We were never sure how close Andrea Pirlo came to joining Chelsea in 2009. The player had been heavily linked in the media, but it could have been one those cases of a story becoming popular through plausibility. Carlo Ancelotti had previously worked with Pirlo, and Chelsea could do with a player of his ilk, therefore Chelsea must be interested in signing the Italian. However, it appears that Pirlo might actually have been a lot closer to joining the club than we may have thought.

In Pirlo’s recent biography I Think, Therefore I Play, he revealed that he actually had agreed to join Chelsea in 2009. The midfielder spoke with the newly appointed Carlo Ancelotti and was keen to rekindle their relationship at Stamford Bridge. Only Berlusconi stood in the way of Pirlo gracing the Premier League with his talents. Berlusconi and suitcase full of money.

AC Milan had just lost their star player to Real Madrid, and the Italian media mogul couldn’t conceive letting Pirlo go in the same window. Berlusconi upped the asking price for the Italian and demanded the services of Branislav Ivanovic at the same. Chelsea couldn’t justify such an outlay for the 30-year-old and were forced to turn their interests elsewhere.

The midfielder that Chelsea eventually bought that summer? The 20-year-old Nemanja Matic. And although the club certainly made a mistake in letting the Serb go, they may not have been so desperate to sign him back if they had managed to bring in Pirlo all those years ago.

The sacking of Carlo Ancelotti after just two seasons in charge at Stamford Bridge is widely considered to be the harshest dismissal of the Roman Abramovich era. The Italian won the double in his first season in charge, setting a new record for goals scored in the Premier League in the process. In his second, the club finished runners up, and were still in with a chance of winning the league until they lost at Old Trafford in the 35^th game. Chelsea never got further than the quarter-finals in the Champions League under Ancelotti, and this is probably the factor that hurt the Italian the most, but the manager surely did enough to earn a third year at least.

However, the tone of Ancelotti’s second season was very different to the first. Where Chelsea once romped to the league title scoring 103 goals, much of the 2010/11 campaign was characterized by toil. The Blues often struggled to break teams down, and finished the season with 69 goals scored, 3 fewer than Arsenal in fourth.

The team was lacking in creativity in the centre of the park. In the summer of 2010, Chelsea let Joe Cole, Michael Ballack and Deco go, replacing the trio with one, in Ramires. And while the Brazilian has proved a successful the signing for the club, the midfielder does not have the passing range of any of the three he succeeded.

Ancelotti attempted to combat this problem by deploying Florent Malouda on the left of a midfield three to little success. The Italian also experimented by playing a midfield diamond with Nicolas Anelka at it’s head to similarly underwhelming results. And when Anelka wasn’t a makeshift No. 10, he often had to pretend to be a right winger. Chelsea had good players, but an unbalanced squad, and in retrospect, it must be concluded that Ancelotti did well to guide this team to second in the league.

Chelsea were in desperate need for a midfield passer of Pirlo’s class. Having won the league so spectacularly in 2010, their reward was to find 11 men behind the ball for much the following season. Against such teams, the advantages of having a player at the base of midfield who is as technically good as Pirlo are massive.

When faced with a compact defensive unit, a team needs to move the ball quickly across the pitch in order to find space. This is what Pep Guardiola’s teams are often attempting to do. Although the play may not look positive as the ball  moves laterally, or backwards, what they are attempting to do is stretch the opposition defence. And over the course of 90 minutes, they often achieve their goals.

The player that Chelsea had in this position is John Obi Mikel. And while the Nigerian may be a lot of things, a quick passer of the ball is not one of them. The result was frequently laborious performances from Ancelotti’s Chelsea just a season after they’d been labelled the great entertainers.

Had the club managed to sign Pirlo as Ancelotti had requested when he got the job, things would likely have turned out very different for both manager and club. It certainly seems unlikely that the team would have struggled so much to create in the Italian’s second season, and therefore probable that he would have got a third in charge.

If Andrea Pirlo had signed for Chelsea, it’s unlikely that the club would thought it necessary to spend £50m on Fernando Torres in an attempt to increase the amount of goals scored, and we all could have been spared the tragedy of the £50m man. There may have been no AVB, no RDM, and no Champions League.

However, this is all hypothetical. The more important point to consider is that if Chelsea had identified Pirlo as the type of player they needed in 2009, why have they still not managed to sign such a player in the previous five years. In light of the team’s continued struggles to break down teams that defend deep this season, a player of Pirlo’s passing ability would have been sorely welcomed.

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