Searching for “X” From issue 31 • Words by John Wilcockson w/images from Horton Collection

“X” was the greatest classics rider of all time. But who was “X”? Perhaps that’s an impossible question to answer because over the 120 years that cycling’s major one-day races have been held, the athletes, the technology and the events have been constantly changing. If we go by results alone, there is only one answer: Eddy Merckx. The legendary Belgian won 27 times in the nine races that were regarded as the top classics during his racing era, the late-1960s to mid-1970s. Merckx missed out on only one of those nine, Paris-Tours, whereas his predecessor, Rik Van Looy, won all nine classics for a total of 16 victories. So was Van Looy a better classics rider than his fellow Belgian? And what about those who raced before them, including the Italian legends Gino Bartali and Fausto Coppi? And should we consider current standouts such as Tom Boonen, Fabian Cancellara and Philippe Gilbert? Let the debate begin….

It takes a variety of skills and abilities to win one of the nine major classics, today or a century ago. The early classics demanded greater qualities of endurance rather than speed because they were often battles for survival, ridden on heavy, single-gear bikes over dirt roads that would be mud tracks in the wet or dustbowls in the dry. Today, despite the advances in technology, a classics winner still has to have the stamina to be fast and strong after six or seven hours in the saddle.

Because of the restricted nature of the fields before 1946 (see “The Nine Classics”), very few riders from that era can be considered in our quest to find “X.” However, a few names should be put in the mix, including Frenchman Octave Lapize, who was the first rider to win three consecutive editions of Paris-Roubaix (he did the same at Paris-Brussels, and he also won a Paris-Tours); and the Italians Costante Girardengo (six wins at San Remo and three in Lombardy) and Alfredo Binda (one win at San Remo, four in Lombardy, along with three world road titles). Strictly speaking, the world road championship (inaugurated in 1927) is not a classic because it is held in a different country every year; but it is the only single-day race that consistently sees the world’s best riders on the same start line. So, because of its undoubted status, I’ve included worlds as a potential tiebreaker.

So who were the best classics racers ever?

Often the difference between winning and losing can depend on a split-second decision: Which breakaway should I go with? When should I attack? Should I wait for the final sprint? Those decisions, today, are often shared with a rider’s directeur sportif in a two-way radio conversation; but the best classics riders know almost by instinct when to make a move. And interestingly the careers of virtually all of the sport’s greatest one-day racers happened before wireless technology came to the peloton.

The very best classics competitors are those who, at key moments, can gauge their own strength—and that of their rivals. That might mean knowing exactly when they can ride others off their wheel with a sustained turn of speed (like Cancellara did at the 2010 Paris-Roubaix, making his move prior to a section of cobblestones when main rival Boonen was at the end of the line of riders), or with a sudden acceleration on a steep hill (like Gilbert did at the 2010 Giro di Lombardia to dispose of Michele Scarponi at the top of the final climb). They also need to be able to “read” a race, to be ready to make that split-second decision that allows them to get a shot at the victory. That includes the group of riders who may not have the natural ability to make a 50-kilometer-long solo breakaway like Boonen or Cancellara, but they have the smarts to jump into the right break, conserve their energy and keep enough strength to out-sprint “superior” riders at the end. Think Simon Gerrans, who did all those things to win the 2012 Milan-San Remo ahead of Cancellara, Vincenzo Nibali and Peter Sagan.

I’ve been lucky enough to watch, interview and write about some of the greatest classics riders over the past five decades; and I learned about the ones I didn’t see, including Coppi and Van Looy, from more senior colleagues who were reporting races in the 1940s and ’50s. After taking into account all those anecdotal stories, seeing all the classics many times, and learning exactly how certain races were won or lost, I’ve come up with five names of riders who are arguably the very best classics riders of all time. I’ll discuss them in chronological order, and at the end of this piece I’ll report a make-believe race in which the five, and their teams, compete against each other—and see who comes out on top.

