While it might come as a surprise to many, former NBA vet and ESPN analyst JJ Redick is the first to admit that there was a time when he was actually quite introverted. It’s a chilly Wednesday afternoon in Red Hook, Brooklyn, and the “Old Man and Three” podcast host is on set at The Compound to film an episode for DraftKings’ Starting Five video series. Just moments earlier, Redick was hanging out with Set Free Richardson, Jadakiss, streetwear designer Don C, sports betting expert Danielle Alvari and NBA 2K insider Jamie “Dirk” Ruiz, reminiscing about his playing days at Duke, his relationship with Coach K, and the way the game has changed since he was in the NBA.
When we caught up with Redick after filming was done, he was just as reflective about his playing career and going into broadcasting and sports media.
“I think a big part of it was just going to play for the Clippers, to be honest with you,” Redick says of how he’s transitioned into media while being introverted. “Duke felt like a bubble. And then Orlando is a smaller market, even when we were really good it didn’t feel big. And when I went to the Clippers, big media market, a lot of eyeballs, we were a good team. The city’s huge. You start meeting people, you’re randomly at a fundraiser for the Democratic Party at Magic Johnson’s house and you’re up on stage with Harry Reid. And you’re like, what? How did I f***ing end up here? I’m taking a picture with Diane Keaton.
“By the time I was doing ESPN [and] by the time we had launched the ‘The Old Man and Three’ in 2020, I was very comfortable by then. I look at those four years in L.A. as sort of the growth and the journey. That, to me, was a pivotal moment in my life—and it coincided with me becoming a father. That gave me a whole new perspective on things and what mattered and not caring as much to be honest with you. Not being so sensitive.”
The decision to get into podcasting for Redick really started out of curiosity. “It was something other than basketball, which is something that I had thought about for a long time,” he says, later adding: “It’s weird, because I grew up so introverted and now I have to have gotten comfortable. I have to talk a lot on camera.”
It was around 2012-2013 when Redick, who was then playing on the Orlando Magic, took a trip to Boston to visit his best friend from high school. They hit up Fenway, as well as Harvard, where they ended up having a two-hour long conversation on the quad. “I remember thinking at the time, ‘I wish somebody had recorded that.’ I didn’t have the podcast [yet].” This moment ultimately contributed to the start of a journey that would lead to Redick diving into podcasting.
Now, Redick has established himself as one of the strongest voices within sports media, offering both a deep knowledge of the game, as well as a player-first perspective. Whether he’s challenging Stephen A. Smith on ESPN’s First Take, interviewing superstars around the NBA on the “The Old Man and Three” podcast, including Stephen Curry and Jayson Tatum, alongside co-host Tommy Alter, or going back and forth with the DraftKing’s Starting Five about the state of the game today, Redick admits that these are all skills—public speaking, asking questions, getting subjects to open up—that he’s had to learn and develop over time. Since he became the first active player to host a podcast when he launched a weekly show with Yahoo Sports in 2016, Redick has spent the past five years perfecting his craft with the same preparedness and attentiveness to the game as he did as a player.
“There are certainly comparisons, there are certainly similarities. I think a lot about preparation. For me, being undersized with a short wingspan, not particularly bouncy, not particularly agile—I mean relative to you, I’m a better athlete, but relative to NBA players, I was on the lower end of the spectrum. So I had to prepare and people tell me all the time, and it drives me f***ing crazy, ‘Oh, you’re a natural.’ And I’m like, ‘Mmm, no, I’m not.’ It goes back to the extroverted thing. I’m not. I’ve actually got hundreds and hundreds and hundreds and hundreds and hundreds and hundreds and hundreds of reps. Like last year, I would do a f***ing five-minute SportsCenter hit at 12 o’clock, I’m preparing 45 minutes for that. I get the questions. I’m doing my research. I’m thinking about clips. I do it the same way I played. That’s how I had to play and I look at it [like] I have to do it the same way here…Look, if we’re being honest, you go to Miami in Game 4, you’re down and you hit a big bucket down the stretch, you make the game-sealing free throws, and Joel gets the rebound to end the game and you’re going back in the locker room with your teammates to fly back to Philly to close them out. There’s no better feeling than that. We probably, as athletes, we probably won’t ever feel that again. There’s got to be some level of acceptance on that but you can still grind and search and challenge yourself in ways that you approximate that.”
When he’s watching the game these days, Redick pays keen attention to body language—a skill he learned at Duke while playing under Mike Krzyzewski.
