The goal that ultimately won the 2007 UEFA Champions League final for AC Milan could not have been a better representation of both the quality and style of play of one of Milan's greatest generations.
They led Liverpool 1-0 late in the second half of that match, and the Reds were piling on the pressure. Liverpool were the more ambitious-looking side throughout the match, and they were forcing Milan onto their heels as they pushed for an equalizer. In the 82nd minute, Liverpool's back line got caught napping and were undone by a Kaka through ball to Filippo Inzaghi, who ran onto the ball, rounded Pepe Reina and finished calmly.
Inzaghi might have been a hair offside, but then again, when hasn't be been during his career? Might Have Been A Hair Offside should probably be the title of Pippo Inzaghi's autobiography. His generation has contained quite a few better all-around forwards, but not even a handful of better pure goal-scorers. No one is better at sitting on the back shoulder of the last defender and picking the right moment to pounce.
Dirk Kuyt scored in the 89th minute to make things interesting, but Liverpool couldn't find an equalizer and Milan ran out 2-1 winners, capturing a bit of revenge against Liverpool for their defeat at the hands of the Reds in Istanbul two years prior. The Champions League win came less than a calendar year after six of the players on Milan's roster had won a World Cup with Italy. It was the last of five Champions League titles for veteran defenders Paolo Maldini and Billy Costacurta.
This was arguably Milan's greatest ever generation at their best. Some of their aging stars would milk their Milan careers for another five years afterwards, but this was the beginning of the end. New signings mixed in well with the Rossoneri's old guard over the last two seasons to guide them to one last Scudetto and a runners-up performance, but Milan is finally done clinging to their golden generation, and the golden generation is moving on from them as well.
Milan's legends have served them well, but it's time for a change at the San Siro.
Maldini made his first team debut for Milan in 1985. Costacurta's debut came one year later, in 1986. They played for a brilliant group of Milan teams in the late 1980s and early 1990s. At that time, they were the young stars that extended the career of the legendary Franco Baresi, one of the greatest defenders of all time and possibly the best player to ever play for AC Milan. Little did anyone know that in the 2000s, the likes of Baresi, Roberto Donadoni, Mauro Tassotti and Marco van Basten would be doing the same for them.
The assembly of a team that would play together for a decade began shortly after Milan won the 1998-99 Scudetto. Youngster Gennaro Gattuso began playing regularly. Andriy Shevchenko arrived and made an instant impact, scoring 24 goals in the league in his first season with the club, displacing Oliver Bierhoff and George Weah as Milan's top striking option. Left-sided star Serginho arrived in 1999 as well. Massimo Ambrosini, who played regularly in the 98-99 season, began to see even more time.
Dida arrived the following season, but would not become the starting keeper until 2002. Kakha Kaldazhe, who along with Dida played for Milan for a decade, arrived during the winter. Milan finished 6th in Serie A and were knocked out of the Champions League by Deportivo La Coruña. Silvio Berlusconi was elected Prime Minister of Italy, while Alberto Zaccheroni was fired. It was very much a down year for Milan, but the following season's transfers and appointments were among the most important in Milan's history.
The list of players that joined Milan over the next two summers is staggering. Inzaghi, Manuel Rui Costa, Andrea Pirlo, Clarence Seedorf and Alessando Nesta all joined the club in 2001 and 2002. Promising youngster Kaka joined in 2003 along with Cafu, who was universally regarded as the best right back in the world.
All of Gattuso, Ambrosini, Kaldazhe, Dida, Inzaghi, Pirlo, Seedorf and Nesta would go on to play at least 10 seasons with A.C. Milan. Serginho played nine. Shevchenko played seven. Rui Costa, Kaka and Cafu all played five. There was a stretch of three seasons where all 13 of these players plus Costacurta and Maldini were on the same team.
