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Jacques Anquetil
Jacques Anquetil became the first cyclist in history to win the Tour de France five times, taking titles in 1957 and then four consecutive years from 1961 to 1964, setting the benchmark that Eddy Merckx, Bernard Hinault, and Miguel Indurain would all eventually match or approach decades later. Anquetil was renowned as the finest time trialist of his generation, an era before dedicated aerodynamic equipment, and his ability to ride at a sustained, evenly paced effort over long individual stages — rather than relying on explosive mountain attacks — became the dominant strategic template other grand tour riders spent years trying to copy. His rivalry with French climber Raymond Poulidor, who never won the Tour de France despite finishing on the podium eight times, became one of French cycling's most enduring storylines — Anquetil's cool, calculated time-trial dominance against Poulidor's more emotionally embraced, ultimately unsuccessful climbing style. Anquetil also completed the rare Giro-Tour double in 1964, and his career total of five Tour titles stood as the record until Eddy Merckx matched it in 1974, making Anquetil the foundational figure in the sport's modern five-time-winner club that's still discussed as cycling's most exclusive tier of champions.
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Eddy Merckx
Eddy Merckx dominated professional cycling from the mid-1960s through the mid-1970s so completely that he earned the nickname "The Cannibal," a reflection of a competitive drive that pushed him to win races and stages even when a wiser tactical approach would have had him conserve energy for bigger goals later in a season. Merckx won the Tour de France five times (1969-1972, 1974) and, in his debut win in 1969, became the first rider in Tour history to win the general classification, points classification, and mountains classification in the same edition — a "triple crown" no other rider has repeated since. His career win total, 525 races across every discipline of professional cycling — stage races, one-day classics, and track events — remains the highest of any professional cyclist in history, a statistic that reflects genuine dominance across the entire sport rather than specialization in a single race type the way most great cyclists' careers are built. Merckx also won all five of cycling's "Monument" classics (Milan-San Remo, Tour of Flanders, Paris-Roubaix, Liège-Bastogne-Liège, and Il Lombardia), several of them multiple times, a combination of grand tour and one-day classics dominance that no cyclist before or since has matched, and that's central to why he's still almost universally cited as the greatest cyclist ever to race.
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