Fausto Coppi

Like Girardengo and Binda before them, Bartali and Coppi began their careers by racing almost exclusively in Italy. The Bartali-Coppi rivalry began at the Giro d’Italia in 1940 when Coppi, at age 20, was selected to ride for Bartali’s Legnano team, and Coppi usurped his leader and won the race. By that point, Bartali, then 27, had already won Milan-San Remo twice, and did the same at the Tour of Lombardy. But then came a world war….

Before the hostilities reached Italy, Coppi showed his potential as a classics rider by winning four domestic classics in 1942 (the Tours of Tuscany, Veneto and Emilia, and the Tre Valli Varesine). He then went to North Africa with the Italian army and was taken by the British as a prisoner of war. Because of the lost years, Coppi’s cycling career didn’t really take off until 1946 when he joined the Bianchi team. That season opened with Milan-San Remo. Bartali was the big favorite, and he laughed at Coppi’s decision to chase after a breakaway in the first hour of the eight-hour race. But the younger man didn’t falter. He dropped all his companions up the mid-race Passo di Turchino and raced the final 140 kilometers alone to beat the runner-up, French star Lucien Teisseire, by 14 minutes; Bartali, humiliated, came in fourth 18 minutes back. Coppi had won his first international classic.

Perhaps Coppi’s greatest season was 1949, when he became the first man to win both the Giro and Tour in the same year. That season, which ended with him winning the Tour of Lombardy for the fourth year in succession, began as usual at Milan-San Remo. It’s a race that showcased Coppi’s greatest skills as a classics rider….

One of the first continental journalists I met was U.S.-born French journalist René de Latour, who wrote for L’Équipe in Paris and was a regular contributor to the UK magazine Sporting Cyclist, which I also wrote for in the mid-1960s. De Latour and Coppi were friends, and the French scribe said the 1949 San Remo was “a race I shall never forget.”

Back then, before the Cipressa and Poggio climbs were added to the course, the last hill was the Capo Berta out of Imperia, some 30 kilometers from the finish. That climb is just 3 kilometers long and less than a 5-percent grade, but it offered Coppi his last chance to attack the leading group of 12 riders. Watching from a press car, de Latour remembered, “Twelve men together. Good for them, bad for Fausto. Last year at the same spot he had been away on his own, and won by five minutes. Was he going to be an also-ran in this year’s sprint?

“How it happened is still clear in my mind. Coppi was working away at the front and working to a purpose, five having already sat up beaten. Another two bends of the hill remained. Only three on his wheel now, and they were straining like grim death to hang on, even though Fausto had only one hand on the ’bars and was searching with the other in his feed bag for a banana. On the top of the Capo he was alone with a 20-meter lead.

“Then the real work began, for it is one thing to drop a few men on a climb. To keep away from half a dozen working together on the remaining 27 kilometers of descent and flat is a different matter. The valve fully opened, Coppi steamed off toward San Remo, the unstoppable express…while the men behind, despite an organized chase, came in more than four minutes after Fausto finished.”

De Latour said it was a rare thing for Coppi to win a sprint, and most of his 10 classics victories (a Paris-Roubaix and a Flèche Wallonne, along with his three at San Remo and five in Lombardy) were solo efforts. “And think what his record would be,” de Latour said, “had he not had so many accidents, including a broken leg, and lost five years to the war.”

Rik Van Looy

The 1950s and ’60s were a golden era for pro cycling with stars such as Bartali, Bobet, Coppi, De Bruyne, Kubler, Magni, Ockers and Van Steenbergen doing battle in the classics. It was also the period when Belgium’s Rik Van Looy became the first (and still only) man to win all nine of the top one-day races. Even though he was a stocky rider with massive thighs, he was able to get over all the hills, even at the Tour of Lombardy, and remain competitive in a final sprint. And though his great finishing speed helped him earn multiple victories at Roubaix, Flanders, Wevelgem, Brussels and Tours (and three world titles), he also had the power to take solo wins.

