“My grandfather is Milan, my father is Milan, I’m Milan and my son is Milan. Forget it”.

And that was that. The mere suggestion that his son could one day ply his trade somewhere other than Milan was so scandalous, that even Sir Alex Ferguson could not escape Cesare Maldini’s disdain. The great Scot wasn’t the first to court Paolo, and he wasn’t going to be the last. But even when his father wasn’t speaking for him, the answer was always going to be the same – Maldini and Milan are inseparable, you can’t have one without the other.

Italian football is synonymous with the one-club man, but Paolo Maldini’s lasting influence as the bandiera of his family name takes his legend a step further. No one has found themselves woven into the fabric of a footballing institution quite like Milan’s captain of 12 years.

Rite of Passage

It was clear, even with his career in its infancy, that Paolo Maldini was being groomed to take over the armband at Milan. At Milanello, his father’s name plastered on the walls everywhere you went – with over 400 appearances, 4 Scudetti and the distinction of being the captain that led the club to its first-ever European Cup to his name, “Cesarone” was as legendary as they came. To be able to live up to, nay, surpass his father’s gargantuan achievements made Maldini a natural choice when he became club captain in 1997.

Having already led the team out many times before in the absence of Franco Baresi and Mauro Tassotti, Maldini’s captaincy began under a cloud of strife. The departures of the aforementioned Baresi and Tassotti had left a gaping void in the heart of the defence as well as the dressing room and having to fill both immediately put Maldini’s leadership skills to the test.

Without many of the stars of the trophy-laden ‘Invincibles’ era, Maldini’s first side as Milan captain was one very much on the decline. Milan was at the heart of the Calcio’s supremacy in the 90s, but was ending the decade with a whimper. This is what made their final day triumph over Lazio to secure the 1998/99 Serie A title so surprising – after all, this was the side that finished 11th and 10th in the previous two seasons.

It was a Scudetto triumph that no one had expected. “Perhaps not even ourselves,” Maldini admitted. “At the players’ technical level, we were not a strong squad like several of the other teams – but we found something that made it.” That something turned out to be his immense ability to rally the troops in what were otherwise tough times for the Lombardy giants.

An Unhappy Marriage

Even with the title parade in full swing at the Piazzale Angelo Moratti, there was trouble brewing behind the scenes.

Milanisti are, like most fan bases around Italy, ferociously passionate and outspoken, none more so than the ultras. Taking up their station in the San Siro’s curva sud (south stand), they brandish their banners, unfurl giant tifos, belt out chants and just generally create a nuisance to suffocate opponents over the 90 minutes of their visit.

They also control the narrative of fan opinion, making them a powerful ally to have on your side. Unfortunately for Maldini, that was never the case. It was he who called out the ultras for showing their discontent when they pelted the pitch with objects in a match against Parma amidst the terrible 1997/98 campaign, resulting in the match getting suspended.

The following year, with the title sealed on the final day, Maldini headed straight for the tunnel at full-time with Alessandro Costacurta, rather than staying out and celebrating with the fans, another sign of how far the ties between factions of the Rossoneri faithful and their captain had severed.

Leading the Renaissance

The hangover of the limp late 90s years spilled over into the new millennium. 2001 was particularly tumultuous, with Alberto Zaccheroni, Cesare Maldini, Fatih Terim and Mauro Tassotti serving as managers between March and November. It was only when Carlo Ancelotti, one of the first marquee player signings of the Silvio Berlusconi era, was brought back in a managerial capacity, did light emerge at the end of the tunnel.

After a first season which he used to steady the ship, securing the club’s return to the Champions League, Ancelotti sought to build a spine around which the team could revolve. Milan and Berlusconi flexed their financial muscle once again, raiding rivals Lazio and Inter for Alessandro Nesta and Clarence Seedorf respectively.

Ancelotti, who was one of the first signings made by Arrigo Sacchi to re-establish Milan’s dominance in the 80s, borrowed more than a few tricks from his legendary mentor’s playbook, chief among which was the notoriously narrow 4-3-1-2 formation.

With the huge demands that Ancelotti’s system put on full-backs, Maldini found his role being redefined. His advancing years made him a better fit to assume the role of centre-half at times, where his unparalleled defensive intelligence meant he rarely had to make tackles. The combative, hard as nails Nesta was the perfect foil as their side went on to win the first all-Italian Champions League final over Juventus in one of the more drab showpiece occasions in the competition’s history. Not that Maldini cared – 40 years to the day Cesare lifted Milan’s first-ever European Cup as captain, his son had emulated the feat.

