Chelsea

The one that got away: Andrea Pirlo and Chelsea

What a joy it would have been if Andrea Pirlo, one of the most gifted footballers in the world, brought his creative talents to the Premier League in 2009.

The Premier League has housed some of the classiest talents known the mankind in its time, including the likes of Dennis Bergkamp, Paul Scholes, Thierry Henry, David Silva, Frank Lampard, Steven Gerrard, among many, many more. However, we will always be left wondering what could have been when it comes to the classiest of them all, Andrea Pirlo.

Andrea Pirlo – 2009 

The World Cup winning midfield maestro was playing for AC Milan at the time of interest and Chelsea were in pole position to sign him when they agreed a deal with compatriot Carlo Ancelotti, someone whom Pirlo considered a father figure.

“It was August 2009 and I’d reached agreement with Chelsea, the club where Ancelotti had just come in as manager,” Pirlo told us in his autobiography – I Think Therefore I Play (via Sky Sports).

“Carlo was like a father and a teacher for me, a kind, friendly man who knew how to make things fun.

“I’d spent the best years of my career with him. If you’re a player who wants to get on and give everything, you won’t find anyone better than him.

“Carlo Ancelotti was my motivation for agreeing to head to London. But, in the meantime, Berlusconi had pulled out a second piece of paper.”

He continued to cite how Silvio Berlusconi, former owner of Milan, convinced him to stay: “Listen, Andrea, you just can’t do this, damn it. You’re the symbol of Milan, a standard bearer for this team, and we’ve already sold Kaka. You can’t jump ship as well. It’d be a terrible blow, to our image as much as anything. We can’t have everyone leaving.’”

Classic Berlusconi ruining our fun and preventing an ungodly combination of Michael Ballack, Frank Lampard, Michael Essien, Deco and Andrea Pirlo all in the same team. Imagine. Maybe he was doing the Premier League a favour; maybe it was an act of mercy, a protection for us mere mortals who wanted to see our respective beloved sides stand even the slimmest of chances.

The Italian would move to Juventus two seasons later after helping AC Milan to a domestic title, helping the Turin giants secure four consecutive Serie A cups before moving to New York City where he retired in 2018.

To Top