AC Milan is one of the most storied clubs in footballing history, having spent all but two seasons in Serie A since its foundation.
In Italy alone, we are tied with rivals Inter for the second-most Scudettos won with 19. Internationally, the Rossoneri hold the most prestige, having accumulated a mammoth 18 FIFA and UEFA trophies – the highest tally of any Italian side.
Our most successful period – aside from a stint of four Serie A titles in the 1950s – is undoubtedly the Silvio Berlusconi era between the mid-’80s and early 2010s, where Milan boasted some of the world’s most talented players.
As a result, many of those stars won a plethora of trophies for the club. It is well documented that defensive stalwart Paolo Maldini holds the record with 26 honors to his name, but who are the players next in line in their respective trophy hauls? With that in mind, here are the most decorated footballers in Milan’s history behind Maldini.
= 3. Filippo Galli (17 trophies)
Monza-born defender Filippo Galli came through Milan’s youth ranks in the early 1980s before being sent on a year-long loan to Pescara for the 1982-83 season. Galli eventually made his first-team debut with the Rossoneri in September 1983, after which point he made a staggering 325 appearances for the club, spanning a 13-year career. The defender was part of two iconic Milan teams of that era, including Arrigo Sacchi’s ‘The Immortals’ between 1988-90, who were one of the few teams to successfully defend their European crown, and since then only Real Madrid has been able to defend their crown successfully.
Then, with Fabio Capello from 1991, Galli and Milan won three consecutive Serie A titles between 1992 and 1994, racking up a 58-match unbeaten run and thus earning their nickname ‘The Invincibles’. While Galli eventually lost his place to Alessandro Costacurta from 1988-89, the defender did make some notable contributions. He was part of the Milan side who conceded just 12 goals in 30 league games in 1987-88 and helped defeat Barcelona 4-0 in the 1994 Champions League final, one of the most dominant performances in Europe’s elite competition to date. Galli left Milan for Reggiana in 1996 with five Serie A, four Supercoppa Italiana, and three Champions League titles to his name among 17 total trophies won with the club.
= 3. Mauro Tassotti (17 trophies)
Winning the exact combination of trophies as Galli – which also consisted of three European Super Cups and two Intercontinental Cups – Mauro Tassotti actually spent two seasons at Lazio before joining Milan in 1980. His career with the Rossoneri had humble beginnings, as he only switched allegiances following the two clubs’ involvement in the match-fixing scandal and subsequent relegation to Serie B in 1980. In fact, Tassotti would be one of the few players who was with Milan during both campaigns in Italy’s second tier, although he emerged as one of the few stars in an otherwise bleak period for the club.
Tassotti, who was often deployed as a right-back but occasionally filled in in the center, cemented his place in the Milan side during both the Sacchi and Capello eras, forming part of a defense that is largely considered one of the greatest of all time. Sacchi appointed the defender as vice-captain after stalwart Franco Baresi as he helped Milan not only win 17 trophies but also post the best defensive records in Serie A. These included the aforementioned 1987-88 season as well as the 1993-94 campaign, where Milan conceded just 15 goals. Tassotti retired alongside Baresi in 1997 having made 581 appearances for the Rossoneri, scoring 10 times and providing 34 assists.
= 2. Roberto Donadoni (18 trophies)
Despite becoming a Milan legend by the end of his career, Roberto Donadoni made 120 appearances for Atalanta before becoming a Rossonero in 1986. Usually deployed in a wide-right midfield role, Donadoni also featured heavily under both Sacchi and Capello in their trophy-laden eras, although his main contributions came through assisting goals rather than scoring. He set up Ruud Gullit in their 4-0 romp of Steaua Bucuresti in the 1989 European Cup and did the same for Daniele Massaro in Milan’s thrashing of Barcelona by the same scoreline in the 1994 Champions League final.
In his two stints at the club between 1986-1996 and 1997-1999, Donadoni laid on 60 assists for his teammates alongside an impressive return of 23 goals. In between those tenures, though, the wide midfielder became one of the pioneers of Major League Soccer. Donadoni joined the NY/NJ MetroStars in 1996 alongside USMNT stars Tab Ramos and Tony Meola. Despite a slow start to life in MLS, the MetroStars employed one of soccer better strategies in merging with the Austrian energy drink conglomerate in 2006 to become the New York Red Bulls, which has since won them three Supporters’ Shields. Donadoni, meanwhile, returned to Milan in 1997 to win his sixth Serie A title, taking his tally up to 18 trophies to go alongside an impressive 390 appearances for the Rossoneri.
= 2. Franco Baresi (18 trophies)
So often Maldini’s defensive partner during his staggering 20-year career at Milan, Franco Baresi is widely regarded as one of the greatest defenders in footballing history. Of the names on this list, Baresi’s career spans the furthest back, having started out with the club in 1972, who he chose after being rejected by rivals Inter in favor of brother Guiseppe. Playing either as a sweeper or center-back, Baresi cemented his place in the Milan starting eleven in 1978-79 alongside future tactician Fabio Capello, where the club went on to win its 10th Serie A title – a trophy which takes his tally above the likes of Galli and Tassotti.
After that point, though, came the aforementioned dark periods of the Rossoneri’s history, throughout which Baresi elected to stay with the club despite being a member of Italy’s 1982 World Cup-winning team. That same year, at just 22 years old, the defender’s loyalty and performances were rewarded with the captaincy following the departures of Aldo Maldera and Fulvio Collovati. From that point onwards, Baresi became synonymous with Milan and an iconic symbol of the aforementioned all-Italian defense that proved unbeatable under Sacchi and Capello. Aged 37, Baresi hung up his boots with a staggering 716 appearances to his name, in which time he scored 33 goals and provided 24 assists from deep.
1. Alessandro Costacurta (23 trophies)
Way ahead of the previous four entries is center-back Alessandro Costacurta, who went on to win a mammoth 23 trophies during his time at Milan. Costacurta holds the third most official appearances for the club (behind Baresi and Maldini) having made a staggering 663 appearances for the Rossoneri, His one-club career spans all the way back to 1979, before eventually making his first team debut in October 1987 following a year-long loan at Monza. As mentioned earlier, Costacurta took over from the experienced Galli from the 1988-89 campaign onwards, where he too featured in the club’s trophy-laden eras.
Following Baresi and Tassotti’s retirement in 1997, Costacurta was named vice-captain behind Maldini and experienced several trophy droughts after the departure of such key players and managers. Aside from Milan’s 1998-99 victory – for which Donadoni was also present – the Rossoneri endured a number of trophyless campaigns before Carlo Ancelotti took the side back to the Italian and European summits starting in the 2002-03 season. Two Champions League trophies at the turn of the century – as well as the one that got away in Istanbul – joined a 17th club Scudetto alongside the Supercoppa Italiana and the club’s first Coppa Italia since 1977. This took Costacurta’s tally to 24 trophies with Milan – just two behind Maldini – before retiring in 2007 aged 41.
Paolo Maldini’s record of seven Serie A titles, five European titles, one Coppa Italia, five Super Coppa Italia, four European Super Cups, and three Intercontinental Cups will take some beating.
Even with son Daniel continuing in his footsteps – despite being currently on loan at Spezia – Milan will likely never experience another golden era quite like those under Berlusconi, at least not for some time.
For that reason, then, it is vital not only to laud the legend of Maldini but also those that preceded, succeeded, and played alongside him, who themselves racked up a staggering tally of trophies that almost all world players would be proud of.
