Andrea Pirlo & the thirty-something stars who were released too early by their clubs

In honour of the evergreen Bianconeri midfielder, has put together a list of players presumed to have been past their best but who went on to shine elsewhere
By Mark Doyle

In his first term at Milanello, Massimiliano Allegri led AC Milan to their first Serie A title in seven years. Going into Saturday's eagerly-awaited clash with Juventus, the Rossoneri sit top of the Serie A standings. Only last week, the reigning Italian champions routed Arsenal 4-0 in the first leg of their Champions League last-16 tie at San Siro.

With all of this in mind, it seems almost perverse to question Allegri's judgement. And yet, with the resurgent Bianconeri in town this week, it is impossible not to raise the issue once more: just why on earth did the Rossoneri coach allow Andrea Pirlo to leave the club on a free transfer last summer?

Allegri may not have had the final say on the matter but he undoubtedly should have fought harder to hold on to the veteran playmaker, who has arguably been the outstanding player in Serie A this season.

Pirlo's peerless performances have made Milan, and indeed Allegri, look foolish. It would, of course, be of little consolation to either should the Italy international go on to lift the title with Juve, but their dreadful gaffe is not without precedent.

Indeed, as has discovered, numerous clubs and coaches have offloaded players they thought were well past their sell-by-date, only to watch in disbelief as they aged like a fine wine.

So, in alphabetical order, and with apologies to those who failed to make the cut, including Cafu, Jocelyn Angloma, Fabio Cannavaro, Youri Djorkaeff, Gordon Strachan, John Aldridge, Ruud Gullit and Ray Clemence among others, here is our list of the ones who should never have gotten away ...

ROBERTO BAGGIO (AC Milan to Bologna; Inter to Brescia)
Roberto Baggio knows a thing or two about crossing divides, having caused quite a furore in Florence when he made the move from Fiorentina to Juventus in 1990.

'Il Divin Codino' also lined out for the two Milan clubs during his nomadic career and while Baggio never settled during either spell at San Siro, he made both look foolish for letting him leave.

In the first instance, the former Italy international scored 22 goals in 30 games for Bologna after being let go by AC Milan in 1997. It was on the back of that wonderful campaign that Inter decided to bring Baggio back to the Giuseppe Meazza the following summer.

However, the trequartista again looked out of place at San Siro and he was moved on to Brescia in 2000, where he promptly rediscovered his goal-scoring touch, netting 45 times in 95 appearances for the provincial outfit before eventually riding off into the sunset in 2004.

PETER BEARDSLEY (Liverpool to Everton)
Scoring in a derby is undoubtedly the best way to get the fans on your side, as Peter Beardsley knows only too well.

A legend at Liverpool, the forward was inexplicably told that he had no future at Anfield by new manager Graeme Souness in the summer of 1991. The Scot felt that Beardsley was finished and promptly offloaded him to city rivals Everton for £1 million. It was a gross error of judgement, the kind of which Souness specialised in during his time in charge of Liverpool.

Beardsley enjoyed two successful seasons at Goodison Park - joining a select group of players to score for both Merseyside clubs in the derby during that time - before going on to make a complete mockery of Souness’ decision to sell him over the course of a wonderfully productive spell with Newcastle. Dean Saunders, meanwhile, the man bought to replace Beardsley, lasted just a year at Anfield before being moved on to Aston Villa.

PAT JENNINGS (Tottenham Hotspur to Arsenal)
They say you should never make the same mistake twice - and yet Spurs did just that when they allowed Pat Jennings to leave for Arsenal in the summer of 1977.

The Irishman had established himself as one of the game’s top goalkeepers during his 13 years at White Hart Lane, winning the FWA Player of the Year award in 1973 before then becoming the first goalkeeper to collect the PFA version of the award three years later. Truly remarkable, then, that Spurs decided to offload Jennings to their rivals the following year.

Tottenham eventually managed to bring the Northern Ireland international back to the Lane – but not until 1985, by which time the then 40-year-old Jennings had racked up 237 appearances for the Gunners and established himself as a hero to fans on both sides of the north London divide.

MIROSLAV KLOSE (Bayern Munich to Lazio)
Miroslav Klose has a long away to go before he reaches the cult-hero status some of the other players on this list have achieved, but the German has certainly made a massive impact since arriving at the Stadio Olimpico last summer.

Deemed surplus to requirements at Bayern Munich, the forward parted company with the Bavarians when his contract expired at the end of last season. Lazio snapped Klose up on a free transfer but the 33-year-old’s signing was still seen as something of a risk given the striker, in spite of his fine record at international level, had never before played for a club outside Germany.

However, Klose wasted little time in proving himself in Serie A, scoring just 12 minutes into his league debut after leaving AC Milan's renowned defender Alessandro Nesta trailing in his wake. The goals have not stopped coming since and he had already established himself as a favourite with the Biancocelesti by the time he netted an injury-time winner in the first Rome derby of the season.

DAVE MACKAY (Tottenham Hotspur to Derby County)
Dave Mackay was a key component in Tottenham Hotspur’s double-winning side of 1961 and the Scot was a firm favourite of the White Hart Lane faithful for nearly a decade.

