One can only wonder what Cesare Maldini’s hopes were for his boy when he saw him attend his first Milan training session at the age of ten. Perhaps in his wildest dreams his son would emulate him in playing in the famous red and black shirt. He may even have wished for him to win Serie A, which Cesare had done on four occasions with the Rossoneri. Young Paolo would go on to win seven Italian titles in a stellar career which saw him go from Cesare’s boy to being the best defender in the world.
It was a very different Milan that kicked off the 1987/88 Serie A season from the one that would rule Europe just a few seasons later. 1979 was the last title win for the club who had since been demoted after a match fixing scandal and had fought their way back to the top flight. The recently departed Silvio Berlusconi had become the new owner of the club and the summer of 1987 saw the Rossoneri strengthen the existing foundations of what would become one of Europe’s greatest club sides. Arrigo Sacchi came in as manager and amongst the new players arriving at San Siro were Ruud Gullit, Marco van Basten and Carlo Ancelotti.
Paolo Maldini had just turned 19 in the summer of ‘87 and had made his first team debut as a 16-year-old two season earlier. The previous campaign had seen the young left-back establish himself in the side, featuring in all but one of Milan’s league matches. Established Italian internationals Mauro Tassotti and Franco Baresi were regulars in a back four which also featured Filippo Galli. A 20-year-old Alessandro Costacurta made one appearance in the matchday squad that season as he waited in the wings for his opportunity.
The new manager brought a new way of playing which suited Maldini’s athleticism in Sacchi’s more progressive approach. The young full-back was now a vital part of a back four which would be the bedrock of successes to come. His captain Baresi later recalled his early impressions of his young teammate. “He was very young, so I tried to give him some advice. But he needed very little, he was already a great player.”
A full season under his belt and an extra bit of growth in his teenage body had seen Maldini become more athletic both in style and appearance. A left-winger in his earlier days at the club, Maldini moved back into the full-back slot before moving to the first team. An apprenticeship in defence was a real baptism of fire in Italy at the time with some of the world’s best forwards plying their trade in the league.
A young Roberto Baggio was emerging in Florence whilst German international Rudi Voller, World Cup finalist a year earlier, was leading the line for Roma. Juventus had Ian Rush, Sampdoria Gianluca Vialli and Roberto Mancini and then there was the reigning champions Napoli and one Diego Armando Maradona.
Maldini’s campaign began on the sidelines as injury ruled him out of Milan’s first three matches. There were no real signs of a title challenge in those opening three rounds of games as the Rossoneri got off to an indifferent start. A 3-1 win away at Pisa on the opening day was followed by defeat in Florence. A Roberto Baggio-inspired Fiorentina winning 2-0 with the pre-ponytailed divine one grabbing a goal and an assist. A goalless draw with Cesena at San Siro followed as future Milan goalkeeper Sebastiano Rossi kept a clean sheet for the visitors.
It was game number four of the campaign that saw Maldini make his Serie A debut for the campaign. The teenager’s return for a 2-0 home victory over Ascoli set Milan off on a seven-game unbeaten streak in the league during which they only conceded once. The late Gianluca Vialli’s equaliser in a 1-1 draw against Sampdoria in Genoa was the only blemish on the defensive record of Arrigo Sacchi’s men.
It was mid-December by the time Milan lost their second match of the campaign as they were defeated 2-0 by Roma. Maldini had begun to show his value further up the field in the games prior to that defeat as he notched his first assist against Pescara and goal of the season against Avellino.
The defeat to Roma would be the last of Milan’s league campaign as they bounced back from the loss in stunning fashion. A derby victory over Inter the following week set up a five-game winning run that once again featured four clean sheets. The one team to score over those five games was the reigning champions Napoli. An early strike by Brazilian Careca had put the Neapolitans in front only for Milan to firmly confirm their Scudetto credentials by coming back to win 4-1.
