Get access to everything we publish when you sign up for Outside+.
Jack Simes got his first real race bike—it was a chrome, fixed-gear Landini with 24-inch wheels and Continental tires—when he was only nine, perhaps too young to comprehend he was inheriting a rich family legacy yet old enough to appreciate the stories about trophies that had long sat in his grandfather’s garage. It was early in the 1950s and the sport of racing bikes was on life support in America, but as the boy watched his father train champions on cinder tracks he felt something beyond curiosity. “Back then every other kid was on a balloon-tire bike, bikes made by Schwinn that essentially were toys,” the racing legend, now 74, recalls. “But from the start, I was interested in speed.”
That Landini didn’t have brakes, so the fourth-grader learned how to stop his bike by gloving the wheel. He went out on hard, three-hour group rides with adult club riders. “My father taught me how to draft,” Simes says. “I was nine years old and I thought the proper way to ride a bike was an inch behind someone else’s wheel.” The boy started winning races—just as his father and grandfather had done. And just as his own son would do decades later.
With no offense to the accomplishments of the Phinney-Carpenter clan, if American bike racing has a first family its last name is Simes. “Our family goes back to the beginning of the sport,” says Simes. And it’s true—his grandfather, Jack Simes I, began racing bikes right before the end of the 19th century. He won the Boston 100-mile marathon race in 1904, and a year later got 27 stitches on his head in a crash on a banked track. “He talked very little about his racing,” says his grandson. “And all his trophies and medals were lost when his house burned down.”
But the old man had a fire for the sport and took his son, Jack Simes II, to watch big-time track races at New York Velodrome on 225th Street when it opened in 1922. That young man—our protagonist’s father—started racing with clubs in New Jersey in 1929. “He was fairly good from the start,” says Simes, which is kind of an understatement. When he was still in high school, Jack Simes II won a prominent 25-mile handicap race from Irvington to Milburn one morning, and another high-profile race that afternoon—netting the youngster a Chevrolet convertible, a Harley-Davidson motorcycle and national attention. (It’s true: Bike races had better payouts 80 years ago than they do today.) At one point, he had a win streak of at least 37 races, triumphing at distances ranging from 1 mile to 200 miles.
In 1936—at the age of 22—he won the national road race championship, held in St. Louis, and instantly became the favorite for an Olympic berth. But he suffered a late puncture at the trials and his dreams of going to the Berlin Games were dashed. “At that point in the sport the rules didn’t allow a bike change,” Simes recalls. Later that year his father would set U.S. records for 3 and 15 miles en route to winning a 30-mile race.
With the next Olympics seemingly far in the future, Jack Simes II decided to turn pro and sprint for fame and fortune on America’s track-racing circuit. He got his professional license in January 1937 and entered his first six-day race at San Francisco’s Dreamland Auditorium. It would turn out to be his last. “He got in a really bad crash,” Simes says, recounting an incident in which his father fell and smashed into a wooden railing. “He had internal injuries—serious intestinal damage. That was the end of his racing career.” Jack Simes II, possibly the fastest American bike racer of his day, had to retire at the age of 23. He kept riding recreationally (and played highly competitive ice hockey at Madison Square Garden), opened a bike shop and eventually started coaching other top cyclists.
Then came World War II—which changed the face of bike racing around the globe and permanently damaged the sport in America. In Europe, the bombing of so many major cities precipitated a shift from velodrome racing to the road. But in the United States, where other sports like baseball survived that period by promoting women’s leagues and then resuming professional play right after the war, the sport nearly died. “Cycling almost vanished after the war—it would have died if it hadn’t been kept alive by clubs,” says Simes, who was born in 1942. “Everything—the rides and the races—shifted onto quiet back roads.”
But while the sport was on the ropes and out of the public eye, a young Jack Simes III had a front-row seat to the subculture that remained. “My father was coaching Jack Heid,” says Simes, referencing a powerful sprinter who won bronze in the 1949 world amateur sprint championship. “I saw Heid race on cinder tracks. I was fascinated with how fast he could go.”
Simes grew up in New Jersey’s Bergen County in a town called Closter—now it’s a bedroom community in the New York City metro area but back then it was rural. Before he was 10 he was heading out with his father and other adult racers on long training rides that were the equivalent to the contemporary weekly world championships. “I was struck by the coolness of the bike, the freedom,” he says. “Even when I was nine and a half, I was amazed at how far I could go, all the different places I could go.”