However, by 1968 it was thought that Mackay's legs had gone and he was allowed to join Derby County for £5,000. The left-half-turned-sweeper excelled during his first season at the Baseball Ground and inspired Derby to promotion to the top flight, a feat which saw the then 34-year-old named the Football Writers’ Association (FWA) Player of the Year in conjunction with Manchester City’s Tony Book.

Unfortunately, Mackay had departed by the time Derby claimed the old First Division title but, as outlined in ‘The Damned United’, Brian Clough’s decision to sign Mackay was one of the catalysts in Derby’s remarkable transformation from Second Division also-rans to champions of England.

GARY McALLISTER (Coventry City to Liverpool)
Not many 36-year-old footballers are expected to play a key role for their clubs in the final of a European competition, but Gary McAllister did just that in the 2001 Uefa Cup decider. Indeed, the veteran midfielder had been the best player on the pitch in Liverpool’s enthralling 5-4 victory over Alaves at the Westfalenstadion. The Scot scored one goal, from the penalty spot, and also had a hand in three others, including the winner.

The former Leeds United man’s heroics in Dortmund had come as no surprise given how influential he had been over the course of Liverpool’s season but it easy to forget that most pundits, and indeed supporters, had expected him to prove nothing more than a bit-part player after being picked up on a free transfer from Coventry City the summer before.

Ultimately, McAllister played just one more year for the Reds before returning to Highfield Road but he remains one of Anfield’s most loved – and most unlikely – cult heroes.

RAUL (Real Madrid to Schalke)
When it comes to achieving iconic status at a club in double-quick time, Raul surely holds the record. A genuine living legend on account of his exploits with Real Madrid, the former Spain international finally parted company with Los Blancos in the summer of 2010.

Despite lucrative offers from elsewhere, Raul elected to link up with the Bundesliga outfit in order to continue playing in the Champions League, thus presenting him with the opportunity to claim the all-time scoring record in Uefa competitions.

The forward did just that during a remarkable European campaign in which Schalke defied all odds in rampaging their way into the semi-finals with a stunning 7-3 aggregate win over defending champions Inter.

The Germans eventually bowed out to Manchester United but Raul, less than 12 months after leaving the Santiago Bernabeu, had already achieved a similar level of adulation at the Veltins-Arena - thanks in no small part to his decision to jump into stands to celebrate Schalke’s elimination of the Nerazzurri with the fans.

While Roberto Baggio failed to establish himself in Milan, Frank Rijkaard is still remembered as one of the finest players to have ever represented the Rossoneri. Although the Dutchman was the least celebrated member of arguably the most influential triumvirate in the history of Italian football, Rijkaard was just as important to Arrigo Sacchi’s all-conquering Milan side of the late 80s/early 90s as his compatriots Ruud Gullit and Marco van Basten.

By 1993, though, Rijkaard no longer seemed the incredibly dynamic force of old and he was given permission to return to Ajax. It was a decision that would come back to haunt Milan – in the most dramatic fashion.

Along with fellow veteran Danny Blind, Rijkaard added experience and savvy to an Ajax squad boasting an almost freakishly talented crop of youngsters. Louis van Gaal’s side won back-to-back Eredivisie titles before claiming the Champions League in 1995 - against the Rossoneri - with a late goal scored by Patrick Kluivert but created by the 32-year-old Rijkaard, who was making his final appearance as a pro.

MARK VAN BOMMEL (Bayern Munich to AC Milan)
The Rossoneri may have erred in allowing Pirlo to leave, but the club pulled off a masterstroke in acquiring the services of Mark van Bommel midway through last season.

The abrasive Dutchman was a free agent having rescinded his contract with previous employers Bayern Munich but his sudden availability did not exactly arouse the interest of Europe’s elite. However, Milan decided to take a low-risk punt on the former PSV ace, signing Van Bommel on an initial six-month deal. The gamble paid off – and how.

Despite getting sent off on his Serie A debut, against Catania, Van Bommel immediately looked at home in the slower-paced environs of the Italian game and quickly became a permanent fixture in Allegri’s starting line-up, playing an integral role in the club’s first Scudetto success in seven years. His reward was a new one-year contract at the end of the season - as well as the knowledge that Bayern had struggled terribly without him.

GIANFRANCO ZOLA (Parma to Chelsea)
It is fair to say that Gianfranco Zola is a revered figure at Stamford Bridge on account of his exhilarating displays for Chelsea during a seven-year stay in west London.

The diminutive Italian joined the Blues from Parma in 1996 for a fee of €4.5 million, which, at the time, seemed like a lot of money for a forward six months the wrong side of 30, particularly one that then Gialloblu boss Carlo Ancelotti could find no room for at the Ennio Tardini. However, Zola proved one of the great bargain buys of the modern era.

Indeed, the former Napoli protege lit up the Premier League and was FWA Player of the Year at the end of the season – a remarkable achievement given he had arrived just under four months into the campaign.

Zola collected four major trophies during his time at Stamford Bridge but it would be a mistake to measure his impact in terms of silverware because his most significant achievement was pushing a pre-Abramovich era Chelsea back towards the forefront of English football.