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Still to replace Paolo Maldini - AC Milan's fruitless search for a top-class left-back goes on
It has been abundantly clear for nearly a decade now that the Rossoneri needed to find a worthy successor to the legendary Italian defender - and yet they are still looking
Jan 29, 2012 9:00:00 AM
Getty Images
ANALYSIS
By Mark Doyle
When Paolo Maldini retired from the game in the summer of 2009, the club which he had served for all 24 years of his majestic playing career, AC Milan, paid the defender the ultimate tribute by retiring the No. 3 jersey which he had worn with such distinction. It was just as well, really, because, three years on from his retirement, the Rossoneri have yet to find a single player worthy of wearing Maldini’s shirt.
It is not as if Milan have not been trying, either. Indeed, the search for a successor began long before the former Italy international hung up his boots. Replacing a living legend is no mean feat but, as one can see from below, Milan’s attempts to do so have been, for the most part, haphazard at best, with Lecce's Djamel Mesbah just the latest attempted solution ...
When the Czech arrived, Maldini was still club captain and Milan’s first-choice left-back but, at 35, it was becoming evident that he was no longer able to get up and down the flank like he once did.
Versatile, dynamic and blessed with a wonderful left foot, Jankulovski, an €8.5 million signing from Udinese, seemed like the ideal replacement, a modern full-back for the modern era. He took time to settle but his gradual adaption to his new surroundings ultimately enabled Milan to redeploy the ageing Maldini in the centre of defence.
However, while Jankulovski enjoyed a couple of productive seasons at San Siro, he never really nailed down a regular berth - either at full-back, wing-back or on the left-hand side of midfield - during his six years with the club.
Kaladze, of course, had already been at Milan for four years at this stage but, despite impressing during his first few seasons as a centre-half, he was never considered the ideal foil at the heart of the Rossoneri defence for Alessandro Nesta.
Indeed, by 2005, he had developed into something of a utility player and was often used to fill in for Maldini at left-back. Maldini’s eventual conversion into a centre-half meant even more game time for Kaladze on the left-hand side of the back four but, being slow and cumbersome, he never looked at home there. No tears were shed when he left for Genoa in 2010.
A destitute man’s Roberto Carlos, Serginho had his moments in a Milan jersey but there was always the view that the Brazilian was not skilful enough to play as a winger and not disciplined enough to play at full-back. Consequently, after a couple of exciting seasons following his arrival in 1999, he became relegated to the role of impact substitute.
Going into the 2005-06 season he was 34, just a year younger than Maldini, and, with both his pace and his stamina having already diminished considerably, he was most certainly not considered a viable solution to Milan’s need for a reliable left-back.
Snatched away from Monza as a youngster, Antonelli had spent just a couple of years in Milan’s youth team when he was handed his senior debut as a 19-year-old in a Coppa Italia clash with Brescia in November 2006. He made his Serie A bow the following month, against Udinese, and hopes began to grow that Milan had unearthed Maldini’s heir from within.
Antonelli, though, would never play another league game for the Rossoneri, which was bizarre, really, given that he impressed sufficiently on a loan spell with Bari the following season to eventually secure a permanent move to Parma. Did Milan discard ‘the new Maldini’? No, of course not. But one wonders how Antonelli, who is now at Genoa, would have developed if he had been afforded more time and patience at San Siro.
Signed on a free transfer from city rivals Inter, Favalli, 34 at the time, was not exactly the future. He was, however, a potential stop-gap solution for the present. Indeed, the Rossoneri certainly had nothing to lose by offering a home to an experienced and versatile defender who had been a tremendous servant of Lazio’s.
However, despite endearing himself to the fans with goals in successive games during the 2006-07 campaign, against Messina and Empoli, ‘Favallino’, as he was christened by the Rossoneri faithful, was never really anything more a steady performer at full-back and a useful squad player.
Darmian, a defender who could play anywhere across the back four, made his Milan debut in a Coppa Italia clash with Brescia in November 2006 at the age of just 16. The parallels with Maldini were already obvious. The youth-team player would have to wait until the end of the season to make his first appearance in Serie A, as a substitute in a home defeat by Udinese, but it seemed that Milan had a real prospect on their hands.
