Between 1946 and 1951 a special jersey was awarded to the last cyclist in the general classification of the Giro d 'Italia, called Maglia Nera.
The idea came from a story in the 1920s. A football player, called Giuseppe Ticozzelli was such a cycling enthusiast, that he attended the race as an individual rider in 1926.
Individuals were common in the peloton of the grand tours in the early years. They had no helpers, no supporting crew; and the most extraordinary stories usually happened with them. Because they had to care about themselves, it wasn't a big surprise when they dropped early from the race and finished a stage several hours after the majority of the peloton. Ticozzelli completed only 3 stages and gave up the race, but probably because he was a football player he has got more publicity than other individual competitors.
And he was wearing a black jersey.
The award called "Maglia Nera" was introduced to the Giro d'Italia in 1946.
Luigi Malabrocca won it twice (1946 and 1947). He was really fighting for the last place of the race. He was strong, and an excellent cyclocross rider by the way, but he was a typical domestique, who never had a chance to win an important road cycling race.
In 1949 he had a real strong (but in this case better to say a weak ) rival, Sante Carollo, a rider who had the chance to ride the Giro in the last minute. Carollo wasn't on the level of the other riders of the peloton, he dropped easily. But Malabrocca wanted to win this special jersey, so he tried to lose as much time as possible by hiding in barns and taverns or even by puncturing his own wheels. Yet, at the end of the race, the jury gave Carollo the jersey.
Malabrocca's performance was the reason why the jersey wasn't awarded anymore since 1952.
He managed to ride a 40 km long road between Novara and Milano in 3 hours and 15 minutes.
It seemed to be rather a joke, not a competition.
By the way, the last winner of the Maglia Nera was Giovanni Pinarello, who used the prize money to establish his famous cycling company.
Winners of the jersey:
1946 Luigi Malabrocca (Milan-Gazzetta)
1947 Luigi Malabrocca (Welter)
1948 Aldo Bini (Benotto)
1949 Sante Carollo (Wilier Triestina)
1950 Mario Gestri (Bartali)
1951 Giovanni Pinarello (Bottecchia)
Leadpic: Luigi Malabrocca at the Giro d'Italia 1947