Reggie Miller says he has arranged perfect riding weather for us. It’s a joke, of course. This is Malibu. It’s always a beautiful day. It’s the first of December, and 73 degrees. The sun bathes us in dry, uncomplicated warmth. A light ocean breeze promises to cool us on the climb.

Still, it’s not hard to imagine Reggie Miller having some direct line to a higher power that he could occasionally call on. He is, after all, Reggie Miller—one of the NBA’s all-time best long-range shooters, who had the league’s record in career three-pointers when he retired. Reggie Miller, the former Indiana Pacer who once scored eight points in 8.9 seconds to crush the New York Knicks’ 1995 championship dreams in Madison Square Garden. A colleague of mine who was at the game recalls the stunned silence that followed: “And then the wailing began.”

The Knick Killer is no longer in the business of making strangers cry. These days—13 years since he retired and six years since his Hall of Fame induction—Reggie, now 52, can be found hamming it up on TNT as one of the cable network’s NBA analysts or playing with his son and daughter, ages 4 and 2. The rest of the time, as one Reddit commenter puts it, “Reggie Miller eats, breathes, and shits bikes.”

Go to his Instagram feed, and you’ll see that every other post is about riding: a GoPro video of a techy descent he just conquered; a photo of him grinding up a dusty Southern California fire road, #EmbraceTheBurn. He even races and has a coach—pro mountain bike racer and 24-hour world champion, Sonya Looney.

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When I learned of Reggie’s passion for mountain biking, I was intrigued. It’s not surprising for a pro athlete to seek another competitive outlet after retirement. But how did he find and fall in love with the fringe sport of mountain biking? Even more interesting, he didn’t appear to be blowing people out of the water immediately with his superathlete talents—he had only recently won his first local XC race, in the Beginner class. Still, he was clearly all in. What did an Olympic gold medalist hope to gain from becoming an amateur mountain bike racer?

There was only one way to find out, really. I asked Reggie to go for a ride.

As we kit up in the parking lot at Point Mugu State Park on this made-to-order morning, I think cycling is clearly treating Reggie well. His 6-foot-7 frame is still trim. His caramel skin is marble-smooth. He’s aged so gracefully, he doesn’t so much look like an older version of himself, as he makes the Reggie Miller I remember from my youth—when my parents, sister, and I spent so many evenings curled up on the couch watching NBA games—look like a kid by comparison.

Reggie, who identifies as a classic fastidious Virgo, had arrived 15 minutes early. His size XXL Santa Cruz Tallboy, the only production full-suspension bike he’s tried that fits him, is meticulously clean. His yellow and blue “BoomBaby” jersey—a collaboration with Castelli to raise money for the Dropping Dimes Foundation, which helps American Basketball Association players who have fallen on hard times—matches his bike and his yellow argyle socks. When you look good, Reggie tells me, you ride good.

Strava shows that he routinely posts 4-plus hour rides, so I’m secretly relieved to learn that we’ll do one of his favorite shorter routes: Guadalasca to Backbone, a 13.5-mile loop that rises 1,500 feet into the Santa Monica Mountains and features ocean views. As we start up the well-maintained fire road that leads to Guadalasca, he calls out an enthusiastic “Good morning!” to everyone we pass.

Reggie’s first ride was in 2002, when Rage Against the Machine bassist Tim Commerford recognized him at a restaurant and invited him to come along on a ride that included renowned big-wave surfer, Laird Hamilton. On a heavy bike borrowed from Commerford, not clipped in, Reggie found himself huffing and puffing to keep up. And he was impressed by his companions’ athleticism. “To see [Laird and Tim] get after it,” he recalls, “I was like, ‘Yeah, this is what I want to do.’”

He bought himself a Giant with 26-inch wheels immediately after, but he was still playing for the Pacers. To injure himself could be a breach of contract, so he rode only occasionally until he retired in 2005.

At that point, Reggie turned to cycling as a way to stay in shape—he wanted to look good in his suits for TNT. Then he started going on longer rides, exploring the rugged canyons near his home in Malibu, and fell in love with getting way out there, to the middle of nowhere. The adventures got bigger. A few times, he even left a car for himself at the beach, arranged a ride home, and rode over the mountains from his house to the ocean.

He started exploring the rugged canyons near Malibu, and fell in love with getting way out there.

