The last time in recent Milan history that the Rossoneri were close to having brothers playing at the same time was when Digao (Kaka‘s brother) was asked to join the team. It was, however, without success. Every now and then a star player is given the opportunity to have one of their family members join, but it almost always ends up with questionable results. Although uncertain why this is done, it is perhaps in the hopes of having to benefit from a player with the same upbringing and therefore the potential of having 2 star players.
Either way, the first time this happened for the Rossoneri, was when the brother of a famous football player joined during their 1954/55 season. It was Karl, brother of Nils Liedholm (from the highly skilled Gre-No-Li Trio), who at the time was placed only for friendly matches to see if he had any potential living up to the Liedholm name. The unfortunate situation was that he did not impress Rizzoli and his advisors. Karl had played one official league game on October 13th, 1954, against Reggina. The event ended with a more than favorable 8-1 win for Milan, where the young Karl was added onto the pitch in the second half, in place of Schiaffino. But by then there wasn’t much left to do to impress, since the Rossoneri were already well placed in the lead.