In fact, three of his best-ever victories came in quick succession at the cobbled classics of 1962 when he was wearing the rainbow jersey as the defending world champion—and he didn’t need his sprint to win any of them. This is what I wrote about that streak in peloton issue number 12:

In Ghent-Wevelgem, Van Looy…instigated a break on the Kemmelberg with four others, and dropped them 5 kilometers from the line to win solo. At the Ronde van Vlaanderen, he responded to an attack by Tom Simpson on the Kwaremont, four others joined them, and in the final loop Van Looy jumped clear to win solo again. Then at Paris-Roubaix, Van Looy made constant accelerations until only five were left with him after the last section of cobblestones—and he simply rode away from them with 3 kilometers left. Van Looy’s winning performance was so impressive that race organizer and L’Équipe editor Jacques Goddet wrote: “He’s the greatest racer in the greatest race…a shining cyclist who is as firm and cold as marble and remarkably cool and lucid.”

Eddy Merckx


The world knew that Eddy Merckx was an incredible talent when he won the world amateur road race title at age 18—the youngest ever. But, after wearing his rainbow jersey to win four of five early-season amateur races in 1965, he had a shock in his very first pro race, the Flèche Wallonne. Merckx ran out of steam chasing the peloton after a flat tire and abandoned the race—and he wasn’t pleased with the lack of support from his Belgian team, Solo. He also resented being on a team with Van Looy, a man he never got on with. Merckx didn’t start another classic that rookie season and signed with French squad Peugeot for 1966.

Merckx promptly finished fourth in the weeklong Paris-Nice before his first-ever race in Italy, and his first monument, Milan-San Remo. Despite his concerns about the 288-kilometer distance, he bridged from the peloton to the lead group just before the Poggio and readied himself for the finale. “I started the sprint from a long way out,” Merckx said, “and to my utter amazement no one got past me.”

It was a dream start to the 19-year-old Belgian’s season, but he made all sorts of rookie mistakes in the rest of that year’s classics: he crashed out of Flanders; he couldn’t recover from chain problems at Roubaix; he exhausted himself at Liège before five-time Tour champ Anquetil made the winning break; and he was outmaneuvered at the Lombardy finish by Salvarani teammates Felice Gimondi and Vittorio Adorni. Merckx admitted that losing so many races helped him improve. Also, in his first three seasons, his pre-season preparation was based on indoor track racing, including six-days, and he didn’t attend a first road training camp until he joined the Faema team in 1968.

Today, most cycling fans associate Merckx’s career with the Grand Tours he won (five Tours, five Giri and one Vuelta), but even before he made his Tour debut in 1969 he had won nine times at the major classics. The best of those early victories came at the 1969 Flanders. It was a win that displayed many of his strengths—including the powerful teammates who gave him the solid base from which he constructed his best performances.

In that ’69 Flanders, Merckx made the most use of the cold, windy (and later rainy) conditions, his growing confidence, and his inner drive. On reading the morning’s newspaper headlines that he didn’t have what it took to win Belgium’s top classic, Merckx remarked, “We shall see.” After just 100 kilometers (with 159 kilometers still to race), he surprised many of the favorites, including Van Looy, by jumping after two riders who went for a town sprint prize. This was just before the race changed direction and Merckx’s effort saw two-dozen men ride clear, now with the wind at their backs. After the first cobbled climb, the Kwaremont, where Merckx forced the pace with British rider Barry Hoban, the front echelon split in two, leaving a dozen leaders heading into the final two hours.

There were two main clans: four Italians and four Faema team riders (including Merckx). Everyone was working together, believing that the race would be settled in the final hour or even in a sprint. But then, on a small uphill with more than 70 kilometers left, Merckx made his pull into the wind and eased to the side, expecting the next rider in line to take over. But no one came. Most people would have waited, but seeing a gap Merckx kept pedaling strongly, but not too hard.

