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Featured Image Credit: YouTube/Blitz Soccer Academy
Maldini, nicknamed 'Il Capitano' by many, would go on to play 902 club games for the Italian giants, winning 126 Italy caps and 26 trophies in a glorious period of success.
As well as spearheading the club to soaring heights - so much so that Milan retired the number three shirt in his honour - the centre-back taught millions around the world the art of defending in its purest form.
"If I have to make a tackle then I have already made a mistake."
Maldini, one of only 18 players to have made over 1,000 career appearances, lifted five Champions League trophies, seven Serie A titles, one Coppa Italia and five Supercoppa Italiana titles in his career.
He also won five European Super Cups, two Intercontinental trophies and a FIFA World Cup in that time.
His presence lifted the club to unprecedented heights during his stay at the San Siro and in 2007, Maldini became the oldest player to captain a Champions League winning side at 37 years of age.
Nobody even comes close.
The Italian defender was a striker's worst nightmare and a defender's dream.
"A real monster." Marcel Desailly once said of Maldini. "I find it incredible he has never been World or European Footballer of the Year. Alongside Franco Baresi he was the best defender I've ever seen in my career.
"Although everybody tends to think of him just as a full-back, he could also play as a stopper.
"Most people remember that great Milan side of the late-80s for its attacking play and for the forward pair of Ruud Gullit and Marco van Basten, but it was a team built on a very solid defence, and Maldini was the cornerstone."
To celebrate the anniversary of his AC Milan debut, here is a compilation of Maldini in his prime.
Playing with the likes of Baresi, Seedorf, Romario and Filippo Inzaghi, the Italian produced some of the finest tackles and defensive moments in football history.
Sit back, relax and witness one of the all-time greats doing what he did best.
His legacy will live on forever and, while these clips will circulate on a yearly basis, we thought we'd just remind you of his unbelievable talent.