You often hear the phrase ‘nice problem to have’ when discussing a manager’s dilemma of having too many talented players to choose from. The sheer number of quality, if not legendary, players who have worn the iconic Rossoneri shirt of Milan made this task nearly impossible. In the end, there were a few players who simply could not be left out, no matter the circumstances. The 'nice problem' of having so many options wasn’t so pleasant when I had to leave out some of my favorite players. Nonetheless, the five I selected would be unbeatable.

There was a famous Nike billboard advert during the 1998 World Cup featuring Paolo Maldini. It showcased the defender’s image with the line ‘Italy’s goalkeeper: Easiest job in Europe’. The keeper I chose for my five-a-side team benefited from playing behind Maldini throughout his tenure as Milan’s No 1.

Sebastiano Rossi joined Milan in 1990 at the age of 26 as a backup to Andrea Pazzagli. Within a year, Rossi had claimed the No 1 shirt and his position behind one of the greatest defensive lines in football. This does not mean his job was as easy as the Nike advert suggested. The quality of the defenders in front of him might have led to Rossi being somewhat underrated.

Rossi held the record for consecutive minutes without conceding a goal in Serie A until Gianluigi Buffon broke it over a decade later. Twelve years with the Rossoneri saw the keeper lift the European Cup as well as five Scudetti, three Italian Super Cups, and two European Super Cups. Despite being close to selection, he never represented his country. There cannot be many keepers as good as Rossi who did not receive even a single cap.

In my opinion, there isn’t a modern-day player comparable to Franco Baresi in terms of his playing style. He was never the tallest, fastest, or strongest of central defenders, but he was always one of the best. Baresi was more cerebral than his contemporaries, always knowing where to be and what to do on the pitch.

Baresi debuted for Milan at the age of 17 and went on to lift the Serie A title a year later as a regular in the side at just 18. This marked the beginning of a 20-year playing career, including 15 years as captain. A one-club man who led Milan through a glorious period in their history, he lifted the European Cup three times and the Italian title six times. Add in four Italian Super Cups, three European Super Cups, and two Intercontinental Cups, and it’s clear why Baresi is a legendary figure.

A five-a-side team probably doesn’t require two defenders. However, I had to pick two. If Baresi isn’t the greatest Milan defender of all time, then Maldini is. Another one-club man, Maldini came through the youth system at the club where his father was already a famous figure. He joined Milan at the age of 10 and made his debut in the first team at 16. It was the first of 902 official matches for the Rossoneri over the next quarter of a century, inheriting Baresi’s captain’s armband along the way.

Maldini emulated his father’s achievement of winning the European Cup, going on to lift the famous trophy five times over his career. He also picked up seven Scudetti. In my view, Maldini is the greatest defender of all time. He had everything you would want in a defender. A naturally right-footed player who made his name as the world’s greatest left-back, Maldini was also one of the best central defenders on the planet.

I only had one midfield place left in my team after the inclusion of both Baresi and Maldini. The fact that so many amazing midfielders are missing out probably makes this the most contentious of my choices. Rivera’s record speaks for itself, and the fact that I know about a player whose Milan career ended the year before I was born shows his importance still resonates.

A player who was ahead of his time in terms of ability and vision, Rivera was known as ‘Golden Boy’ by the Italian media. The moniker came with good reason as he was awarded the Ballon d’Or in 1969, the award coming a year after he led Italy to winning the European Championship. He may have played in a time when Italy was famed for their defensive solidity, but Rivera was the classy playmaking yin to the Azzurri’s defensive yang. Three Serie A titles and two European Cups were lifted by Rivera, who like Baresi and Maldini, wore the captain’s armband. He made over 500 Milan appearances in a near 20-year spell, more than earning his place here.

I almost picked an all-Italian lineup but could not resist picking this Dutchman as my striker. He is one of the greatest forwards to have played the game, and had injury not curtailed his career, he may well be thought of as the greatest. Van Basten arrived at Milan in 1987 as the Rossoneri won their first Serie A in eight years. The Dutch goalscorer was ruled out for most of his debut season with injury but made up for it the following year, leading the Netherlands to the European Championship title while picking up the Ballon d’Or and scoring possibly the greatest goal of all time.

He was not just a goalscorer; there was more to his style than that. Van Basten oozed class in everything he did, and the ball appeared stuck to his feet at times as defenders tried in vain to dispossess him. He was as adept in the air as he was on the ground and not just in terms of headers. He was not averse to a spectacular overhead kick. A three-time Ballon d’Or winner while at Milan speaks to his talent, as does his four Scudetti, three European Cups, and 125 goals in 201 games.

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