Istanbul and Athens

“It reminds me of how strange football can be.”

Looking back at a match that got off to a dream start only to descend into a nightmare, Maldini speaks about the infamous 2005 Champions League final in hushed undertones, even to this day. For the man who won everything, and then did it again, being captain of the side that suffered one of football’s greatest capitulations will forever be a blemish on an otherwise spotless record.

By the time they returned to the Champions League final in 2005, Ancelotti’s Milan had wrestled back their stranglehold over Italian football. They had won the Coppa Italia, Maldini’s first and only cup win, and the Scudetto in the space of 12 months. The formidable side that won over Juventus at Old Trafford was joined by the likes of Hernán Crespo, Cafu, Kaká and Jaap Stam, making them overwhelming favourites over a Liverpool side that had struggled domestically that season.

Maldini’s smart volleyed finish put the diavolo ahead inside a minute and made him the oldest and quickest player to score in a Champions League final. It seemed as if everyone was sticking to the script, but it just wasn’t to be.

Mulling retirement at that point, the defeat is probably what spurred Maldini on to keep going. His desire to have another crack at putting things right came two years later in Athens, and as fate would have it, Liverpool lined up on the other side once again.

Ancelotti learned from his mistakes and shored up the midfield that was so hopelessly overrun in the second half in Istanbul by picking Massimo Ambrosini, who had put in a series of top performances on the road to the final. Ambrosini’s consistency in the middle of the park and Kaká’s irresistible form meant that Ancelotti, notorious for tactical rigidity, ditched his 4-3-1-2 for a 4-3-2-1, otherwise known as the famed ‘Christmas Tree’ formation.

With a 2-1 win on the night and an incredible fifth Champions League trophy in his arms, Maldini could rest easy knowing he had ended a storied career playing in Europe’s premier club competition as perhaps its greatest winner.

A Bitter End

That night in Athens marked the beginning of the end. Although he planned to stay on for one more year, Maldini later extended his contract till the end of the 2008/09 season. The final campaign started poorly, but the Rossoneri picked themselves up in time for the Derby di Milano. Maldini led a resolute defensive performance in a match which was settled by Ronaldinho’s goal to make it three wins in a row. However, Jose Mourinho’s Inter recovered handsomely from this early setback and sauntered to the title, 10 points clear of their neighbours.

Off the field, things went from bad to worse, with the upstairs board met with Milanisti fury over the state of affairs. It looked as if the piling debt would force Berlusconi’s hand, as Kaká came close to moving in that season’s January transfer window to football’s nouveau riche at the time, Manchester City. While the move eventually collapsed, the fans were seriously irked by Berlusconi and his right-hand man, Adriano Galliani.

Maldini’s attempts to build bridges as club captain saw his stock further plummet with the supporters, to the point that his farewell match at the San Siro descended into a farce.

What should have been a celebration of a glittering 25-year career was marred by a hostile atmosphere created by the ultras. Tifos so big you could’ve seen them from the Duomo di Milano were unveiled in the curva sud, “For your 25 years of glorious service you have the thanks of those who you called mercenaries and misers,” in reference to the time when Maldini allegedly called the ultras ‘mercenaries’ when the two met at the Milan airport in the aftermath of Istanbul.

Throughout the game, songs hailing Franco Baresi as the ‘true’ captain were sung in unison. With tears in his eyes and jeers ringing in his ears, Paolo Maldini thus exited the San Siro as a player for the last time.

Back Where It Began

As his father once said, “Maldini’s soul belongs to Milan”. It was hard to keep him away for long, and when Berlusconi’s reign finally ended in 2017, the opportunity to return to the club under the new regime in the capacity of Sporting Director presented itself, which the great man took, no questions asked.

As has been the case many times before, Milan looks to Maldini to once again lead them out of crisis. Three decades or so of experience suggests that there is no man better for this task than their captain of captains.

Written by Kabir Ali

El Arte Del Futbol is an official content creator for OneFootball. Find more original features, Player Profiles and tactical analysis on www.elartedf.com. If you are reading this on our website, we’d like to thank you for your continuous support!