The looks, the beard, the vineyard … New York City FC’s new star is a passionate aesthete – but he also won pretty much everything for Milan, Juve and Italy

With the Guardian’s unstoppable rise to global dominance (NOTE: actual dominance may not be global. Or dominant) we at Guardian US thought we’d run a series of articles for newer football fans wishing to improve their knowledge of the game’s history and storylines, hopefully in a way that doesn’t patronise you to within an inch of your life. A warning: If you’re the kind of person that finds The Blizzard too populist this may not be the series for you.

New York is the world capital of aging hipsters, so perhaps it’s no surprise that Andrea Pirlo is rocking up for New York City FC. To be fair, the 36-year-old heartbeat of Italy’s 2006 World Cup winning side deserves better than to be lumped in with all the desperadoes practising taxidermy and collecting Detroit techno on vinyl in their Williamsburg loft conversions. But then he does have the beard, a love of vintage fashion, his own vineyard, and an autobiography entitled I Think Therefore I Play. He’s not helping himself in that respect.

Andrea Pirlo taking his 'silent charisma' to New York City FC, Juventus confirm Read more

Pirlo is certainly the choice of the football hipster. He’s one of a dying breed who puts the emphasis on the aesthetic rather than the athletic. (“One part of my job I’ll never learn to love is the pre-match warm-up. I hate it with every fibre of my being. It actually disgusts me. It’s nothing but masturbation for conditioning coaches.”) He’s a deep-lying playmaker with wands for legs. A free-kick specialist. A stroller rather than a striver. And there’s the beard, the retro duds, the love of wine, the Descartes-referencing book ...

But none of this would mean much if he didn’t get results. He’s won pretty much everything there is to win as the heartbeat of Milan, Juventus and Italy for the last 15 years: all the domestic pots in Italian football, plus the Champions League, the Fifa Club World Cup, and Fifa’s actual World Cup.

To search for a signature moment is almost certainly to miss the point of Pirlo – the Guardian football writer Paul Doyle nailed it perfectly when he said “he isn’t about moment, he’s about a constant current running through matches” – but here we go anyway. He was named man of the match in the 2006 World Cup final victory against France, but his most telling contribution in that tournament was the decisive play in the semi-final against Germany. With just a couple of minutes of extra time remaining, the match was goalless, though it’d been a to-and-fro tussle of rare entertainment, 118 minutes of high-octane brilliance. The atmosphere febrile, penalties seemed certain. And penalties against Germany usually spells defeat. At which point Pirlo calmly sashayed across the front of the German box, left to right, decided against taking a rash long-range shot himself – a cool head while everyone else was losing theirs – and instead slipped a killer pass down the inside-right channel to set up Fabio Grosso for the winner.

Whether it’s Pirlo’s greatest assist in purely artistic terms is a moot point. He started his career as an attacking midfielder at Brescia, helping the club – perennial Serie B members – to promotion and a rare jaunt in Serie A. He earned a move to Internazionale, but couldn’t earn a permanent first-team berth, and was loaned back to Brescia, who had managed to secure the services of an aging Roberto Baggio. With the legendary Baggio in Pirlo’s attacking midfield role, Pirlo was shifted back to a deeper playmaking position, where he quickly started passing the ball like this:

A rare talent had been unearthed.

Pirlo eventually escaped Inter, crossing to city rivals Milan, where he quickly made his name. In 2002-03, Milan beat Juventus in the Champions League final. Pirlo was substituted in the final, and perhaps made more of an impression when Milan won Serie A the following season, chipping in with the odd preposterous goal.

Mio Dio!

Questo è il calcio!

Then the lowest point of his career: the absurd 2005 Champions League final defeat at the hands of Liverpool, a three-goal lead frittered away in the most complacent manner imaginable. Pirlo – who always looked like missing in the penalty shootout, untypically, for once, a shot bag of nerves – later described the horror of Istanbul as “a mass suicide where we all joined hands and jumped off the Bosphorus Bridge”. He also admitted that, having attempted to coin a pithy phrase with which to frame the match, could get no further than three little words: “For fuck’s sake!”

The 2006 World Cup more than made up for it. He was Italy’s man of the tournament – despite the best efforts of unlikely goalscorers Marco Materazzi and Fabio Grosso – scoring the opening goal of their campaign against Ghana, deciding the semi-final, dictating Italy’s best moments in the final, and calmly stroking his penalty in the shootout down the middle after Fabien Barthez in the French goal had committed himself.

Then the Liverpool wrongs were successfully righted in Athens. Milan met the Reds again in the 2007 Champions League final, and Pirlo made the crucial breakthrough, his free kick just before half-time deflecting off Pippo Inzaghi’s shoulder and wrongfooting Pepe Reina. Milan won 2-1, and Pirlo had his second Champions League medal. (Liverpool were the better side that day, just as Milan had been two years earlier in Istanbul. Funny how things work out sometimes.) Pirlo subsequently set up goals as Milan won the Uefa Super Cup and Fifa World Club Cup.

Pirlo won one more Serie A title with Milan, in 2011, but didn’t feature regularly in that campaign, his best years considered behind him. Seemingly a spent force, he was given a leaving gift of a pen, which he later complained had been “filled with banal blue ink”. Banal ink! The needle on the hipster-o-meter shears clean off. Pirlo paid Juve back by joining Juventus on a free, and winning four Serie A titles in a row.

Pirlo enjoyed another stellar international tournament at Euro 2012. He was again Italy’s star turn as they reached the final, where they were battered by Peak Spain. But his personal performance against England in the quarter finals was perhaps the highlight of the entire event. He played 131 passes in the match, a personal total which was higher than the combined efforts of the entire England midfield. Then in the penalty shootout, he floated a Panenka past Joe Hart, who was fannying around on the line in the style of St Vitus.

Pirlo would continue harassing Hart at the 2014 World Cup:

To his eternal credit, Hart congratulated Pirlo for the effort after the final whistle, freely admitting he had no idea where the ball was going.

There was no fairytale ending at Juventus in this year’s Champions League final, Pirlo at times suddenly looking his age against Barcelona. But four Serie A titles on the bounce - five if you factor in his last season at Milan – is not a bad way to go out. He’s now running down his career in MLS – but then they said he was all over when he left Milan, too, and look what happened after that.