Through the past decade, Milan has made signings which have spearheaded the squad to the upper echelons of European football.
Since 2003, the Rossoneri went to an impressive three Champions League finals and won two of them. Behind those golden years were some of the best signings we've seen, including bargain bin steals and savvy scouting jewels.
Here's a list of the five shrewdest signings Milan have in recent times:
The Ukrainian rifleman formerly of Dynamo Kiev joined Milan in 1999.
While many were curious about how his talent would translate to Italy, no one could have ever imagined the impact he'd have on the team, rewriting the history books as one of the main catalysts to their success during his first tenure.
Shevchenko won the Ballon D'Or and scored the decisive penalty in the 2003 Champions League final against Juventus.
Despite an embarrassing comeback attempt with the Rossoneri after his failed stint with Chelsea, Shevchenko reached immortality status among fans with the contributions he gave them during his golden years.
Gennaro Ringhio Gattuso was a staple of Milan's midfield for more than a decade, where he patrolled the midfield and became the enforcer in front of the defense.
His no nonsense style, tenacity and work-rate made him a favorite among the Curva Sud faithful. Apart from being an iconic Milan player, he also carved himself a major role on the Italian national team and was a pillar in the 2006 World Cup winning side.
Milan signed Kaka in 2003 for the measly sum of €8.5m from Brazilian giants Sao Paulo. The then 21-year-old would have an instant impact with the club, changing the definition of what Italians had considered to be the trequartista position.
Long gone were the days of the slow-footed, low-socked attacking midfielder that we were used to seeing as Kaka revolutionized the position at Milan with his searing pace when in possession of the ball.
His long strides saw him effortlessly glide past on rushing defenders, and he'd then use his vision or touch to set up a teammate or put a beautiful curler past the goalkeeper.
Kaka is the main reason why Milan won the 2007 Champions League final against Liverpool
Possibly the greatest deep-lying play-maker of this generation and a humble leader who has always played the game the right away.
Even though he had a somewhat bitter divorce from the Rossoneri, it's impossible to ignore the value he had for Milan through the years.
Pirlo was the creative force in the midfield for a team that reached three Champions League finals and an Italian side that won the World Cup. You'd be hard-pressed to find many players with such an impressive resume.
What Pirlo did on the field was nothing short of genius.
His vision with the ball at his feet was extraordinary, as well as his perfectly placed free kicks which so often would give a big problem to the opposing goalkeeper.
Filippo Inzaghi was signed from Juventus in 2001 and spent more than a decade with the club that he is now currently employed at as their youth coach.
During his spell with the Rossoneri, Inzaghi became one of the most feared European goalscorers, always putting himself in the right place at the right time.
He was never blessed with technique or pace, so he used his uncanny sense of positioning to score poacher goals and always delivered on the biggest stage.
It was his brace against Liverpool in the 2007 Champions League final which sealed the win and gave the team their seventh cup in the historic competition.