But Darmian would not surface in Serie A again until the 2008-09 campaign – and, even then, only as a substitute – and, after spending the following season on loan to Padova, he joined Palermo in a co-ownership deal in 2010. Currently on loan at Torino, it now looks a long way back to San Siro for the now-22-year-old Darmian.
Milan signed Grimi during the January transfer window, paying Racing Club €2m for the services of an Argentine left-back with an Italian passport. His first outing for the Rossoneri came in the Coppa Italia, against Arezzo, and he made his first appearance in Serie A in April when he came on for the final 10 minutes of the 5-2 win over Ascoli. Grimi featured twice more before the season’s end before being loaned to Siena for the first six months of the following campaign.
He failed to shine at the Artemio Franchi, though, and was sold to Sporting CP in January 2008 after it had become abundantly clear that he was not cut out for Serie A. It became evident that he wasn’t much cut out for the Primeira Liga, either, and he is now on loan at Genk.
Kaka is still fondly remembered by the Rossoneri faithful; his younger brother is not. After spending a season on loan at San Siro from Sampdoria, Digao was signed on a permanent deal in 2005 but he was immediately famed out to Rimini. The hope was that he would develop at the coastal club over the next two seasons; he did not.
After being recalled in the summer of 2007, Digao made his debut for the club in the Coppa Italia clash with Catania at the tail end of December. His first - and only - appearance in Serie A came later in the season against Lazio when he was brought on at during the interval for the injured Jankulovski. Given he never looked like much of a centre-half, there was little chance of him excelling in an unfamiliar position - and he did not. Digao never played for Milan again and eventually rescinded the final year of his (six-year!) contract with the club in 2010. Shockingly, he is now without a club.
Having failed to settle in Barcelona after deserting a sinking ship at Juventus in 2006, Zambrotta returned to Italy in time for the start of the 2008-09 campaign after Milan agreed to pay the Catalans €10.5m for the versatile defender. With the Rossoneri still looking for a reliable left-back, the Italy international looked a perfect fit. However, while Zambrotta was a regular during his first season back in Serie A, he has become increasingly marginalised, partly because of injuries but also because of inconsistent form.
He remains Milan’s most accomplished left-back, but then that is not saying much. Indeed, while his versatility has often been a major plus for Milan, it is hard not to conclude that the Rossoneri bought a player whose best days were already behind him. His current tally of 80 appearances in just under four seasons does not represent a good return on €10.5m.
Antonini began his career at Milan but spent the guts of eight years moving from club to club, usually on loan, before returning to San Siro via Empoli in 2008. Obviously, his arrival coincided with that of Zambrotta and it was inevitable that he would have to play second fiddle to the World Cup winner for a while.
However, if Antonini had excelled, the versatile Zambrotta could have been switched to the right flank. As it was, Ignazio Ibate made the right-back position his own with the kind of consistency and intelligent positional play that were so conspicuous by their absence in Antonini’s performances. Antonini is still at Milan, of course, but it is telling that he was recently linked with a move during the current transfer window.
A product of the club’s youth system, De Vito was still a member of the Milan primavera when the season began, but he was given his first-team debut by then-coach Leonardo in a 2-1 victory over Novara in the last 16 of the Coppa Italia. His Serie A bow followed in April when he was thrown on for Jankulovksi for the last 10 minutes of a disappointing 3-1 defeat in Palermo.
Leonardo then departed, which proved a disastrous development for De Vito. Indeed, he did not feature once under new boss Massimiliano Allegri during last season's title-winning campaign and the 20-year-old full-back is now out on loan at Cittadella. A spell in Serie B might do him the world of good but it remains to be seen if he has a future at Milan under Allegri.
When Milan acquired Emanuelson from Ajax during last year’s January transfer window for a reported fee of €1.7m, it was hoped that he would provide some much-needed pace and dynamism down the left-hand side. To be brutally honest, he has provided neither.
