Chelsea’s Italian connection robbed of a game-changing Pirlo

There’s just something about Italians and Chelsea football club that seem to go together.

From Gianluca Vialli and Gianfranco Zola to Antonio Conte, Stamford Bridge has seen more than its fair share of Italian Premier League legends.

Conte is the latest Italian manager to win a Premier League title, and the prospect of another iconic Italian midfielder joining him on the Blues’ bench was mooted not that long ago: Andrea Pirlo. Idle speculation, in the end, but there was a time when the former Juventus and AC Milan midfielder looked poised to make his way onto the Stamford Bridge turf from the home dressing room.

Pirlo has always looked good in Azurri blue. In fact, Andrea Pirlo has always just looked good. And in 2009, there was another Italian manager on the Chelsea bench who knew just how good he’d look in Chelsea blue, too: Carlo Ancelotti.

Chelsea would go on to win the double that year, in the former AC Milan boss’s first season, but he’d have to do it without Pirlo. In his book, I Think Therefore I Play, the legendary midfielder recounts the his time at AC Milan, and how he twice failed to escape the club, forced to stay by owner Silvio Berlusconi, another man who knew just how good Pirlo was. One collapsed move was to Real Madrid, the other, Chelsea.

Ancelotti and Pirlo spoke at length, and the midfielder has spoken incredibly highly of his former coach, but the move broke down as Milan simply didn’t want to sell. They had already sold Kaka to Real Madrid, and had no intention of letting another superstar leave, too.

“He (Ancelotti) wanted to bring me to London at all costs, and cost was indeed the last hurdle still to be overcome. Insurmountable, as it transpired. Milan wanted too much cash, and they were also pushing for Branislav Ivanovic to be included in the deal.”

It was to be a frustrating outcome for Pirlo. Inter, by then about to be managed by Jose Mourinho, were dominant in Italy, winning five Serie A titles between 2006 and 2010. Milan, by contrast had lost Paolo Maldini to retirement, and just sold Kaka, the 2007 Ballon d’Or and still the last world Player of the Year who wasn’t Lionel Messi or Cristiano Ronaldo. Those departing giants were replaced by Oguchi Onyewu and Klaas-Jan Huntelaar.

Indeed, between the 2007 Champions League victory and leaving AC Milan in 2011, Pirlo only won one trophy – the 2010/11 Serie A title. It was only his second title in ten years with the Rossoneri. He’d win four in four years at Juventus.

And so it was that Andrea Pirlo never graced the Premier League, trapped in a sinking Milanese ship until rescue came in the form of Antonio Conte and Juventus, with whom he won more silverware.

The notion of Pirlo joining up with his former AC Milan manager in London in 2009 is a tantalising thought. Ancelotti’s reign at Stamford Bridge was characterised by two very different seasons. The first – the year Pirlo would have joined – saw Chelsea win the double, scoring 103 Premier League goals (still a record, though maybe not for long) and set a goal difference of +71 (also still a record). The second, they finished second and scored only 69 – their goal difference almost halved to +36.

In the Italian’s first season in charge, Didier Drogba finished as their top scorer with 29 league goals. The second season ended with Florent Malouda at the top of Chelsea’s goalscoring charts with just 13. The one area where they were consistent was in defence, conceding 32 goals in the first season and 33 in the second.

That second season, though, which led to Ancelotti’s sacking, is perhaps why the first isn’t today held in the high esteem it probably deserves. Last year, under Conte, part of the lore was that this was a side who played sparkling football, and who didn’t win the league by being the usual Chelsea – that is, the monster that Jose Mourinho created. But if it seemed like a new Chelsea, that would be to forget Ancelotti’s 2009/10 team, one that played even more sparkling football, breaking records along the way.

With a good defence already in place, it was really only the attack that let the Blues down in 2010/11. That’s why it’s tempting to wonder just how English football would have changed if Pirlo had arrived when his fellow countryman took the Chelsea job in 2009: would they have scored even more goals due to Pirlo’s passing range and setting of the tempo? Would they have conceded even fewer thanks to his ability to keep the ball and recycle possession?

Would he have revolutionised English football playing as part of a team who broke goalscoring records? Who says Italians are defensive?

In the Premier League era, when foreign imports became commonplace in English football, Chelsea have often had an Italian connection. The addition of Pirlo in 2009 was thwarted by AC Milan’s desperate attempts to stay at the top of Italian football, keeping their talismanic midfielder despite his desires to leave. And when eventually he did, to Juventus in 2011, Milan finally slipped, and their rivals from Turin have dominated ever since.

And that’s what the Premier League – and Chelsea in particular – missed out on. In 2010, Chelsea won the title but lost Pirlo. Milan kept their midfielder, but lost to Mourinho’s Inter. The next year, Chelsea finished second and sacked Ancelotti, but Pirlo won every Serie A title from then until his semi-retirement in New York. Most of them with Antonio Conte.

Who knows how many titles he would have won in London if Berlusconi hadn’t replaced his Ballon d’Or winner with Huntelaar.