This time around, the former Ballon D'Or winner comes back to the club where he made his name after failing to become an integral part of Real Madrid's starting XI.
Although some of the more passionate Rossoneri fans are blinded by their undying love for the Brazilian, there are a few who realize that this nostalgic move was hardly the right one to spearhead Milan towards their objectives.
The irony is that Adriano Galliani has urged for the past few seasons that the best way to bring Milan to the top again is by building from the youth academy. Long gone are the days when President Silvio Berlusconi could spend lavishly for a plethora of super stars.
Now, the money being spent by the likes of Manchester City, Paris St. Germain, and Monaco is far too much for Milan to compete with.
Without further ado, let's take a look at some of the positives and negatives of the Kaka to Milan swoop.
Even if his play on the field isn't up to the same level, Kaka's star still shines brightly throughout the world. He is not only one of the most followed people on Twitter, but one of the most recognizable faces in sports.
Kaka's move in a marketing sense could be viewed as a positive, as the team will sell plenty of No. 22 jerseys.
Kaka's can be a youth mentor even if he isn't playing. Riccardo Saponara, the youngster purchased from Serie B side Empoli, has been compared to Kaka for his long strides, creativity, and finishing from distance.
His experience could definitely prove vital in tense moments down the stretch. He has shown in bursts that he still has that fantastic finishing ability from outside the area and can set up teammates.
Even though Kaka arrived on a free transfer, Milan still have to pay his exorbitant salary, which is still among the highest on the team despite the player slashing it by around 50 percent.
Funnily enough, he has refused to earn money until he recoups from the injury picked up against Torino, which will put him out of action for the next month.
Kaka's inclusion in the team means there's probably a youngster who will be kept out of action. At 31 years of age, you must figure that the Brazilian still has two seasons he can give at a high level, assuming he can stay fit.
It doesn't make sense that a team that claims to be developing from the ground up would keep some of their most promising young players out of the starting lineup where they could be gaining valuable experience and building chemistry with teammates.
Even though Kaka personifies the ideals that Milan strives to represent, his value off the pitch will most likely be greater than what he does on it.