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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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Chris Froome
Chris Froome won the Tour de France four times between 2013 and 2017, anchoring Team Sky's dominant run through cycling's biggest race during a decade when British cycling, historically a minor presence at the Tour, became one of the sport's most powerful forces. Froome's climbing style, an unusually high cadence combined with an aerodynamically unconventional but highly efficient position on the bike, made him one of the most recognizable riders of his generation, and his ability to attack decisively in the mountains while also holding his own in time trials gave him a complete skill set across the race's different stage types. His 2018 Giro d'Italia victory included an 80-kilometer solo attack on the Colle delle Finestre, one of the boldest and most unexpected winning moves in modern grand tour history, turning what looked like a losing position into the overall race lead in a single stage. Froome's career was interrupted by a serious 2019 training crash that left him with life-threatening injuries, and while he never fully returned to his previous form afterward, his four Tour titles across a five-year span place him among the most successful grand tour riders of the 2010s, a decade largely defined by his and Team Sky's methodical dominance.
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