The Greatest Left-Back of All Time

AC Milan chants echoed through San Siro stadium on a chilly evening in 2005, as their team hosted relegation-threatened side Reggina FC in a mid-autumn league game. The clock hit the fifth minute when Milan left-back Paolo Maldini received a pass outside of the box, shrugged off one defender, and buried the ball in the back of the net with a sharp shot. It was just the start Milan needed, taking an early 1-0 lead courtesy of Paolo Maldini. Just 15 minutes later, Milan won a corner. Rui Costa whipped the ball into the box, and a towering header from Maldini made the score 2-0. The stadium was buzzing with excitement as the home team settled the match, ending 2-1. This would be Paolo Maldini’s only brace during his professional playing career. His defensive prowess, leadership, and consistent performances have impressed many across generations, and he is widely considered to be the greatest left-back of all time.

Born in Milan in 1968, Paolo Maldini had his heart set on following his passion for soccer from an early age. The Maldini heritage was always strongly centered around AC Milan, so his family’s history with the club laid the groundwork for Paolo Maldini’s love for the team. The most influential figure in the young Italian’s early life was his father, Cesare Maldini, an AC Milan icon who spent 12 seasons with the club during his professional career. This loyalty earned him the honor of being a one-club legend, and his son would soon follow in his footsteps.

Paolo Maldini joined Milan’s youth team when he was just 16 and made his professional debut during the 1984-1985 season. At 17, he was promoted to the starting 11 and donned the number three, the same number his dad wore. Paolo Maldini started off by playing as a right-back because he was right footed, but his two-footed versatility soon allowed him to play on the left, where he was more comfortable. Under the mentorship of experienced, dependable Milan captain and center-back Franco Baresi, Paolo Maldini became a staple in the Milan backline due to his fiery fighting spirit, ball-winning abilities, and defensive awareness. The Italian was feared by opponent attackers for his iconic sliding tackle. Whenever an attacker dribbled at Paolo Maldini, he would jump in fearlessly, gliding across the grass to whisk the ball away or clear it up the field, often leaving his opponents on the ground wondering what just happened.

Though primarily a left-back, Paolo Maldini’s flexibility allowed him to be deployed anywhere across the defense. Out of the 193 total games where Paolo Maldini partnered Baresi in the center of the defense, the two performed brilliantly together, conceding only 23 goals in all. The pair was part of what is often considered to be history’s greatest back four: Paolo Maldini, Baresi, Alessandro Costacurta, and Mauro Tassotti. Baresi and Costacurta, the two disciplined and hard-working center-backs, were flanked by an experienced Tassotti on the right and a young, dependable Paolo Maldini on the left. The backline played in the Catenaccio system, a unique Italian style of defending with a very strong emphasis on defensive shape and shutting down threats. Together, the back four could coordinate incredibly well to nullify opponent attackers and instilled fear in the minds of their opponents. Milan’s defense became so rigid and reliable that the team won the 1987-1988 league title with only two losses. The next season, the squad secured their consecutive Serie A title, this time going undefeated the entire season and earning the nickname “The Invincibles.” The same four defenders played together for the national team as well. One of their best performances was during the 1990 World Cup, where despite placing third in the tournament, the backline, having conceded just two goals throughout the competition, earned Italy the title of best defense. Later, after Baresi’s retirement, Paolo Maldini’s vocal leadership and inspirational spirit earned him the mantle of captainship for both AC Milan and the national squad, with fans nicknaming him “Il Capitano,” Italian for “The Captain.”

During his peak, two of the best clubs in the world, Manchester United and Real Madrid, attempted to secure the left-back’s signature. However, Il Capitano refused both offers despite the glory and riches, standing by his undying love for Milan. His longevity allowed him to play a total of 25 seasons with the Italian giants, winning 26 trophies, including seven league titles, five European Cups, and four UEFA Super Cups, until his eventual retirement at the astonishing age of 41 in 2009. Paolo Maldini’s loyalty and breathtaking performances for Milan didn’t go unnoticed, attracting attention from the Italian National Team. He was called up on multiple occasions, and his execution was equally impressive when he represented his country on the big stage. Il Capitano and Italy certainly reached great heights together, making it all the way to the 1994 World Cup final, where they narrowly lost on penalties to Brazil. Unfortunately, Paolo Maldini retired from international soccer at the age of 34, going trophy-less during his tenure with the national squad. Still, his superb longevity made him Italy’s most capped player at the time, a record later broken by Fabio Cannavaro and Gianluigi Buffon. To respect Paolo Maldini’s legacy at AC Milan, the club decided to retire the number three.

The epitome of a one-club legend, Paolo Maldini proved his undying devotion to Milan even after retirement, continuing to serve the club as technical director. Speaking in an online interview a few years ago, Paolo Maldini branded himself as “the biggest loser in history,” regretting the 1994 World Cup final loss as well as three European Cup final losses during his career. Nevertheless, his presence on the field revolutionized the role of the left-back with his intense aggression, physicality, leadership, and accurate judgment on the field. He became the perfect example of a complete defender and a figure who young, rising stars could look up to for generations to come.