Alberto Contador

Alberto Contador stands as the most decorated grand tour rider of his generation, with 9 grand tour victories across 2 Tour de France, 3 Giro d'Italia, and 3 Vuelta a Espana titles — though some were later stripped due to doping sanctions. His 2011 Giro win featured a dramatic 6.2km mountain time trial Stage 16, where he bypassed main rival Vincenzo Nibali to seal the overall lead. Notably, his 2007 Tour de France victory came with an average speed of 38.7 km/h over the Pyrenean stages, a benchmark that exceeds the typical grand tour climber's performance. Despite the controversies, his grand tour tally remains unmatched among cyclists of the early 2000s.