By the time of the 2002 UEFA European Under-21 Championships in Switzerland, Massimo Maccarone had already made headlines by becoming the first Serie B player in 20 years to play for the full Italian national side. The 22-year-old striker had come on as a 75th minute substitute in a 2-1 win over England at Elland Road, earning a stoppage-time penalty when brought down by keeper David James, which Vincenzo Montella promptly despatched for the winner.
Maccarone started his career with AC Milan, where he did not make a first team appearance, and was subsequently loaned out to several lower league clubs. It was not until his transfer to Empoli in 2000 that he really began to get noticed, scoring 24 goals in 68 appearances for the Tuscany club and helping them get promoted to Serie A in his second season.
However, the game which really brought him to prominence around Europe was the Group A Under-21 fixture with England in Basle on May 20, 2002. The Italians – under the notorious Claudio Gentile – had disappointed in their first group match, a 1-1 draw with Portugal, and England went into the encounter as slight favourites having beaten the hosts 2-1 in Zurich. But it was Maccarone that stole the limelight with a two-goal salvo that put paid to England’s hopes of topping the group.
The first-half had finished goalless, but a dull encounter was brought to life in the 58th minute when Maccarone took advantage of a deflection off Chris Riggott to curl the ball home with the outside of his foot. The lead lasted just six minutes, England skipper David Dunn crossing superbly for Gareth Barry to volley the equaliser past keeper Ivan Pelizzoli. Nonetheless, with time running out Maccarone capped a magnificent personal display late on by turning Riggott inside out and crashing home a left-foot drive for a 2-1 victory.
His prowess in front of goal had not gone unnoticed, with Chelsea favourites to sign him, but Middlesbrough manager Steve McClaren eventually snapped him up for a fee of over £8m. Having made a fine start on Teesside he earned a further international cap as a substitute against Wales – his only other appearance – but from that point he failed to justify his price tag and was loaned out to both Parma and Siena.
He returned to Middlesbrough for the 2005/06 season but in January, 2007, having scored 18 goals in 81 league appearances, went back to Siena on a free transfer, with Boro´ chairman Steve Gibson calling him a “fool” after he had criticised McClaren. His second spell at Siena was more successful, with 34 goals in 102 games, but when they suffered relegation in 2010 he moved to Serie A club Palermo, where he scored just two goals before being transferred to Sampdoria in January 2011.
Whether the big-money move to England ultimately proved his undoing is debatable, but what is not in doubt is that Maccarone never realised anything like his true potential.