“I think it’s because I played for Coach K, I am big on watching body language—and I know that sounds weird. There’s four or five actions you can run in the NBA, and there’s three or four ways to defend those actions, generally. There’s some creativity around watching Phoenix or Dallas—the different ways they get into the pick and roll. I find it fascinating and when I call their games, I’ve tried to find ways to point this out and break it down because I think most casual fans [are like], ‘Explain pick and roll. What’s that?’ [and] the Twitter nerds, they love it. But I watch body language a lot and when I’m evaluating a team, I’m watching the body language. When I’m evaluating a team winning or losing, I’m watching the body language. I’m watching players that have edge—I am fascinated by Jose Alvarado, T.J. McConnell, Marcus Smart. I love watching those guys.
“And then, as a true basketball fan, and this is where I, like, for whatever reason, run into such headwinds. I appreciate greatness. Shouldn’t we all? I guess not because so much of the narrative side of it is pointing out all the failures of great players versus celebrating the longevity, the scoring, the winning. It annoys the f**** out of me, to be honest with you. It does. I love watching Tatum play, I love watching Ja Morant. I view games through the analytical lens for sure, but I’m also just a basketball fan. I retired and I was like, I’m going to take a break, and then I had to sign up for ESPN, but then, like, f***ing two weeks into the season I’m like, Jesus, man, I’m doing the same thing I did as a player. I’m watching eight [NBA] League Pass games, switching back and forth channels, channels, channels, and then it’s 12:30 at night and I’m like, Okay, I can finally go to bed because I’ve watched all the games.”
For Redick, there’s “two components” to the way he approaches his work now as an analyst and podcast host: “There’s the analysis of the game, which to me, seems very black and white,” he explains. “In that, I can go look at advanced stats, and I can talk about them all day, I can watch a play, and I can break that down. It’s cut and dry. The narrative side of media, which is where I think I’ve made some headway, if that makes sense, that is the gray. Tobias [Harris] and I talk about this all the time, because he was such a black and white person, and it used to drive me crazy. I’d be like, ‘Dude, you gotta learn to live in the gray.’ And I like to live in the gray. That’s how I operate in my life. And so I think, every conversation we have about narrative, it’s always super nuanced. I enjoy having those conversations. That, to me, is where you get a lot of disagreement. And that’s inevitable, because so and so player, team, their stans. And you are never going to change the opinion of a stan. You’re just not. But I enjoy having those conversations. And I’m not always right. I know I’m not always right. And I knew when I was wrong. I do, or at least I try to. Kings fans, I’ve acknowledged that I’ve admitted the whole trade, whatever.”
Then there’s Redick’s ability to understand his subjects, an attribute that has made him so compelling as an analyst. He’s been there, not just on the court, but as a professional athlete who’s been put under a magnifying lens by the media and general public. When the scrutiny surrounding Russell Westbrook gets brought up mid-interview, Redick offers both perspectives—there’s the one that only he, and his former NBA teammates, could ever possibly understand, and then there’s the outside, fan perspective. “So, number one, we’ve all been memed and GIF-ed. I think we’re all cognizant that the camera is on us, but we’re also human. And I remember during the [NBA] bubble, our second game, we got blasted by the Clippers and I had to lay down because of my back, so I never sat on the bench. I’m rolling my back …and I’m, like, staring into the abyss. That became a GIF for, like, four days and it’s like, Yeah, you caught me in a bad moment. I was f***ing pissed. We were losing by 30 in the third quarter. Like, it happens. So, the body language part I get and certainly players like Russ are scrutinized, especially once different storylines get added in.”
It’s in the gray area where Redick shines most. By intertwining his knowledge of the game and 15 years of playing experience with his understanding of how NBA fandom works, as well as the media, Redick has been able to get players around the League to let their guard down and open up about never-before talked about topics, from mental health to getting cut from a team, in a way most broadcasters could only imagine. He’s still that same determined, competitive and straight-up clutch sharpshooter that he was at Duke and in the League—the only difference now is that he’s bringing that same passion to every assignment, every game and every interview.
“It’s the juice. Yeah, that’s the juice for me,” Redick says of getting players to open up. “When I played, the competition part was such a drug. And the highs of it were just so good. The lows were so bad. But it was so addicting, all of it was so addicting. And as athletes we really struggle to recapture that in our post-playing days, it’s damn near impossible. I sometimes get it on the golf course. Going back to recording, for the podcast, for me, that is the drug. When PJ Tucker talks about how, at the end of his first season, the Raptors cut him and prior to cutting him for the playoff run, they brought him into the office, the whole staff was there, and they showed we’ve had a camera on you. For the last two weeks, here’s your body language in huddles, here’s your body language when your teammates scores, here’s your body language in practice. Like, when he tells that story, that’s a high for me. When DeMar [DeRozan] opens up about his mental health approach and his struggles and his journey there, that’s a high for me. You don’t always get that in every interview or every episode, but when you get it, God, it’s so f***ing good.”
Watch the latest episode of the DraftKings Starting Five series featuring JJ Redick here.
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