He started winning junior races right away. But after a few years of constant success, Simes hit a major lull when he was about 12. “Other kids were growing and I didn’t understand it,” he says. The disappointment hit him hard. When he was 13, he got a school assignment to write an essay about what he wanted to be when he grew up. In his heart, Simes wanted to be the next Jack Heid, but he lacked the confidence to put it into words. “I couldn’t do it,” he says. “I wrote an essay that I wanted to be a dairy farmer.”
But milking cows was not Simes’ destiny. By the time he was 14 he was winning races again. “The real passion came out when I was 15,” he says. “And I won junior nationals on the track when I was 16.” Like his father, who had earned national attention in high school, Simes lit it up at an early age.
But he truly caught fire at the 1960 Olympic trials. Simes was still a teenager, ascendant and well regarded as a track racer but hardly a favorite. “I wasn’t even thinking about making the team,” he says. All of the nation’s best sprinters were there. But as the match sprint rounds kept coming, Simes kept winning. In his semifinal contest, he went up against one of the favorites, a guy from California named Ed Lynch who was riding an insane 128-inch gear. The races were held on a half-mile flat track in Flushing, New York, right next to where Shea Stadium would soon rise. Despite Lynch’s experience and huge gearing, Simes came off his wheel twice to advance. And the winner of the other semi-final was Herbie Francis, a local racer from Harlem who had defeated the legendary Jack Disney (who ultimately would race in four Olympics) and two other men in the last round—meaning that two unknowns, a high school student and the first African American cyclist to qualify for the Olympics, had punched tickets to Rome. Officials were so thrown off by the unexpected turn of events that they decided to skip a final match race.
The trip to Rome made a huge impression on the 17-year-old Simes. “That was my first time in an airplane,” he says. “And then suddenly I was living in the Olympic Village, essentially a small city with the best athletes in the world. It was an incredible experience.”
More than 50 years later, Simes still has vivid memories of Rome: the opening ceremony, the competition in the velodrome and watching TV in the dorms with amazed members of the U.S. track & field team as a barefoot Abebe Bikila win the marathon in world record time. But nothing compares to his brush with greatness in the Olympic cafeteria.
Simes describes walking through the enormous cafeteria, which was divided into different sections of food—Italian, Asian, and so on. “I walked into the American section and sat down next to this young black guy wearing a USA jacket,” Simes says. “He asked me what sport I did and I told him cycling. He asked why guys ride so slow on the track sometimes and I explained the strategy. I asked him what sport he did and he said, ‘I’m a boxer and I’m going to win the gold medal in a few days.’ He had no fear.”
Simes ran into the cocky 18-year-old—he said his name was Cassius Clay—the next day. “I saw him again and we started shooting the shit,” Simes says. “He had a bunch of thin steaks piled up on his plate like pancakes—he said he needed the meat for energy. He said, ‘When I win everybody is going to know my name.’” Simes ran into the future Muhammad Ali one more time in Rome a couple days later: Clay was walking around the village with a gold medal around his neck. And, as predicted, everyone knew his name.
Bike racing never brought Simes fame, but it did take him around the world and gave him an impressive collection of stars-and-stripes kits. Interestingly, when asked how many national titles he won or how many world championships he attended, he admits he’s not sure. “I think I went to worlds eight times,” he says with a less-than-certain tone. (Google later confirms his guess and offers a record of at least 12 national titles.) “But I know I went to the Olympics three times as a rider and one time as a coach.”
As the 1964 Olympics approached, Simes was no longer some below-the-radar prodigy. In a lengthy feature titled “Lure of the Wild White Noise,” Sports Illustrated profiled the 21-year-old racer in its Olympic preview issue, calling him “perhaps the best rider this country has ever produced.”
The story also included conversations with his father and grandfather. When asked to appraise his grandson, Jack Simes I, 79 at the time, offered a quick response: “Yessir. The kid is good.” His father was more circumspect. “If he doesn’t win a medal this Olympics, he could do it in four more years when he certainly will be stronger,” Jack Simes II told Sports Illustrated. “He could turn pro and make $50,000 to $60,000 a year racing. It’s big in Canada, and they’re trying to get it going again in this country. But I would rather see him get a good education and go into something else.”
