It is not uncommon for former players to turn their hand to managerial life. For many, the
transition doesn’t come all that easily. It is a completely different level of pressure compared
to being a member of a team on the pitch.
There is no hiding place for the head coach of a football team, as it is where the buck stops.
The latest websites about football are rife with managerial job speculation, and it’s an area
of massive interest among fans.
Current AC Milan head coach Stefano Pioli was a former player, with the bulk of his playing
days at Fiorentina, which was, incidentally, the last club he managed before joining AC
Milan.
As Milan manager, he delivered a Serie A title in 2021-22, Pioli was never an AC Milan
player. Here is a look at some prominent former players who tried their hand at managing
the great club.
Fabio Capello
Capello is one of the greatest examples of a former player turned managerial hero. Fabio
Capello spent four seasons as a player with AC Milan, one of which saw the midfielder claim
a Serie A winner's medal in the 1978–79 season.
But it was Capello’s managerial prowess that firmly established his name in the AC Milan
history books. About a decade after finishing his playing career and cutting his managerial
teeth with AC Milan Primavera, he took over as head coach in 1991.
Capello delivered a league title at the first time of asking. He went on to claim four of them in
five seasons: three Supercoppa crowns, a European Super Cup, and the biggest of all, the
UEFA Champions League title in 1993–94.
Carlo Ancelotti:
Ancelotti is one of the greatest managers in modern football. It's almost easy to forget that
he was a former AC Milan player. Ancelotti joined the Rossoneri from Roma in 1987 and
stayed through to the end of the 1991–92 season, making more than 100 appearances.
But much like Capello, Ancelotti’s playing days never put him in the limelight. That would
come from his club managerial career, which began with Reggiana in 1995. Ancelotti started
gaining recognition from his subsequent work at Parma before being taken on by Juventus.
From Juventus, he went to AC Milan for a long stint that saw him in the dugout for 420
matches. During his reign, the Rossoneri only won Serie A once in 2003-04, but it was
Ancelotti’s work on the European front that dominated, delivering three UEFA Champions
League titles.
Ancelotti would go on to become the first manager to win a title in all of Europe’s Big 5
leagues and is a five-time Champions League-winning manager.
Gennaro Gattuso
Such a fierce competitor on the pitch for Milan, Gennaro Gattuso took over as manager of
AC Milan in December 2017. The defensive midfielder was a beast in the famous black and
red and took his same gritty, determined, and committed style into his managerial career.
Gennaro spent two seasons in charge of AC Milan but failed to bring in any silverware during
that time. A costly miss in not reaching the UEFA Champions League in his first full season
in charge of the club saw the manager and club part ways in May 2019.
Filippo Inzaghi:
The much-loved forward spent more than a decade up front for AC Milan. The prolific
goalscorer won two league titles with AC Milan as a player and a couple of UEFA
Champions League crowns too.
A legend of the San Siro, Inzaghi was handed the managerial reins for the 2014-15 season.
It was a hugely unsuccessful partnership, however, for the former World Cup winner. Inzaghi
returned just a 35% win record for Milan as manager.
Cesare Maldini
Father of Paolo and club legend in his own right, Cesare Maldini, who won the European
Cup and four Scudetto honours with Milan, served as their head coach from 1972. After just
missing out on the title in 1973, Maldini was sacked the following year after poor results.
He returned in March 2001 as an interim head coach until the end of the season, which
included overseeing a record Milan Derby win of 6-0 over rivals Inter.