By the time he was a minute clear, with the rain now pouring down and the Flemish crowds cheering on their new hero, the Faema team car was allowed to pull up to the lone leader. According to contemporary accounts, Merckx asked his directeur sportif Guillaume “Lomme” Driessens if he should continue with his effort, and the Belgian boss told him to carry on. Merckx, however, a few years later, said: “Driessens came driving alongside me and asked me if I’d gone completely mad. I can still see it now, [the passengers] sitting in the car with Driessens. ‘Go screw yourself’ is what I screamed back in Lomme’s face. And I carried on and won.” The next rider to finish, Gimondi, was almost six minutes back.

That Tour of Flanders showcased Merckx’s brilliant tactical mind: accelerating to ditch opponents in the early crosswinds; keeping up the pressure on the cobbled climbs to see off the weaker elements in the break; and knowing the solo-riding capabilities he developed in long hours of hard training. But it was that hidden fire he showed in cussing out Driessens that drove Merckx to wanting to win every race he started.

That drive was encapsulated in a story Hoban once told me. The Englishman was in another 12-man breakaway group in the finale of the 1974 Ghent-Wevelgem—a race Merckx was keen to win after six weeks without a major victory. For the final sprint, Hoban was in the mix with three of the most successful Belgian classics riders, Merckx, Eric Leman and Roger De Vlaeminck. “The sprint was going full out,” Hoban said. “Then, in what seemed a miraculous way, the three Belgians fanned out…and a gap opened up between Merckx and Leman. I shot through the gap…and passed the checkered flag one bike length ahead of Merckx. I was absolutely overwhelmed to win by first-ever super-classic…. In contrast, Eddy Merckx was like a spoilt child having had his favorite toy stolen, telling the TV and radio commentators, ‘I didn’t even know Hoban was there’ and ‘What can you expect, my wheel’s the best wheel to follow…’”

Roger de Vlaeminck

Two years younger than Merckx, Roger De Vlaeminck burst onto the scene in 1969 (the year Merckx won his first Tour de France) by winning his very first pro race, the semi-classic Omloop Het Volk (known today as the Omloop Het Nieuwsblad). De Vlaeminck also won the Belgian national championship that same rookie season. Those early successes made him a marked man in all the classics, but that didn’t stop him becoming only the third rider (after Van Looy and Merckx) to win all five monuments.

De Vlaeminck’s father was a huge cycling fan, and this influenced his two sons, Erik (who went on to become world cyclocross champion a record seven times) and Roger (who also won ’cross worlds in the amateur and pro categories). Their dad’s favorite racer was Rik Van Looy—who became Roger De Vlaeminck’s boyhood hero. “I had a true admiration for Van Looy,” De Vlaeminck once said. “That’s one reason why I always tried to stop Merckx winning Paris-Tours. I even sacrificed my own chances of winning to make sure he didn’t win.”

De Vlaeminck’s longtime rivalry with Merckx began in 1970. After Merckx dominated that year’s Paris-Roubaix, finishing more than five minutes ahead of his fellow Belgian, De Vlaeminck turned the tables at Liège-Bastogne-Liège. The two were in the six-man break that arrived at the finish on Liège’s Rocourt Velodrome, along with De Vlaeminck’s brother Erik—who blocked Merckx from chasing Roger when he jumped ahead entering the track.

Their rivalry was at its height on the cobblestones of Roubaix, a classic that De Vlaeminck won a record four times to Merckx’s three. He became known as Mr. Paris-Roubaix (he also placed second four times), but De Vlaeminck had all-around talent that allowed him to win six consecutive editions of Italy’s Tirreno-Adriatico stage race and beat Merckx in a Tour of Switzerland. They both won Lombardy twice, and De Vlaeminck won San Remo three times (to Merckx’s seven). “I had a little less talent than Eddy on every level,” De Vlaeminck said. “But that will to win, that ‘always wanting to improve yourself,’ that was something I also had.”

