AC Milan pulled off a major coup when they signed Andrea Pirlo from rivals Inter in June 2001. His arrival marked the start of a new era for the Rossoneri, who had just brought in Carlo Ancelotti to replace Fatih Terim as manager.
Ancelotti understood Pirlo’s vast potential, so he decided to build the team around this cultured young playmaker. Pirlo has struggled to make an impact at Inter, but excelled on the other half of the Milan divide.
Originally an advanced midfielder, Ancelotti saw a new vision for Pirlo as the Rossoneri’s regista. However, he was also wise enough to determine that Pirlo would only flourish if someone could do the dirty work alongside him.
🇮🇹 Andrea Pirlo was simply stunning.#UCL pic.twitter.com/S8pa6SCy80
— UEFA Champions League (@ChampionsLeague) May 19, 2022
As such, Ancelotti paired Pirlo with the combative Gennaro Gattuso in the middle of the park – and the rest is history. Pirlo and Gattuso offered an irresistible blend of steel and flair, turning Milan into one of the most successful teams in Europe during the noughties. They also reprised their partnership for the national team, powering Italy to victory in the 2006 World Cup.
The Perfect Contrast
Gattuso and Pirlo were like chalk and cheese, yet they complemented one another perfectly.
Gattuso was the warrior – relentless, aggressive and tireless in his pressing, snapping at the heels of opponents like an enraged terrier.
He thrived on breaking up opposition attacks, throwing himself into tackles and disrupting play with his sheer tenacity. What he lacked in technical finesse, he more than made up for with his work ethic and tactical discipline.
No way through 🚫
🔴⚫️ Two-time winner Gennaro Gattuso worked tirelessly behind the scenes 💪#UCL | @acmilan pic.twitter.com/GKCRTRc1kY
— UEFA Champions League (@ChampionsLeague) July 13, 2020
By contrast, Pirlo was the artist. His ability to dictate the tempo of a game with his range of
passing and vision was second to none. While Gattuso fought battles in the trenches, Pirlo
orchestrated play with effortless composure and precision. Ancelotti’s redeployment of him as a deep lying playmaker allowed Milan to control games, shifting between short, incisive passes and long, raking balls that unlocked defences.
Together, they formed the perfect yin and yang, a combination of brute force and elegance that made Milan’s midfield one of the best in world football.
Defensive Rocks: Paolo Maldini – Milan’s Il Capitano
Dominating European Football
In their second season, Pirlo and Gattuso helped AC Milan win the Champions League. The
Rossoneri beat Inter and Juventus en route to that famous triumph. After a goalless final at Old Trafford, Milan beat Juventus in a shootout to win the first all-Italian decider.
A year later, Scudetto success was celebrated as the dynamic duo won Serie A title for the first time in 2004. An emerging Kaka thrived in the No.10 role and Andriy Shevchenko – who claimed the 2004 Ballon d’Or led the line with aplomb. Further back, a formidable defence featuring Paolo Maldini, Cafu, Alessandro Nesta and Alessandro Costacurta stood out.
For all that elite talent, Milan’s greatest strength was in midfield. Pirlo and Gattuso linked up with the majestic Clarence Seedorf as the Rossoneri finished 11 points clear of nearest rivals Roma.
Ancelotti’s side suffered just two league defeats, one of which came with the title wrapped up. Such was their dominance, Milan could afford to ease up in the last five games of the campaign. Shevchenko’s winner against title rivals Roma secured the Scudetto with two games to spare.
AC Milan reached another Champions League final in 2005, but they blew a 3-0 lead and lost to Liverpool on penalties. It was an especially brutal blow for Pirlo, who missed his spot-kick during the shootout.
However, Milan gained sweet revenge in 2007. They faced Liverpool in another Champions
League final, and this time they were not to be denied. Pirlo’s free-kick deflected in off Filippo Inzaghi to open the scoring, and the Italian striker sealed a 2-1 victory by scoring in the 83rd minute.
This game was arguably the apex of the Pirlo-Gattuso partnership. They went up against a star-studded midfield featuring Xabi Alonso, Javier Mascherano and Steven Gerrard, and they came out on top.
Gattuso’s relentless pressing and defensive acumen allowed Pirlo to dictate play from deep. It was the ultimate demonstration of their complementary skills, showcasing why they were the heartbeat of that legendary Milan side.
Midfield Magicians: A bona fide winner who simply oozed class, Clarence Seedorf
Longevity and Legacy
Their partnership extended beyond AC Milan. Most notably, they started at the heart of Italy’s midfield in the 2006 World Cup final. The Azzurri were underdogs against an elite France team, which featured Patrick Vieira, Claude Makelele and Zinedine Zidane in midfield.
However, the trusty Pirlo-Gattuso axis proved decisive once again, as Italy defied the odds and ultimately won on penalties. Pirlo scored the first goal of the shootout, exorcising the demons of his miss in the 2005 Champions League final.
Ancelotti left AC Milan in 2009, but Pirlo stayed for another two years. The Rossoneri won
another Serie A title in 2011. At that point, the club deemed that Pirlo was on the decline. Milan failed to renew his contract and the midfielder joined Juventus on a free transfer.
It proved to be a major miscalculation from Milan, as Pirlo thrived in Turin. He was named Serie A Footballer of the Year in each of his first three seasons with the Old Lady and helped Juve to four consecutive titles.
Gattuso left in 2012, having made 468 appearances in 13 years at the club. He spent a season in Switzerland before retiring, while Pirlo’s career ended with a stint at New York City FC.
Both men have landed big managerial jobs since hanging up their boots, but they’ve struggled to replicate the success they enjoyed during their playing careers.
Their legacy is truly defined by their time spent together at Milan. They embodied everything great about Italian football – tactical intelligence, resilience and artistry. Their understanding of each other’s strengths created a dynamic midfield partnership that remains one of the most iconic duos in history.
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