But the real game changer happened about two years ago when George Mota, a local racer, reached out to Reggie via Instagram and invited him to be his partner for a six-hour endurance relay. “I didn’t want to finish last,” Reggie recalls. “I didn’t want it to be like, ‘Oh God you had Reggie.’”

To his relief, the duo finished mid-pack—and he found himself hooked. Now he competes in individual cross-country and endurance events. This past season, he won two races in the Beginner 50+ category, so for 2018 he’s upgraded to Sport, the mid-tier level of amateur racing. He’s worried, he tells me. “The 50+ guys are really fast. I have to do a lot of work.” (It seems he needn’t have stressed too much—at press time, Reggie was already racking up mid-pack finishes in his new field, and most recently a fourth-place result.)

Already, within these first 30 minutes on the trail, I’m struck by Reggie’s seeming lack of ego on the bike. Earlier, in passing, I had called him a “very good” rider, and he had quickly corrected me: “I’m okay—I’m trying to get better.” It’s hard to imagine that this affable, self-effacing guy is not only a world-class athlete, but also was one of the NBA’s most notorious trash talkers, who owns the dubious distinction of having (on separate occasions) provoked both Michael Jordan and Kobe Bryant into fist fights.

“I’m a little bit more forgiving and humble on the bike,” Reggie acknowledges. “Maybe it’s because I’m still new to it, but trail etiquette is a lot different than basketball court etiquette. Growing up playing on the streets, you made your name by talking mess and getting into people’s heads. Out here, especially in the races that I’ve done, I see myself lending a hand a lot more. Everybody’s lending a hand to me.”

He feels gratitude to certain members of the community in particular. His relationship with Looney, who is based in Kelowna, British Columbia, began when Reggie started asking her questions about training and equipment via Instagram. He’s also logged miles with pro riders like Red Bull Rampage winner Kyle Strait and his wife, Rachel, and pro enduro racer Lauren Gregg. Reggie sees them as mentors, similar to the ones he had in his NBA rookie days. “They’re teaching me ’cause I really don’t have a clue. I’m learning on the fly.”

Looney, who communicates with Reggie nearly every day by text or phone, explains, “When Reggie says he’s an ‘okay’ rider, he’s comparing himself to the best person in the sport, because that’s how Reggie is. When he started riding with pros, he saw how far he had to go. He knows how hard you have to work for that.”

And even by pro athlete standards, Reggie Miller is very good at hard work.

Michael Darter

Reggie started watching basketball as a kid, through his kitchen window.

The games were between his two big brothers, Darrell and Saul, and his older sister, Cheryl. Little, chubby Reggie—whose ears stuck out—wanted desperately to play too. But he couldn’t. His legs were shackled in steel braces.

He had been born with deformed hips and splayed feet. As Reggie recounts in his memoir, I Love Being the Enemy, a doctor had looked at his twisted legs and said he might never walk. So while his siblings played, Reggie “lurched around” in those braces, and hung out with his mom, Carrie, in the kitchen of their Riverside, California, home. But his mom reassured him. “Don’t worry, honey. You’ll be out there soon.”

She was right. Reggie got the braces off when he was 5 years old and jumped straight into those backyard games. Cheryl, who was taller than he was and fiercely competitive, had never taken pity on her little brother, and now she took no mercy. “Remember that game, Rock ’Em Sock ’Em Robots?” says Reggie. “I was her human Rock ’Em Sock ’Em Robot.” Reggie learned his trash-talking skills in the backyard. It was one of his few weapons against his bigger, more skilled siblings.

“He would just talk—nonstop talk,” Cheryl says in the documentary Winning Time: Reggie Miller vs. the New York Knicks. “He would never shut up.”

The Millers were a special family. Darrell went on to play baseball for the California Angels. In high school, Cheryl became an All-American basketball player who once scored 105 points in a single game. Her career points record—3,018—at the University of Southern California still stands, and her jersey is retired there. She went on to help the US women’s team win its first Olympic gold medal in 1984, and to beat Reggie to the Basketball Hall of Fame (she is also in the Women’s Basketball Hall of Fame).

Reggie was in awe of his sister, but he hated always losing to her, always being introduced as “Cheryl’s brother.” On top of that, he didn’t hit his growth spurt until his sophomore year. His high school coach hadn’t wanted to start him until the day one of the regular starters forgot his jersey at home.