Sean Kelly


To the European public, Sean Kelly was a huge star. But not even the continental journalists who’d known him for many years could fully penetrate his often robot-like exterior. One instance came in 1984 at the finish of the Tour of Flanders. After making the decisive counterattack half-an-hour from the finish, only four riders could stay with the Irishman around the 11-kilometer loop that ended the seven-hour battle over the cobbled hills and back roads of windswept Flanders. Two of the four contributed nothing to the pace—the Panasonic team’s Johan Lammerts and Ludo De Keulenaer—but they then started to attack in turn as the finish approached. Kelly chased each one down until Lammerts eventually went away unopposed.

The double-dealing of the Panasonic riders angered the Irishman. The press had never seen this side of the almost-too-placid Mr. Kelly. “That’s not the way to race,” he exclaimed in his excited, high-pitched, post-race voice. “What Lammerts and De Keulenaer did was scandalous. This defeat will rest heavy on my stomach.”

The media had never seen Kelly so angry. This was a new Kelly, a man who had only just begun to fully realize his great potential as a classics rider. Just six months earlier, at age 27, he took his first classics win, the Tour of Lombardy, by winning the tightest sprint in a decade ahead of a brilliant Greg LeMond, two of the best-ever Dutch classics racers Adri van der Poel and Hennie Kuiper, and Italian great Francesco Moser.

Now, after being the runner-up to Moser at the 1984 San Remo, here was Kelly taking second place in a monumental classic for the second time in two weeks. He was fired up about being beaten at Flanders, the only monument he didn’t win (he was second three times), but the main reason for his defeat was the overall weakness of his team. He spent the first five years of his pro career on Belgian squads where he was a secondary player to team leaders such as two-time world champion Freddy Maertens; and it was only when he raced for French teams from 1982 to 1988 that he was a team leader. But there was a trade-off: the teams were fairly low budget and Kelly didn’t have the back-up riders to support him at the classics.

Kelly would tell you that that suited him. He was not only a very strong, versatile bike racer—he won seven editions of Paris-Nice (every year on those French teams in the ’80s) and a Grand Tour (the 1988 Vuelta)—but he was also extremely smart tactically. Kelly knew how to play off one team against another, and because he had a tremendous finishing sprint, he knew that others would have to get rid of him from a breakaway if they wanted a chance of winning.

Had Kelly been a Belgian, he would have been better supported at the classics, and he wouldn’t have had to wait until the end of his seventh pro season to win his first monument. And without that “blank” start to his career. Kelly would no doubt have won all of the classics, and gotten closer to Merckx, Van Looy and De Vlaeminck in terms of total classics victories.

The final showdown

Of today’s top classics riders, Boonen has matched De Vlaeminck’s record of four Roubaix wins and he’s one of five men (including Magni, Leman and Johan Museeuw) to win Flanders three times; but Boonen went into this year’s classics season with no victories at San Remo, and he’ll never win the hilliest classics. Cancellara has won San Remo, Flanders and Roubaix, and he has expressed future ambition for tackling Liège and Lombardy, but at age 33, the big Swiss is unlikely to add those classics to his palmarès.

The only likely candidate to became the world’s best classics rider is Peter Sagan, who’s just 24 but has already won at Wevelgem, finished second at San Remo and Flanders and third in the Amstel Gold Race. The Slovak has tremendous speed at the end of long races and there’s no reason why he can’t develop into a rider similar to Kelly or De Vlaeminck.

One man who almost made our top-five list was Bernard Hinault, whose tremendous physical abilities enabled him to win all the Grand Tours and six of the nine top classics. And it was his unmatched fire that enabled him win a race he hated: Paris-Roubaix. But, as a Frenchman, Hinault was foremost a stage racer who lived for the Tour, while the classics remained like bonuses he could pick up on the way.

So who was X?


