As far as entrances go, it doesn’t get much more epic than arriving in a helicopter to the tune of Wagner’s "Ride of the Valkyries." That is exactly how Silvio Berlusconi chose to usher in a new AC Milan era on July 8, 1986.
The early 1980s had been extremely turbulent for the Rossoneri. The club had twice been relegated to Serie B; firstly because of their involvement in the Totonero match-fixing scandal, secondly because they simply weren’t good enough to stay up.
Berlusconi took over Milan on February 20, 1986, with the intention of returning them to the pinnacle of European football. Over the ensuing decades he would fulfil this ambition, often spectacularly, though his reign is now set to come to an end.
After over 30 years as owner, the 79-year-old agreed to sell the club to a Chinese consortium in early August, with Sky (h/t Football Italia) reporting that the deal will be completed by November 4.
With Berlusconi’s ownership nearing its conclusion, Bleacher Report takes a reminiscent look at the highs and lows of his time in charge.
In Berlusconi’s first full season as Rossoneri owner, the club finished fifth in Serie A and were knocked out, rather disappointingly, by second-tier outfit Parma in the Coppa Italia’s round of 16.
Months later, the man who had inspired the Crociati’s surprise victory was appointed Milan head coach.
Arrigo Sacchi had never been a professional footballer, and his time in coaching comprised of spells with Rimini and Parma in Serie C1 and B.
He was a relative unknown to many in the Italian game and was criticised for a lack of top-level experience. Averse to taking a backward step, he fired back at his critics: “I never realised that to be a jockey you had to be a horse first,” per FIFA.com.
His impact was instant; his debut year at the San Siro culminated in Milan winning their first Scudetto for nine years, losing just twice in 30 league games. He also introduced progressive tactical concepts such as a high defensive line, zonal marking and pressing.
Berlusconi has often been criticised for his decision-making in hiring coaches and signing players, but his appointment of Sacchi was visionary and highly influential in changing the course of Rossoneri history.
Winning, and retaining, the European Cup
Following their domestic success, Milan set out to conquer European football in 1988-89. Frank Rijkaard was added to the squad, joining fellow Dutch internationals Ruud Gullit and Marco van Basten; all three would play pivotal roles for the club.
With a fearsome all-Italian back four of Mauro Tassotti, Alessandro Costacurta, Franco Baresi and Paolo Maldini, Sacchi’s side were built on solid foundations, though it was their foreign stars who attracted the most attention.
Rijkaard, who had made his name as a centre-back, was deployed in central midfield alongside Carlo Ancelotti to good effect, while Gullit and Van Basten, each of whom had struggled during their maiden campaigns with Milan, formed a tantalising attacking partnership of strength, guile and technical mastery.
The Rossoneri hadn’t won Europe’s most coveted club trophy for 20 years, but that would soon be rectified.
After a 1-1 draw in Madrid, a 5-0 win at the San Siro courtesy of a goal apiece from the Dutch trio, as well a stunning long-range strike from Ancelotti and an accurate finish from Roberto Donadoni, ensured that the Rossoneri were one win away from being crowned kings of their continent.
In the final they met the Steaua Bucharest of Gheorghe Hagi, Dan Petrescu and Marius Lacatus, but the match was no contest. Milan were 3-0 up by half-time courtesy of a Gullit double and a Van Basten header, and another goal for the latter just after the break sealed a 4-0 win.
The following season, Sacchi once again took his side to the final, defeating HJK Helsinki, Real Madrid, Mechelen and Bayern Munich before a 1-0 win over Benfica saw the Rossoneri lift their second successive European Cup. No other team has retained the title since.
Invincibles and failures
Despite their extraordinary achievements abroad, Milan went three years without a Scudetto between 1988 and 1991. As a response, Berlusconi decided to bring in new talent, including agile goalkeeper Sebastiano Rossi, creative midfielder Zvonimir Boban and intelligent attacking duo Daniele Massaro and Marco Simone.
Furthermore, Sacchi, who went on to manage the Italy national team, was replaced by Fabio Capello as head coach.
While initial reaction to his appointment was predominantly sceptical in nature, the new man in charge retained the tactics of his predecessor while integrating new players to return Milan to dominance both in Italy and Europe.
Capello led the team to a Scudetto in 1991-92 without losing a single game along the way, and the unbeaten run continued into the next term. Berlusconi continued to invest, bringing in the likes of Dejan Savicevic, Jean-Pierre Papin and Gianluigi Lentini, whose signature for £13 million broke the transfer-fee world record at the time.
