The trend looks set to continue after Daniel Maldini, son of Rossoneri great Paolo, made his first team debut for the club in a pre-season friendly defeat by Bayern Munich on Tuesday.
The youngster came on as a substitute late in the second half as Marco Giampaolo’s side were undone by a late first half strike from Leon Goretzka in Kansas City.
Unlike his father Paolo and his late grandfather Cesare, who were both defenders for the club, young prodigy Daniel is tricky winger who is highly regarded by the Milan hierarchy.
He earned his first call up to the Italy Under-18 team this season after scoring nine goals from 22 appearances for Milan Primavera.
His older brother Christian also came through the youth ranks at the San Siro, but he failed to make a first team appearance and currently plays for Serie C side Fano.
— AC Milan (@acmilan) July 24, 2019
Daniel looks set to have a better chance than his brother of maintaining the family dynasty at Milan, but he has big boots to fill should he seek to emulate his forefather’s feats.
Grandfather Cesare, who like his son also captained the side, joined Milan in 1954 and made 412 appearances for the club in all competitions, winning four Serie A titles and the European Cup in 1962.
He also coached the team twice. He won the Copa Italia and the European Cup Winners’ Cup as manager during his tenure from 1972 until 1974, before taking the reins again in 2001.
By this point, his son Paolo was already regarded as one of the club’s greatest players – a status he would go on to cement.
Paolo, who is now the club’s technical director, won an impressive 26 trophies during his time at the club, including five Champions League titles, seven Serie A titles and one Coppa Italia.
He made 901 official appearances before retiring aged 41. The club retired his No 3 shirt shortly afterwards, although Daniel would be able to wear it, should he choose to.
20th January 1985: Paolo Maldini makes his AC Milan first team debut at age 16.
*34 years later*
23rd July 2019: Daniel Maldini makes his AC Milan first team debut at age 17.
The Maldini legacy continues. pic.twitter.com/lAlOflsMez
— Squawka News (@SquawkaNews) July 24, 2019
The youngest Maldini was unable to prevent his side from suffering defeat by the German champions in their International Champions Cup clash.
Right back Joshua Kimmich found Goretzka with a defence-splitting pass deep into stoppage time in the first period and the German internatioanl coolly slotted the ball past Gianluigi Donnarumma to give the club a second win in the exhibition competition.
Milan had their chances in the second half, not least when Patrick Cutrone was put through one-on-one with Sven Ulreich only to be denied by the goalkeeper, but could not find an equaliser on a warm night in Kansas City.
The match was Milan’s first since head coach Marco Giampaolo took the helm at the Serie A club, who parted ways with Gennaro Gattuso at the end of last season.
Next up for Bayern Munich is a semi-final clash with Turkey’s Fenerbahce on Tuesday while Milan face Portuguese outfit Benfica on Sunday.