Tom Simpson (1965)

Wearing the rainbow jersey as World Road Race Champion, Tom Simpson of team Peugeot-BP-Michelin did as much as anyone in contributing to the modern superstition held by some that there is a "curse of the Rainbow jersey". The very first Briton to win the World Road Race Championship after prevailing over Rudi Altig of Germany in a sprint to the finish at San Sebastián in 1965, Simpson, who had been riding in top form that year, subsequently broke his leg badly in an off-season skiing accident which effectively crippled his entire 1966 campaign, most of which was lost to extensive rehabilitation. The very next year, while climbing the 21 kilometers of stone slope that punctuate Mount Ventoux during none other than the 13th stage of the 1967 Tour de France, Simpson collapsed from diuretic induced heart failure and tragically died despite almost immediate medical attention - making him the first of at least four winners of the Rainbow jersey (...the others being Jean-Pierre Monseré in 1971, Rudy Dhaerens in 1998, and Issac Gálvez in 2006) to meet a similarly premature end.