Miller celebrates a three-point shot that sent a 2002 game against the New Jersey Nets into overtime. MATT CAMPBELL/AFP/Getty Images

Reggie practiced like hell to prove himself. He’d take 500 shots a day in the backyard, working on his long-range shot because Cheryl always blocked him when he drove. He simulated high-pressure plays, throwing himself the ball for hours: Three, two, one; game’s on the line. To him, it was a simple calculation: If he had a 50-50 chance of making it and being the hero, more practice would make it 60-40. More gym work would make it 70-30.

Even as he moved up the ranks, Reggie was never physically the strongest, the most hyped, or (in his view) the most gifted. He says he got recruited to UCLA only after the school’s preferred players went elsewhere. Pacers fans booed when he was drafted to the team (they wanted home-state hero Steve Alford). So Reggie honed a strong mental game, became an analytical player. He studied videos of his opponents, memorizing their habits, learning their insecurities.

These experiences shaped him as an athlete. Reggie believes he made it to the Hall of Fame because of his hard work and determination, not because he was the most talented.

It’s natural for him, to not be the natural.

Reggie has a nemesis on this ride. As we pick our way up a steeper, more eroded 4x4 track, he points toward the shrubby ridge where we’re headed. A near-vertical trail called Hell Hill cuts straight up the fall line to the top of that climb. Reggie’s never made it all the way up, but when Looney came to visit last fall, she proved it’s rideable. “That’s my goal,” Reggie says. “When I can do that, I’m ready for anything.”

I’m okay with skipping this test of character today. Instead, we turn left up Guadalasca, the more gradual singletrack ascent.

Looney prescribes Reggie a plan, including interval and skills work, for the four days a week that he rides during basketball season (he travels the other three days for games). She says he does everything she says, exactly as she assigns it. He also does strength work in the gym, something he started after a bad crash last year left him with a fractured scapula and black eye, taking him off the bike all summer.

“Actually, the crash was the best thing that happened,” he says, ever analytical. “I was taking shortcuts. I had to get in the weight room.” He says that his height, which was such an asset on the court, makes it more difficult to get into the low position for confident descending. So he works with a trainer two days a week to improve his core strength and overall balance. He’s also learning more about equipment and bike setup, tire pressure, and suspension settings.

“Being back on the bike and starting this all new again brings back memories of the grind,” he says. “Pee Wee basketball, high school basketball, waking up at six or seven in the morning to go to the gym and work on my game.” It’s a feeling he likes but had lost touch with as a pro. “It’s the best,” he says. “The whole Drake song, ‘started from the bottom, now we’re here.’ I like it.”

“Mountain biking is such a very small community,” he continues. “I just want to put the hard work in so people don’t think I’m a slacker. I want the hardcore mountain bikers to respect, ‘Okay, well he did it the right way.’”

When Reggie says he's an 'okay' rider, he's comparing himself to the best person in the sport.

Descending is Reggie’s biggest challenge. He’s cautious, and sometimes that frustrates him. He admires the easy style of great enduro and downhill riders. “I want to kick up dirt, be a shredder, do all that,” he says. But Reggie knows that means learning technique and taking some risks. “You have to practice. And if you practice, you’re going to crash,” he says. While Reggie sees crashing as a badge of honor, he doesn’t know if he’s willing to crash over and over. Commentating is his job, it takes priority, and having to go on TV every week, he can’t injure himself or mar his face. Plus: “Bones don’t heal like they did when you were 22,” he says. “If I was younger without two kids, probably, but I don’t know if I have time to really learn.”

At the top of the climb we pull over to enjoy the panoramic views of the chiseled mountains. Two white-haired gentlemen ride by on identical carbon, full-suspension Treks. Reggie says “great job” to both of them, then turns to me, energized, once they’re out of earshot. “See, Gloria, this is what I love about mountain biking. Doesn’t matter how old you are. These guys are out here shredding it.”

I ask him if it ever struck him that cycling is such a white sport. “There should be more brothers on bikes, more brothers in races,” he says. “As kids we all wanted a bike. But a lot of people don’t have that opportunity, especially in the inner city. Hopefully, when people see me riding bikes and trying to do this at 52, they’ll see that there are other avenues besides baseball, football, basketball. I wish I would have been doing this when I was younger.”

Reggie’s family wasn’t poor when he was growing up, but money was tight. More important, he simply wasn’t exposed to mountain biking. So Reggie’s son has a bike, which he loves. But he also plays basketball, and soccer, and does karate, gymnastics, and swimming. It makes Reggie happy that his son is having the experiences he wishes he’d had as a kid.