Olympic glory eluded Simes in Tokyo, and again four years later—his best result was a 12th place in the 1-kilometer time trial in Mexico City—but he did earn a silver medal in that event at the 1968 track worlds in Montevideo. He also had plenty of success on the road, winning the Tour of Somerville in 1967, for instance. All these wins came as an amateur. Though it was essentially impossible to be a professional rider in the United States at this point, Simes was interested in turning pro and heading to Europe to ride in six-day races and other elite competitions.
There was just one problem: the Vietnam War. Simes recalls going to watch Muhammad Ali fight in Madison Square Garden—his last bout before the man formerly known as Cassius Clay had his boxing license stripped in every state because of his refusal to be inducted into military service.
Ali would not fight again for almost four years. “Ali was a giant,” says Simes. “He put his whole career on the line for what he believed.”
Simes didn’t want to go fight in Southeast Asia either. “There was a compulsory draft at the time and Vietnam was escalating,” he says. But top amateur bike racers of the day had one way to stay far from the front lines—to get a spot on the U.S. Army’s amateur bike team. “Bike racers knew that if you were good enough, you could get a bye out of shooting people.”
Simes spent two years in the service, starting late in 1967. He raced bikes and lived in California and had a job helping servicemen getting tickets to entertainment events. “I lived like a civilian and raced a lot,” Simes says. “I was planning to go pro and race in Europe. But here in America people told me that if I went pro I’d never be allowed to ride here again.”
But Simes would not be deterred. He got out of the service in December 1969 and, within days, he was on a flight to the Netherlands. He had a suitcase containing a few kits—no bike, no pro license, no commitments for an opportunity to race. Simes had written a Dutch promoter asking for assistance finding housing and ordered a track bike (from legendary Amsterdam builder RIH Sport). “For a few days I lived in this weird apartment in someone’s attic where the only cooking facility was a Bunsen burner,” Simes recalls.
Experienced racers recommended that he relocate to Antwerp. “So I got a BMW 700 and drove to Antwerp,” Simes says. He found a small apartment only 400 meters from the city’s famed Sport Palace. His next challenge was to get a pro racing license—without one he couldn’t race six-days in Europe. “I drove to Brussels to get a license from the UCI, but they wouldn’t give me one,” says Simes. Eventually, the Colorado-based U.S. Professional Racing Organization (USPRO)—an entity that is now part of USA Cycling—mailed him a license. Another hurdle was behind him.
Simes was just an unknown and inexperienced American hanging out in Antwerp, trying to make it as a pro. There were casual weekday races at the Sport Palace—on some days the owners didn’t even turn on the lights or the heat.
Then, on one weekday early in 1970, he got a big break. A lot of top racers were in town and the scene that Simes recalls is like something out of a dream. He walked into the velodrome and Eddy Merckx, who would go on to win the Giro d’Italia and Tour de France that year, was present. Rik Van Looy, who like Merckx had won all five monuments, was warming up. Jacques Anquetil—the first man to win five Tours—was there too. “It was his farewell tour at that point,” says Simes. “Anquetil was just lying there on the rub-down table”
The center of attention that afternoon was Rik Van Linden, the reigning Belgian national junior road champion, who was set to make his pro debut in a widely publicized derny race. But someone had backed out and race organizers needed another competitor. Simes was new to the discipline and was paired with a newbie derny driver, but it was a chance nonetheless. Simes says that someone set up his bike with a 55×14 gear and 30 seconds later the gun went off. “It was fucking brutal,” Simes laughs. “It was so hard that I was thinking of quitting halfway through. I felt like my kidneys were up in my throat.”
But Simes hung tough and unleashed his sprint at the end and wound up finishing second, only a length behind Van Linden. The next day an Antwerp newspaper referenced the performance in a bold-faced headline: “The New American—A Revelation.” The young American understood the game. “I knew it was just publicity bullshit,” he says. “But still, it gave me a break.”
That break came at the Antwerp Six-Day, held in mid-February. Simes teamed up with Great Britain’s Tony Gowland and Australia’s Graeme Gilmore. In the span of two months, he had gone from being an amateur in the U.S. Army to elbowing his way into the best six-day race in Europe.
The experience left quite an impression on the 25-year-old American. “Six-day races aren’t like now—they literally were six days and seven nights of nonstop racing,” Simes says. “You went into the building and didn’t come out for a week. I really didn’t realize what I was getting into. I saw [Olympic gold medalist and three-time track world champion Patrick] Sercu come in with his own bed. Meanwhile, I had a bunk made of stone with a straw mattress.”