If we stage our virtual race, Coppi is riding in the famous celeste-green jersey of Bianchi alongside his brother Serse; Van Looy is wearing a world champion’s rainbow jersey at the head of his famous Red Guard (as his Faema-Flandria team was known); Merckx has an even stronger roster of teammates around him in the chocolate-brown colors of Molteni; De Vlaeminck, in the stars-and-stripes uniform of Brooklyn Chewing Gum, has just Belgian and Italian domestiques at his side; and Kelly, most likely in the red-and-white diagonal shirts of Skil, has the weakest support.

To give each of the five a course that will give each of them an opportunity to win, we’ve included various features of the five monuments: a couple of early climbs like those in Lombardy to thin out the field, a few bergs like the Oude Kwaremont in Flanders, some solid stretches of pavé like the Carrefour de l’Arbre cobblestones on the road to Roubaix, and a steep hill like Liège’s La Redoute before a flat final few kilometers into a San Remo-type sprint. Let’s call it The Monument.

Because each of these five racers has won at San Remo, Roubaix and Lombardy, we can expect them to all get over the early climbs and have enough teammates around to lead them out over the Flemish bergs before they reach the nasty sectors of Roubaix cobblestones. This is where the strength of Van Looy’s and Merckx’s teams come into play. Like Boonen’s teammates today, the Faema-Flandria and Molteni riders are strong enough to chase down the day’s early breakaway and also keep their leaders protected from the wind until they’re ready to make an aggressive move. At the same time, Coppi and Kelly are down to one teammate apiece and have to agree to a joint strategy to stop Van Looy or De Vlaeminck bridging to the latest breakaway before the decisive final hill.

But those two Belgians, good friends, do get away from the others. They know that they can’t climb as well as Coppi, Merckx and Kelly, and they hope their one-minute lead at the foot of La Redoute is big enough to keep them clear. Coppi, who knows he can’t out-sprint any of the others, goes for broke up the steep climb, passes De Vlaeminck and Van Looy before the summit and gets into his time-trial tuck for the remaining 15 kilometers of downhill and flat roads.

Behind him, a crafty Kelly has sat on Merckx’s wheel all the way up the climb and they catch De Vlaeminck on the descent, while Van Looy is left behind. The three chasers are all wary of each other, not sure which one has the fastest sprint. They vacillate. They know they have to work together if Coppi is going to be caught, but with 250 kilometers of extremely challenging riding in their legs, and a strong crosswind blowing, they also know that a solo effort to chase down Coppi has to be timed perfectly.

The gap has shrunk to 30 seconds with 5 kilometers remaining. Merckx knows he can’t wait any longer. He drops to the back as De Vlaeminck pulls through to the left…. And then Merckx strikes, moving to the right and making one of his signature accelerations. De Vlaeminck sees him too late, but the wily Kelly, having kept some gas in his tank, has the speed to dash past De Vlaeminck and catch Merckx’s wheel.

Happy that his two Belgian rivals have both been left behind, Merckx keeps working hard, with Coppi now in his sights up the straight road. Kelly, realizing that it will take two of them to join the campionissimo, begins to help Merckx. They flash under the flamme rouge with a kilometer left. Coppi is still 100 meters ahead. There are two 90-degree turn before the 400-meter-long finish straight, and with Coppi still ahead, the very smart Merckx knows he’ll have to jump out of that last turn, not only to catch Coppi but hopefully shed Kelly too.

This is where self-confidence and past results play their part. Merckx has won three world championships: he out-sprinted a small group in 1967, beat Gimondi in a two-man sprint in 1971, and finished solo in 1974. In Kelly’s best shot at the rainbow jersey, in 1989, he didn’t respond soon enough to LeMond’s long sprint and crossed in third. The Irishman is not going to make the same mistake, but when Merckx winds up the pace to overtake Coppi with 250 meters left, Kelly is gapped slightly. He begins to close. But the line comes too soon. Merckx is the winner, Kelly second and Coppi third; De Vlaeminck is a half-minute back in fourth, and Van Looy comes in fifth, warmly applauded by a massive crowd that has just witnessed history.

Eddy Merckx is “X,” the greatest classics rider of all time.

From issue 31.