In total, Milan went without defeat for a remarkable 58 matches, earning the nickname "Gli Invincibili," or "The Invincibles." There was simply no competition in Serie A.
Having marched to three consecutive Scudetti, Capello then oversaw what was arguably the finest team performance in the history of European club football, as his Rossoneri took apart Johan Cruyff’s Barcelona in the 1994 Champions League final, winning by four goals to nil.
These were heady times, but before too long, Berlusconi, whose business beginnings were in construction, had a huge rebuilding job on his hands.
Following another league title in 1996, Capello was lured away by Real Madrid. At the same time, much of his iconic Milan side were ageing or had already departed. Their replacements simply didn’t live up to the club’s ambitions.
Oscar Tabarez lasted less than half a season as manager, with Sacchi returning to replace the Uruguayan in the dugout in December 1996. A deeply disappointing 11th-place finish followed.
Capello was then reinstalled as head coach but could only lead the team to 10th in Serie A. And, with signings such as Ibrahim Ba, Patrick Kluivert and Christian Ziege all failing to inspire a turnaround, the two years between 1996 and 1998 were Milan’s worst since Berlusconi had bought the club.
Throughout his time in football, there have been allegations of Berlusconi being an Interista. As John Foot wrote in Calcio:
For years, an urban myth to this effect was doing the rounds but the truth wasn’t confirmed until 2004 by the sports daily Tuttosport. Berlusconi always denied the story, saying that "I have never been an Inter fan, you can’t change your religion." But in 1980 he had even tried to buy Inter and, as many journalists have pointed out, only an Inter fan could possibly want to buy Inter.
The rumours may have persisted, but Berlusconi’s Milan have frequently had the better of proceedings against their city rivals.
Gianni Comandini is unknown to most, but his name will forever be remembered by Milanisti. The striker scored just two goals in Serie A during his time with the club. However, both of them came in a defining derby win on May 11, 2001.
His first was classic poaching, lingering in the penalty box before coolly slotting home; his second was a bullet header. Within 20 minutes, he had given Milan a 2-0 lead, a score that would be trebled come the final whistle.
The 6-0 result was both Inter’s worst home defeat in league action and the Diavolo’s record win in the Derby della Madonnina.
Two years later, the clubs met in the semi-finals of the Champions League and, once again, Milan would come out on top, triumphing on away goals after a 1-1 aggregate draw before lifting the trophy with a penalty shootout success over Juventus.
Istanbul and revenge
Few nights have been more painful for Rossonero than May 25, 2005. That evening in Istanbul, they watched on as their team squandered a 3-0 lead in the Champions League final to draw 3-3 with Liverpool before losing on penalties.
“I thought about quitting because, after Istanbul, nothing made sense any more,” Andrea Pirlo wrote in his autobiography, I Think Before I Play. “The 2005 Champions League final simply suffocated me.”
Two years later, Milan got their revenge, beating Liverpool 2-1 in Athens to lift their second Champions League title under Carlo Ancelotti’s auspices.
The 2007 victory owed a lot to the Milan Lab, a facility set up five years previously that helped to prolong the careers of several Diavolo players, including Maldini, Clarence Seedorf and Filippo Inzaghi. Indeed, the Rossoneri’s lineup that night was the oldest in Champions League final history.
For all the great moments throughout his time atop the club hierarchy, Berlusconi’s ownership of Milan has been under serious scrutiny in recent years. His managerial hiring and firing hasn’t helped matters.
He attacked Ancelotti in the press following a third-place finish in 2009, telling La Repubblica (h/t the Guardian’s Dominic Fifield): “We lost the title because of Ancelotti. Many times we did not use the right tactics. We have so many good dribblers and should have based our football on this asset but we did the opposite.”
Within months, Berlusconi was searching for a replacement coach.
Massimiliano Allegri succeeded Ancelotti and led the club to another league title in 2011 but was sacked after a disappointing start to the 2013-14 season. Up until the recent appointment of Vincenzo Montella, he was never properly replaced, with inexperienced former players including Seedorf, Inzaghi and Cristian Brocchi all unable to turn Milan’s fortunes around.
The last three years have been particularly taxing, with eighth, 10th and seventh-place Serie A positions ensuring the worst period in Berlusconi’s time as owner.
However, in spite of his poor decision-making and the subsequently underwhelming results evident in recent seasons, it would be wrong to ignore the part his investment and ambition played in the successes of the past.
When Berlusconi does officially move on, an important chapter in Milan’s history will come to a close. The end may not be as spectacular as the beginning, but much of the in-between lived up to the grand helicopter entrance.