Simes describes the seconds before racing began. “I was up on the wall, getting ready for the Madison to begin and there were 20,000 people cheering,” he recalls. “I just looked around and thought what the hell am I getting into?”
Thus began a barnstorming stint as a six-day racer, full of hard days against the hard men of that era. (Curiously, Simes says he doesn’t remember lining up against Merckx during his career, but the Cannibal has told me he remembers racing the American on the track.) Simes recalls one of the tougher days, racing a long Madison at an event called the Christmas Day Chase in Ghent. Early in the race, Simes’ team had slipped away and taken a lap on the field. “And before anyone realized what had happened, we took another lap,” Simes says. “And Sercu was there and suddenly he realized we had two laps on the field. The peloton just exploded—and we probably still had 500 laps to go at that point. Now that was hard.”
Simes ultimately partnered with fellow American John Vande Velde—an Olympian in 1968 and 1972 (who later did a cameo as one of the bad Italian guys in the film, “Breaking Away”) and father of future pro Christian Vande Velde—and the duo contested six-day events in Berlin and elsewhere in Europe. They notched a handful of podium finishes including a third against a stacked field of Euro talent at a six-day in Montréal held soon after the Munich Olympics.
With his elite racing career in its autumn years, Simes started running a bike shop in Nanuet, New York, in 1974. He was still racing, participating in an omnium series promoted by Shimano—the Japanese brand’s first big foray supporting bike racing in the States—but his interests were broadening. Simes was already coaching—he had guided the U.S. women’s team that hit the boards at the 1976 Games—and getting involved in race promotion, the national federation and other activities off the bike.
Then, in the summer of 1975, he read that Bob Rodale, the second-generation scion of the Rodale publishing business and a 1968 Olympian (in skeet shooting), had broken ground on a velodrome in rural Pennsylvania. “I got in touch and told Bob that I had some ideas about making it a business,” recalls Simes. When the Lehigh Valley Velodrome (soon best known as T-Town and in 2007 renamed as the Valley Preferred Cycling Center) opened, Simes was put in charge of running the enterprise along with former Olympian Dave Chauner. “Me and Dave had to go from zero to 60 in an area that knew nothing about track racing,” Simes says. “We had an organ and before long we had 4,000 people in the stands.”
After that stint managing the velodrome, Simes stepped away from cycling for the first time in his life. “I was ready to do something different,” he says. “I ran a restaurant and had a working horse farm.” Simes pauses in the conversation, contemplating a period in which he was disconnected from the sport that had defined so much of his life.
But a couple of young people restored his link to the sport. The first was his nephew, Ryan Oelkers. In 1985, Simes brought his 11-year-old nephew down to Philly to watch the inaugural USPRO Championship, won by Eric Heiden. The kid was transfixed and with Simes’ support he’d get into the sport. Oelkers would go on to race professionally. Along with Marty Nothstein, Oelkers won the Moscow Six in 2002, the only U.S. duo to win a professional six-day in more than 50 years.
And then, in November 1988, Jack Simes IV was born. “I think I truly came back to cycling when my kid started riding.” The kid—who his father and many others called Jackie—was on a bike early. “When he was little, I picked him up a bike with 18-inch wheels—the rear wheel had a fixed gear on one side and a freewheel on the other,” Simes recalls. “I’d ride with him to the bus stop, we’d do little sprints, I tried really hard to not be some little league father, to always make it fun. I know I enjoyed it—cycling gave me a chance to spend a lot of quality time with him.”
The elder Simes put Jackie in the PeeWee Pedalers program at the velodrome. So he was riding on the track at age nine, the same as his father. As his son progressed and got older, Simes watched Jackie and wondered if he’d stick with cycling. “At some point I could see how he would face a lot of peer pressure not to race,” Simes says. “Cycling isn’t a scholastic sport that has a strong social component for kids. Racing track bikes—that’s like you’re climbing mountains in foreign lands.”
Simes says that as an adolescent, his son was also into basketball. “I remember one day where I pointed out this really good player and explained how his sport might take him all over Pennsylvania if he was lucky,” Simes says. “And then I told him, ‘If you take cycling seriously, it can take you all around the world.’”
I lived in the area at that time and remember seeing Jackie out with his father at the local weekly training race—a spindly kid with junior gearing spinning like mad at the back of the peloton. “Coming up he worked really hard and he had a good work ethic,” Simes recalls. “I tried to show him the complexity of the sport—about man and machine, drafting, assessing competitors, gears. It’s like a Rubik’s Cube; there’s a lot to do. I told him to focus on doing work and having fun more than results when he was young. The world is full of dead-end junior champions.”