If the league table was looking good then the same couldn’t be said of the cup competitions. Milan had already exited the Uefa Cup in the second round at the hands of Spanish side Espanol. Sacchi’s men didn’t fare too well in the Coppa Italia either as 1-0 home defeat to Ascoli would eventually lead to defeat on penalties in the second leg away from home.
Four wins and five draws over the next nine matches kept Milan in the fight for the title as they chased champions Napoli. It was the age of two points for a win in Italy so having that many draws were not as big a setback as it would be now that there is a two-point difference between winning and drawing.
Reward for Maldini’s fine league form came in March of 1988 when he earned the first of what would eventually be a total of 126 international caps. He had already been capped at under-21 level by Maldini Senior when Cesare was in charge of the side. At 19-years-old, Paolo was eight years younger on debut than has father was when he first took to the field for the Azzurri in 1960 at the age of 27.
Yugoslavia were Maldini’s opponents for his international debut as the teenager came up against a side featuring future Milan team-mate Dejan Savicevic. The game was locked at 1-1 when Maldini took to the field as a 53rd-minute substitute. Somewhat fittingly, Italy never conceded again on the night but few watching on would’ve been able to predict that the young debutant would go on to represent his country a further 125 times over the next 14 years.
There was work to be done domestically before the summer tournament could kick off and as Napoli began to falter at the top of the table, Milan faced a daunting run-in to their season end. The Rossoneri were trailing their Neapolitan rivals as the final five fixtures of the campaign loomed. An away trip to the capital to face Roma would be followed by the second derby of the campaign against Inter. That would be followed by what looked to be a title-decider in Naples before the season would with the visit of Juventus to San Siro and an away trip to Como.
Nils Liedholm’s Roma were the first test and they were the last team to beat Milan in Serie A with the dangerous Rudi Voller and Bruno Conti up front. Milan led through a Pietro Paolo Virdis goal in the first half but it was until the 85th minute that they made the game safe. Danielle Massaro, on as a substitute just five minutes earlier, sealing the win.
Inter with Giovanni Trappatoni in charge were the next hurdle and the Nerazzurri were not only looking to derail Milan’s Scudetto hopes, they were looking to avenge a 1-0 defeat earlier in the campaign. Inter, with Guieppe Bergomi, Walter Zenga and Enzo Scifo in their number failed to halt Milan’s charge as goals either side of half-time from Gullit and Virdis and set up a title showdown with Napoli.
Maradona was looking to lead Napoli to a second successive title and despite a poor run of results, victory for the hosts would make them overwhelming favourites to retain their crown. The game didn’t disappoint as a five-goal thriller ensued. Virdis put the visitors ahead before a stunning piece of Maradona free kick brilliance just before half time brought an equaliser. In the second period Virdis’ second of the game and a third by Marco van Basten gave Milan a 3-1 lead before Brazilian Careca headed in to give the Milanisti a nervy end to the game.
That victory gave Milan a one-point lead at the top of the table with just two games remaining but they would end up stumbling over the finish line after winning what everyone thought was the title decider. Two draws in the last two games against Juve and Como could have left the door open for the reigning champions but they couldn’t capitalise.
As Milan and Juve played out a goalless draw at San Siro, Napoli were losing 3-2 to Fiorentina in Florence. That Napoli loss should have taken the pressure off Milan on the final day but they drew again at Como whilst a Gianluca Vialli goal saw Maradona and company lose a third consecutive game as they threw away a chance at back-to-back championships.
It had been a momentous season for Maldini and whilst the previous term would be seen as his ‘breakthrough’ campaign, 1987/88 was his true arrival. The first of 26 major trophies including another six to add to the 87/88 win. The following campaign would see him lift the European Cup on the first of five occasions. The season ended at Euro 88 where Maldini would play in all four of Italy’s matches in what would be the first of his seven major tournament appearances, four World Cups and three European Championships.
Picking a single season out from a true legend of calcio and perhaps the greatest defender ever to have played the beautiful game is not easy, but 1987/88 is the first time the world took note of Paolo Maldini: auguri, maestro on today, your 55th birthday.