In his defence, his versatility has proven something of a hindrance to his attempts to establish himself at Milan because he has never really been afforded a decent run of games at full-back or on the wing. What is bizarre, though, is that, having shown little promise in either position, he has recently been tried out in the trequartista role. The Dutchman still has time to prove himself at San Siro but it now seems highly unlikely that it will be as a left-back.
Vila had played just 24 times for Espanyol when Milan decided to pay a reported €4m to bring the then 21-year-old to San Siro during the 2010 January transfer window. A regular in the Spanish Under-21 squad, Vila was considered one of his country’s most promising young defenders.
However, less than 12 months after his arrival in Italy, he was already on his way back to Espanyol on loan, with Milan having decided after just one appearance in Serie A, against Udinese on the final day of the season, that he was not yet ready for Italian football.
The chances are that his move will become permanent but, in light of his performances in La Liga this season, Milan would be well advised to avoid letting a young full-back of real potential move on without having really given him a proper crack of the whip.
It is remarkable to think that last summer two of European football’s genuine heavyweights, Real Madrid and Milan, were battling out for Taiwo’s services ... Now, he’s at QPR. The Nigerian defender made his name in France with Marseille as a hard-running left-back with a powerful strike and was considered one of the most attractive frees on offer during the last transfer window. Indeed, the Rossoneri were pretty pleased with themselves when they announced his signing last May.
Now, though, it looks like a gross error of judgement. Indeed, after making his Serie A debut against Cesena at the tail end of September, the 24-year-old defender featured only three more times in the league as Milan boss Allegri quickly realised that the search for a successor to Maldini’s throne must go on. Over to you, Djamel Mesbah ...
By Mark Doyle
When Paolo Maldini retired from the game in the summer of 2009, the club which he had served for all 24 years of his majestic playing career, AC Milan, paid the defender the ultimate tribute by retiring the No. 3 jersey which he had worn with such distinction. It was just as well, really, because, three years on from his retirement, the Rossoneri have yet to find a single player worthy of wearing Maldini’s shirt.
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It is not as if Milan have not been trying, either. Indeed, the search for a successor began long before the former Italy international hung up his boots. Replacing a living legend is no mean feat but, as one can see from below, Milan’s attempts to do so have been, for the most part, haphazard at best, with Lecce's Djamel Mesbah just the latest attempted solution ...
| SEASON 2005-06 |
| MAREK JANKULOVSKI |
 Read more on Jankulovski |
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Versatile, dynamic and blessed with a wonderful left foot, Jankulovski, an €8.5 million signing from Udinese, seemed like the ideal replacement, a modern full-back for the modern era. He took time to settle but his gradual adaption to his new surroundings ultimately enabled Milan to redeploy the ageing Maldini in the centre of defence.
However, while Jankulovski enjoyed a couple of productive seasons at San Siro, he never really nailed down a regular berth - either at full-back, wing-back or on the left-hand side of midfield - during his six years with the club.
| KAKHA KALADZE |
 Read more on Kaladze |
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Indeed, by 2005, he had developed into something of a utility player and was often used to fill in for Maldini at left-back. Maldini’s eventual conversion into a centre-half meant even more game time for Kaladze on the left-hand side of the back four but, being slow and cumbersome, he never looked at home there. No tears were shed when he left for Genoa in 2010.
| SERGINHO |
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Going into the 2005-06 season he was 34, just a year younger than Maldini, and, with both his pace and his stamina having already diminished considerably, he was most certainly not considered a viable solution to Milan’s need for a reliable left-back.
| SEASON 2006-07 |
| LUCA ANTONELLI |
 Read more on Antonelli |
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Antonelli, though, would never play another league game for the Rossoneri, which was bizarre, really, given that he impressed sufficiently on a loan spell with Bari the following season to eventually secure a permanent move to Parma. Did Milan discard ‘the new Maldini’? No, of course not. But one wonders how Antonelli, who is now at Genoa, would have developed if he had been afforded more time and patience at San Siro.