He hasn’t been as successful getting his NBA pals on the trail. “I’d love to see big Shaq out here. Love to see Charles [Barkley],” he says. “They think I’m crazy. They’re like, ‘Retired means retired. It’s not doing all that working out.’” He gets a little louder. “I’m like, ‘No, retired means still being fit, looking good.’ When you retire, you don’t get fat and old. C’mon, it’s like a shark. Sharks never stop swimming, that’s when they die. You gotta keep moving.”

Descending Backbone Trail outside of Malibu. Michael Darter

Reggie played 18 years for the Pacers, and helped lead them to 15 playoffs. But he never won a championship.

The closest he ever got was in 1998, when they battled Michael Jordan’s Chicago Bulls to Game 7 in the Eastern Conference Finals. Reggie can point to so many plays that he wishes had gone differently, but one stands out.

With just over six minutes left in the game, the Pacers lead 77-74. There’s a jump ball—Jordan versus Pacers center Rik Smits. Smits loses the tip. Out of the ensuing scrum, Bulls forward Scottie Pippen gets the ball, slings it across the key to teammate Steve Kerr. Kerr sinks the three. Tie game. From that point on, as Reggie tells it, the Pacers lose their momentum.

Reggie thinks about that game to this day. He thinks more about the losses than the wins. They came so close to that trophy for so many years.

Getty Images

Most of us remember the high points. We think of Reggie as the clutch player who shined brightest when the pressure was turned all the way up. Like the 1994 play-off game when he scored 25 points in a single quarter against the Knicks. In the YouTube video, he shoots wildly from every angle, the ball firing from his fingertips like an electrical impulse, his legs still churning as it swooshes through the net. In those moments, Reggie says, he felt like he left his body. Everyone else was moving in slow motion. He was going 100 miles per hour.

Reggie has yet to experience that on a bicycle. But he’s patient. “It’s coming,” he says. Until then, he stays in his body, rides within his limits. Before we start the descent, he warns me about the views. “You’re gonna be caught wanting to look around, but if you fall, you’re going over.” The first portion of Backbone drops quickly from the ridge top into a bench-cut trail that swoops and turns like a roller coaster, popping us out of each banked turn like a pinball. Reggie stays low in the berms, but slips around corners with the fluidity of someone intimately familiar with the trail. He catches a little air over a bony rock cropping.

The sensation of buttery speed makes me smile all the way down, and by the bottom my teeth are coated in a fine film of dust. We pump through a small trough and skid to a stop on the fire road, bursting with adrenaline. “How cool is that?” he whoops, and we high-five. I feel a little wistful that the ride is coming to an end. It’s fun riding with Reggie. As we pedal back to the trailhead, I ask him about Game 7 against the Chicago Bulls. Has he made peace with it?

“I don’t know if you ever really make peace with [those moments],” he says. “Wouldn’t we all like to have do-overs in our life, in anything, in relationships and schooling and any type of adventure? But that’s what life is about, it’s about moving forward and learning from those mistakes, and getting better.”

With bike racing, Reggie’s not out to win the championship he never did in the NBA. “I’m too old for that,” he says. “I just want to have fun. The best thing that has happened has been the racing. It brings back those juices, you know, your name being called in the starting lineup, and you’re competing. It’s a different discipline, but still those juices are there.”

Early one morning, a couple of months since my ride with Reggie, I’m scrolling through my Instagram feed when I see that he has posted a new GoPro video, a POV of him attempting a steep climb. I recognize that sun-baked fall-line trail immediately: Hell Hill.



He starts impossibly fast for such a stout grade, like only a superathlete could. The GoPro lends a hollow quality to all the background noise: his suspension knocking, his tires scrabbling on dirt. The climb gets steeper, but Reggie powers ahead.

It really kicks up now. The footage bobs as Reggie slows a bit, but he continues to lay down steady pedal strokes. He starts to cut right, across the trail. You can almost see the top, can almost feel it as he strains to turn over the cranks once, then twice more. Reggie is so committed, he doesn’t even put a foot down. His yellow bike flashes into the frame as he tips over, still clipped in, into the brush.

The video stops here, but I know what happens next. Reggie Miller gets up, dusts himself off, and keeps riding.

He’ll get it. It’s only a matter of time.

Editor's Note: Reggie conquered Hell Hill on March 26, a few days before this story hit newsstands in the May 2018 issue of BICYCLING.