Gordon Strachan must still lose sleep after missing Coventry City, Andrea Pirlo transfer chance | OneFootball

Coventry City's time in the Premier League at the turn of the century could have featured a legendary name

Every club has their what-ifs, stories from the past of potential transfers that could have been.

Leeds United fans will recall the fact that Erling Haaland once toured the training facilities at Thorp Arch, for example.

Coventry City learned in 2013 that back during the 1990s, the Sky Blues were close to signing Italian football legend Andrea Pirlo.

Gordon Strachan’s attempted move for young Andrea Pirlo

Strachan managed the Sky Blues between 1996 and 2001, initially starting as player-manager before retiring from his on-pitch duties.

Coventry were in the Premier League at the time of the potential move, although the Sky Blues suffered relegation from the top flight at the end of the 1999/2000 season.

As reported by the Coventry Telegraph at the time, Strachan took to social media to reveal that he had approached Pirlo’s agent over a reported move.

The Scot recalled: “When I was manager of Coventry I met up with Andrea Pirlo's agent to bring him to the club, when he was a youth team striker.”

At the time, Pirlo was still trying to make it as an attacker, playing in behind the striker for Brescia.

Pirlo, in fact, made his debut for Brescia at the age of 16 in 1995, a year before Strachan was appointed player-manager of Coventry.

However, during the 1995/96 season, Pirlo did not feature for Brescia’s first team, potentially explaining why the Italian was open to a move abroad.

The following campaign Pirlo was again a bit-part player for Brescia, who had been relegated to Serie B.

Pirlo was now slowly being dropped deeper into midfield, playing as a 10 rather than a second striker, taking him one step closer to his legendary future as a deep-lying playmaker or regista.

Tactical switch turns Andrea Pirlo into a star

By the time Strachan was sacked by Coventry City five games into the 2001/02 season, Pirlo had already played Champions League football, having featured for Inter Milan prior to joining arch-rivals AC Milan.

It was at AC Milan where Pirlo really ascended to star status, with Carlo Ancelotti deciding to move Pirlo from an attacking midfield role into a deeper position, where he could dictate play sitting in front of the defence.

Ancelotti said he was labelled “crazy” at the time, with fans and pundits unable to see the point of the tactical switch.

The legendary manager told COPA90: “I think that the player who I changed position, to whom it had the biggest impact was Pirlo.

“He was a number 10, and I've put him as a holding midfielder.

“Someone said to me that I was crazy, but the player believed that it was good for him to play there.

“So, he started to play there, and he was the best holding midfielder I have ever seen.”

In a decade with the Rossoneri, Pirlo lifted the Serie A title twice, alongside two Champions League trophies.

Whilst with AC Milan, he also lifted the biggest prize in world football – the World Cup, helping Italy to the trophy in 2006.

Even after 10 years with AC Milan, Pirlo maintained his dominance into his 30's - moving to Juventus in 2011 and winning four straight Serie A titles.

It seems farfetched that Strachan would have pulled off the same tactical masterstroke at Coventry, and the glut of trophies surely wouldn't have followed, although the Scot might still think about what could have been - as will the Sky Blues faithful.