Vincenzo Montella

"Whenever he played, even as a sub, he was always decisive."
-Eusebio Di Francesco

At the beginning of April in 1999, AS Roma president Franco Sensi sent Giallorossi fans wild when he released a statement during a Roma Club event in his honour: “I want to win, it's the only thing I care about because I'm just like all of you. And with this in mind, I have just signed a great footballer who is currently playing in Genoa. I can't say any more.” 

He didn't need to, however, as everyone knew the player he was referring to was Vincenzo Montella, more or less the dream target for every big Italian club at the time.

Montella's footballing career began in May 1987 when he successfully passed a trial that brought him into the youth set-up at Empoli. His first contract at the Florentine club earned him 400 thousand lire a month.

He made his first-team debut in 1990-91 and by the following season had established himself as a squad player in the senior team, training alongside players like Luciano Spalletti.

In 1995, Montella moved on a joint-ownership deal to Genoa C.F.C coached by Luigi Radice, who were then playing in Serie B. It was here, after scoring a wonderful acrobatic volley against Cesena, that Vincenzo first celebrated by imitating the flight of a plane.

Empoli sold him to Sampdoria the following season, by which time Vincenzo was already known as the ‘Little Airplane’. His first two goals in Serie A actually came against Roma at the Stadio Olimpico on 21 September, 1996.

He was signed as a Giallorossi player three years later and quickly became one of the fundamental building blocks of the squad that went on to win the title. In 2000-01, he scored 11 goals and some were absolutely vital as Roma closed in on their third-ever Scudetto.

The best of the lot must be his delicate chip against AC Milan in the match at the Stadio Olimpico, a stunning goal that only a player at the very top of his game could even attempt to do, let alone pull off at such a key moment of the campaign.
Vincenzo had become a figurehead of that Giallorossi team, so much so that on 18 December, 2001, he was chosen to present Alberto Sordi – an icon of the Eternal City – with a title-winning AS Roma shirt. This was an unforgettable honour for a man who would later have the satisfaction of starting his coaching career in the Giallorossi youth teams before he graduated to the senior side.