks, and finally, I was like, ‘Yo, you know what, instead of trying to sell it to people, I’m just going to do it and do it on my own and see what happens,’” said Jefferson.

Stuck in the NBA bubble while working for ESPN during last season’s postseason, Jefferson — with Maylor as his head writer — dropped the first of three episodes, all 10-15 minutes in length and available on YouTube. Episode 1 of the show they would call “The Sports Gap” opened with Jefferson talking about athletes using their platforms to affect social change; ripped talking head Skip Bayless for questioning Dak Prescott’s leadership when the star quarterback spoke out about his mental health in the wake of his brother’s suicide; and shamed fired radio host Dan McNeil after he tweeted a sexist and misogynist tweet about ESPN reporter Maria Taylor.

Jefferson won an NBA championship in Cleveland as a teammate of LeBron James.GETTY IMAGES

Jefferson isn’t afraid to call people out; still, “The Sports Gap” is far from a show that just has hot takes on hot topics. It’s a well-researched collection of stories, and Jefferson comes across as credible.

“That’s part of the method to his madness,” Nichols said. “He does project a lot of fun but don’t let that fool you — he is one of the most prepared people I have worked with and he wants to do well, and he cares.”

Maylor and Jefferson have dropped 10 episodes in total. Maylor continues to field calls from potential media platforms and sponsors with the goal of growing the show. Meanwhile, Jefferson continues to financially back the show while exploring the right partnership for broader distribution.

Jefferson, in the last year of his first ESPN broadcasting deal working across multiple platforms, will continue to push the envelope on a platform he can truly call his own.

Meanwhile his “entertainment guy” — Maylor, who graduated law school in 2005 and film school in 2014, is also a producer and screenwriter — has Jefferson thinking bigger, and broader.

Jefferson, 40, is game: He’s added executive producer to his CV — having partnered with Maylor on the 2018 film “Sprinter,” about an up-and-coming Jamaican track star. Jefferson so believed in the project — which was also executive produced by Will Smith and Jada Pinkett Smith — that he wrote a $500,000 check to start production on the film without much prodding.

“He jokingly said right after the 2016 [championship] that he was going to retire — but he didn’t; he was just being a troll,” Maylor explained. “But he was honestly thinking about his career and what he wanted to do beyond basketball, using all of the friendships and relationships that he’s built over the years.”

Said Frye: “Richard is his own platform. It is amazing to see him evolve as a person, and ‘The Sports Gap’ is a great outlet for him to speak about relevant things — not just [about] X’s and O’s and numbers, and I love it for him.”

Mark W. Wright is a Charlotte-based sports journalist and documentarian.

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