Born in Livorno, Picchi started his by career playing for A.S. Livorno Calcio. In 1959 he moved to SPAL, before later at the peak of his time, and most of his career, at Milanese powerhouse F.C. Internazionale Milano.
He started to play in Internazionale as a right back, a role he previously held at SPAL. During the course of 1961-62 season, the legendary coach Helenio Herrera experimented by placing him as a Libero. The new position was successful; he became a strong figure at the defence, and indirectly set examples for teammates Tarcisio Burgnich and Giacinto Facchetti. During that time, Internazionale was still captained by Bruno Bolchi.
When Bolchi moved to Verona, Picchi was then selected as team captain. It was in his captaincy that Internazionale evolved into the era famously known as Grande Inter, when they won three scudetti, two European champions cups and two Intercontinental cups in the 1960s.
He played for two seasons at Varese before retiring at the age of 34.
He made his debut for Italy several months after becoming Intercontinental champions with Internazionale, in a 6-1 victory over Finland in November 1964. However, Italy coach at that time, Edmondo Fabbri, deemed him unsuitable for the team’s scheme, and subsequently left him out of the squad for 1966 World Cup in England.
Under the management of Ferruccio Valcareggi, he was regularly called for the qualifying matches of Euro 1968. Yet a fractured pelvis injury in a match against Bulgaria in April 1968, ruled him out of the competition, which concluded his last match with the Azzurri with 12 appearances.
After his playing career was over, he went on to coach Varese, Livorno, and then Juventus, but he died early because of cancer. The football stadium of Livorno is named after him.
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