Rui Costa and Shevchenko left in 2006, leaving 13 of those players on the squad for the 2007 Champions League final. All 15 players were on the team for Milan's 2003-04 Scudetto win, their 2002-03 Champions League title, and the heartbreaking loss in Istanbul in the 2005 Champions League final. They were also runners-up in Serie A in 2004-05. Six of these players -- Gattuso, Inzaghi, Seedorf, Nesta, Pirlo and Ambrosini -- were on the team that won last season's Scudetto.
Considering how incredibly stacked this team was and the incredible level of cohesion the players had with each other, it's astonishing that they didn't win more trophies. Two Scudettos and two Champions League titles is nothing to scoff at, but the Italian internationals on this team won World Cups. Costacurta and Maldini were too old to go to the 2006 World Cup, but made the semifinals on two previous occasions with Italy. Kaka and Cafu won the 2002 World Cup with Brazil. Shevchenko scored 175 goals for Milan before Chelsea paid £31 million for him.
Their lack of trophies -- relative to the talent and longevity of the team -- is a real testament to the strength of Italian football in the first half of the 2000s and the strength of English football in the second half of the decade. As Maldini and Costacurta were beginning to fade, players like Francesco Totti, Javier Zanetti, Gigi Buffon, Alessandro Del Piero and Pavel Nedved were in their primes. The Premier League became a giant on the back of television contracts and foreign investment. Milan competed with English teams that had more financial backing and Italian teams that had bigger attacking star power, but never quite accomplished everything they should have, at least domestically.
As good as Juventus, Roma and AC Milan were in the last decade, it feels like Milan won more than they did. They had the more memorable teams, the more memorable set of players, and they were the most consistent team over the course of the entire decade. The two-year stretch of 2003 and 2004 was their high point. They won the 2002-03 Champions League and Coppa Italia, then the 2003-04 Scudetto in the season where they stunningly and inexplicably collapsed in the Champions League quarterfinals against Deportivo La Coruña, their European bogey team.
For that stretch -- before Juventus hit their pre-Calciopoli peak, before Roman Abramovich bought Chelsea, before Ronaldinho was the best player in the world and before Manchester United had Wayne Rooney and Cristiano Ronaldo at their best -- Milan really were the best team in the world. They're more notable for their consistency than they are for any point of true brilliance, but they had a short run as the world's best.
The only mistake that Berlusconi and his staff made during the latter part of the decade was not recognizing what was going on around them. Milan's stars were aging while Inter Milan, Barcelona, Liverpool, Manchester United and Chelsea were getting better. Through some combination of bad luck and incompetence, Milan didn't make as much money as they should have during their biggest period of success. They couldn't buy top reinforcements and they had to sell Kaka in 2008. Alexandre Pato never became the next great Rossoneri star. Slowly but surely, Milan became less relevant from the 2006-07 season until 2010, when their fortunes were reversed, culminating in their surprise 2010-11 Scudetto win.
Milan's golden generation has been on life support since the 2007 Champions League final, and they've been propped up in recent years by Zlatan Ibrahimovic, Kevin Prince-Boateng and Thiago Silva. Milan rode their old guard into this decade, but the golden generation has finally fallen apart. Pirlo's departure to Juventus last summer was just the beginning. All of Inzaghi, Nesta, Seedorf and Gattuso will be leaving Milan over the summer, nearly dissolving the golden generation for good. Only Ambrosini remains.
While a number of young stars and players in their prime remain at Milan, they are now a team in need of some rebuilding. Their best ever team is finally gone for good. Riccardo Montolivo has already been signed, but he won't fill Pirlo's hole by himself, much less those left by Nesta, Seedorf, Inzaghi and Gattuso. Milan's old guard was stellar, but the curtain has come down on their careers with the Rossoneri, as the lingering members of the early 2000s teams choose to exit.
Even as they leave, Nesta, Seedorf, Inzaghi and Gattuso continue to serve Milan. With their departure, the four legends have done one last favor to Silvio Berlusconi. They've taken away his option to continue to cling to the past.