There can be few regrets in football quite like the one AC Milan’s directors must feel following their decision to let Andrea Pirlo go to rivals Juventus in 2011.
Back then, the Italian international was 32 years old, and deemed too old and past his prime even at a club renowned for valuing the efforts of some of the game’s more elder statesmen.
Previously, similar aging luminaries the likes of Paolo Maldini, Clarence Seedorf and Pippo Inzaghi had all been granted a stay at Milan well into their mid and late thirties, but Pirlo was deemed not worthy of this luxury.
In the time since then, Pirlo may have aged two years, but he’s also added two Serie A titles, two Supercoppas and a European Championship runner-up medal to his trophy collection, with the domestic titles coming at the direct expense of Milan.
So it comes as no surprise that now that the maestro’s latest contract is coming to an end, that there are more than just a couple of clubs interested. And after his audacious Panenka penalty against England last summer at Euro 2012, a number of top Premier League sides are among those fluttering their eyelashes at the Italian.
According to reports from Italy, it is believed that Arsenal, Chelsea and Manchester United are monitoring the situation in Turin, while Spurs are even said to have already made their interest concrete with a preliminary contract offer.
The Italian press believe that Tottenham technical director Franco Baldini has been tasked with wooing his compatriot to White Hart Lane, with Andre Villas Boas keen on recruiting a deep-lying playmaker.
With the sale of winger Gareth Bale and the signing of a number of more central creative the likes of Paulinho and Christian Eriksen, AVB is evidently trying to make Spurs a narrower and more solid unit, with an emphasis on playing through the middle and on the break. Attracting someone of Pirlo’s quality, capable of distributing world class passes from just in front of defence would be an obvious advantage.
Given Milan’s mistake, however, Juve might yet be keen to tie down their chief creator for another year or two. Nor is there any guarantee that a player who has spent his career in Italy will be keen on such a drastic change in lifestyle at this time.
Nonetheless, with Baldini leading the charge and a three-year contract on offer, Spurs will be confident of persuading Pirlo to make the move, but will be keen to tie up any deal before the World Cup, knowing that another impressive showing on the international stage would bring only further competition for his signature.