Over the span of a few years that felt like the blink of an eye in my middle-aged life, Jackie went from a skinny kid barely hanging on to a rock-solid young man smashing the break with pro riders. Jackie finished third in the under-23 points race at track nationals in 2008. The next year the one-time PeeWee Pedaler went pro with the Mountain Khakis squad.
Jack Simes IV had finesse and closing speed and found limited success on the road—riding for the Jamis-Sutter Home squad, he finished second behind Jesse Anthony in the 2011 Univest Grand Prix criterium—but showed his greatest promise on the track. He had multiple podiums at track nationals, excelling in scratch racing and the Madison.
It was in that latter event—a team discipline with roots back to the days that his great-grandfather took his grandfather to watch velodrome racing in New York—that Jackie really found his niche. The young man caught the eye of another fast local, Bobby Lea, and a very successful pairing was born. Lea, who Simes calls “one of the greatest endurance riders in this country, ever,” would wind up a two-time Olympian with 30 national titles. “Jackie and Bobby didn’t click right away,” Simes says. “But they kept working on it and they got so good.”
After finishing second in the Madison at nationals in 2011, the duo won stars-and-stripes in 2012…and 2013…and 2014. “It was a beautiful thing to watch,” says Simes. “You could tell they didn’t need to talk.”
Just as his father had done, Jackie headed to Europe to try his hand at six-day races. In the span of a few years, he lined up at 11 six-day events and finished eight of them. At the summer six-day held in Fiorenzuola, Italy, in 2011, Simes and Lea finished fifth overall against a quality field, beating overall victors Ella Viviani and Jacopo Guarnieri in the Madison. “I think they were the best Madison team in the U.S. in the past 75 years,” says Simes, a man who has probably witnessed the event more times than any American alive. “If the Madison had remained in the Olympics, they would have been medal contenders.”
Simes is referring to a change in the Olympic cycling program that was precipitated by the ascension of BMX to the Games and well-intentioned efforts to create gender equity in the sport. These positive steps came at a cost, and a number of endurance events in men’s track cycling—including the points race, 1-kilometer time trial and individual pursuit—fell off the program. And in the windup to the 2012 Games, the Madison was dropped too. “Suddenly Jackie had no event,” says Simes.
Jackie won three national track titles in 2013—with individual victories in the scratch and points races, and another Madison with Lea—but his interests were shifting. “In 2014 I could see a change—he didn’t say much about it, but I could tell,” says Simes. “Eventually he told me ‘I want to go back to school again.’ School was his thing.”
Jackie hasn’t raced since 2014. Simes says his son is almost done with his pre-med coursework and has taken his MCAT (Medical College Admission Test). And now, 53 years after his own father told Sports Illustrated that he would rather see his lightning-fast son “get a good education and go into something else,” Simes has a child who has walked away from bike racing and toward medical school. Simes is the farthest thing from disappointed. “Cycling was the thread that went through the family,” he says. “But academics—that’s his thing, his own identity. I support that.”
Simes hasn’t fully processed this turn of events, not out loud at least. It’s one thing to live your life—or even to examine how your father and grandfather’s lives shaped yours, and how it all might play out as your kid grows up—and it’s an entirely different thing to synopsize the 120-year arc of your family’s cycling life in a 90-minute phone conversation. But now, Jack Simes III is pondering the deeper meaning of it all: the hundreds of thousands of laps, the crashes, the medals and the disappointments, the lifetimes spent pedaling a bicycle through the woods and the cornfields. “This is something I never said to Jackie, but I suspect he figured it out on his own,” says Simes. “The thing you’re after in sport—above all, you want to look back and think it was a great time in your life.”
Simes says his son doesn’t hit the road a ton these days, mostly riding on the trainer to save time. But whenever son comes to visit father, the two head out for a ride into the Pennsylvania countryside, just like the old days. “We just went for a ride a week ago,” says Simes, recounting a mid-August loop the two shared. “I’ve been riding a lot this summer so I’m going okay. We went out and rode a really nice tempo.”
Simes pauses briefly, remembering the ride. “It was great, we were side by side just like we did when he was young,” he says. “I tried to muscle him into a puddle but he wasn’t having it.”