| GIUSEPPE FAVALLI |
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However, despite endearing himself to the fans with goals in successive games during the 2006-07 campaign, against Messina and Empoli, ‘Favallino’, as he was christened by the Rossoneri faithful, was never really anything more a steady performer at full-back and a useful squad player.
| MATTEO DARMIAN |
 Read more on Darmian |
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But Darmian would not surface in Serie A again until the 2008-09 campaign – and, even then, only as a substitute – and, after spending the following season on loan to Padova, he joined Palermo in a co-ownership deal in 2010. Currently on loan at Torino, it now looks a long way back to San Siro for the now-22-year-old Darmian.
| LEANDRO GRIMI |
 Read more on Grimi |
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He failed to shine at the Artemio Franchi, though, and was sold to Sporting CP in January 2008 after it had become abundantly clear that he was not cut out for Serie A. It became evident that he wasn’t much cut out for the Primeira Liga, either, and he is now on loan at Genk.
| SEASON 2007-08 |
| DIGAO |
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After being recalled in the summer of 2007, Digao made his debut for the club in the Coppa Italia clash with Catania at the tail end of December. His first - and only - appearance in Serie A came later in the season against Lazio when he was brought on at during the interval for the injured Jankulovski. Given he never looked like much of a centre-half, there was little chance of him excelling in an unfamiliar position - and he did not. Digao never played for Milan again and eventually rescinded the final year of his (six-year!) contract with the club in 2010. Shockingly, he is now without a club.
| SEASON 2008-09 |
| GIANLUCA ZAMBROTTA |
 Read more on Zambrotta |
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He remains Milan’s most accomplished left-back, but then that is not saying much. Indeed, while his versatility has often been a major plus for Milan, it is hard not to conclude that the Rossoneri bought a player whose best days were already behind him. His current tally of 80 appearances in just under four seasons does not represent a good return on €10.5m.
| LUCA ANTONINI |
 Read more on Antonini |
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However, if Antonini had excelled, the versatile Zambrotta could have been switched to the right flank. As it was, Ignazio Ibate made the right-back position his own with the kind of consistency and intelligent positional play that were so conspicuous by their absence in Antonini’s performances. Antonini is still at Milan, of course, but it is telling that he was recently linked with a move during the current transfer window.
| SEASON 2009-10 |
| ANDREA DE VITO |
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Leonardo then departed, which proved a disastrous development for De Vito. Indeed, he did not feature once under new boss Massimiliano Allegri during last season's title-winning campaign and the 20-year-old full-back is now out on loan at Cittadella. A spell in Serie B might do him the world of good but it remains to be seen if he has a future at Milan under Allegri.
| SEASON 2010-11 |
| URBY EMANUELSON |
 Read more on Emanuelson |
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In his defence, his versatility has proven something of a hindrance to his attempts to establish himself at Milan because he has never really been afforded a decent run of games at full-back or on the wing. What is bizarre, though, is that, having shown little promise in either position, he has recently been tried out in the trequartista role. The Dutchman still has time to prove himself at San Siro but it now seems highly unlikely that it will be as a left-back.
| DIDAC VILA |
 Read more on Vila |
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However, less than 12 months after his arrival in Italy, he was already on his way back to Espanyol on loan, with Milan having decided after just one appearance in Serie A, against Udinese on the final day of the season, that he was not yet ready for Italian football.
The chances are that his move will become permanent but, in light of his performances in La Liga this season, Milan would be well advised to avoid letting a young full-back of real potential move on without having really given him a proper crack of the whip.
| SEASON 2011-12 |
| TAYE TAIWO |
 Read more on Taiwo |
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Now, though, it looks like a gross error of judgement. Indeed, after making his Serie A debut against Cesena at the tail end of September, the 24-year-old defender featured only three more times in the league as Milan boss Allegri quickly realised that the search for a successor to Maldini’s throne must go on. Over to you, Djamel Mesbah ...
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| Open an account with Sportingbet today and get up to £50 in free bets! |
|
| Sign up with William Hill for a free bet up to £25 |
|
| Sign up with bet365 for a free bet up to £200 |
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| Sign up with Paddy Power - Bet £10, Get £20! |
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