He had participated in a breakaway during stage 4a, which won him sufficient time to hold the race leader's maglia rosa (English: pink jersey) for more than a week.

Twenty teams were invited by the race organizers to participate in the 1988 edition of the Giro d'Italia,[1] twelve of which were based outside of Italy.

[2] The teams entering the race were:[11] The starting peloton did not include the 1987 winner, Stephen Roche, who was sidelined for the majority of the 1988 season with a knee injury.

[2][4][12] Sala believed Jean-François Bernard came into the Giro in great shape and that the French rider could win the race if he could do well in the time trials and the mountains.

In addition, Bernard Hinault told Sala that if Jean Francois could do well in this edition of the Giro, he could one day lead a team in the Tour de France.

[12] Former Giro champion Gianni Motta thought Hampsten would win because of the effort he was expected to make on the Gavia Pass stage.

[13] Motta believed that Hampsten would excel there, while the Italian riders – the majority of the peloton – would not because they did not realize its difficulty and thought the Gavia was "just another climb".

[13][14] The 1986 Tour de France winner Greg LeMond entered the race with his PDM–Ultima–Concorde squad, after a break from cycling due to injuries sustained in a hunting accident.

[12] Swiss rider Tony Rominger also partook in the race and was considered by McGann and Sala as a dark-horse candidate for the victory after experiencing success at the beginning of his season.

[12] Before he injured his right knee earlier in the season during the Tour de Romandie,[4] many newspapers also believed Moreno Argentin to be a favorite to take several stages.

[12][15] Stampa Sera writer Curzio Maltese believed that Flavio Giupponi could take one of the stages containing many categorized climbs which award mountains classification points, if properly supported by his team Del Tongo–Colnago.

[3][4][12] The route for the 1988 edition of the Giro d'Italia was revealed to the public on television by head organizer Vincenzo Torriani, on 5 March 1988.

[29] In previous years, the organizers had made the race easier for the Italian favorites by including fewer hard climbs.

With the absence of Italian Francesco Moser from this edition, the race organizers included many famous and difficult climbs, such as the Gavia Pass.

[30] Moser himself stated that the route contained many difficult climbs and was not helping Italian cycling to prosper at a time when he believed it to be ailing.

[22] When asked about the route for the 1988 edition, 7-Eleven–Hoonved rider Bob Roll said "Those sons of bitches put every mountain they could find in the race that year.

[15] Gino Sala also felt the route was harsher than in years past and that the team time trial could influence the overall classification greatly.

[31] La Stampa writer Gian Paolo Ormezzano praised the route saying it was beautiful and well crafted but contained one flaw, in that the race did not finish in any major Italian city.

He also expressed his delight with the uphill time trial to Valico del Vetriolo as well as the inclusion of the Stelvio, Rombo and Gavia mountain passes.

[3] The Giro began with a 9 km (5.6 mi) time trial in the city of Urbino, which was won by Jean-François Bernard with a three-second margin over Tony Rominger.

[2][34] Guido Bontempi won the second stage and moved to third overall, while Bernard gained a five-second buffer over the second-placed rider, Rominger.

[39][41][42] As snow fell on the riders climbing the muddy roads of the Gavia,[39][40] Hampsten attacked at the base of the mountain but was chased by Erik Breukink, who eventually caught up and passed the American with seven kilometres (4.3 mi) to go.

[30][40] Although Breukink won the stage, Hampsten made the bigger story by becoming the first American to don the maglia rosa in the history of the Giro d'Italia.

[40][43][44] Conditions were so bad that one rider, Toshiba–Look's Dominique Gaigne, had to be carried on his bike into a shelter as his hands were frozen gripping the handlebars and former winner Giuseppe Saronni even stopped at a spectator's house and returned with a glass of the Italian liqueur Grappa.

[45] The start of the fifteenth stage was moved ahead from Bormio to Spondigna, because of snow covering the Stelvio Pass, but the summit finish in Merano was maintained.

[29][47] The sixteenth stage was marked by rain – which turned into snow as the peloton rose higher – and by two protests while climbing the Rombo Pass.

[82][83] Hampsten stated that Jean-François Bernard and Pedro Delgado both lacked awareness when attacking in the mountains and did not make the most of the time trials, but believed they would be more active in the Tour de France.

[30][39][40][52][89][90] According to CyclingNews writer Jason Sumner, a photo from the fourteenth stage depicting the future winner Andrew Hampsten climbing the Gavia while a snowstorm blows in the foreground has become a widely known image that even casual cycling fans would recognize.