“What does this player have in his boots? A magnet?” Sir Alex Ferguson was bewildered. It’s April 19, 2000 and his Manchester United side, then reigning champions of Europe, had just been dumped out of the Champions League by Real Madrid at Old Trafford in a pulsating tie.

Yet there was one moment in the game that everyone from the managers to the players to the fans in the stadium to those watching at home were talking about, a moment of genius that would transcend time, and poor Henning Berg just never saw it coming.

In the 52nd minute of the game Fernando Redondo went on a slalom run down the left hand side of the Old Trafford turf, with Berg in pursuit. There was seemingly nowhere for the Argentine to go as he ran towards the touchline, then in a piece of individual brilliance that is amongst the finest in the history of the competition, Redondo majestically back heeled the ball diagonally through the Norwegian’s legs, darting around the defender and regaining the ball inches before it was about to go out of play. He made inroads to the United goal before squaring the ball to the onrushing Raúl who tapped in to make it 3-0 to Real Madrid. You could hear a pin drop inside the Theatre of Dreams.

Despite a valiant fight back from the home side inspired by David Beckham, Redondo’s act of sorcery was the coup de grace on a fine Madrid performance. Years later Iván Helguera admitted that they felt some trepidation going into the game: “The truth is, we were pretty scared.” Real were struggling in the league while their opponents were running away with the Premier League title and had thrashed West Ham 7-1 the weekend prior to the first leg.

Before the first game in Madrid, Amy Lawrence of The Guardian wrote a piece where she described Redondo: “[A] volatile, unyielding Argentine midfielder who, with Hierro, is a big influence inside the Bernabéu. He’s great with his elbows: should be an interesting duel with Keane.” Anyone who had seen the midfielder’s sumptuous talents for Real or Argentina knew this was doing him a gross injustice.

By the end of the second leg in Manchester, Redondo had proved to a UK audience that he also had great feet to go along with his great ‘elbows’. While Raúl got the majority of the plaudits for his two goals, many recognised that Real’s no.6 was the architect of the victory.

Redondo comprehensively outmanoeuvred United’s midfield in a manner which nobody could at the time.

He had succeeded where a year earlier Edgar Davids and Zinedine Zidane had failed; the most feared midfield quartet in Europe were not only contained but given a master class in ball retention and midfield orchestration by the Argentine. Roy Keane had never been so thoroughly dominated in a single game, especially not this Roy Keane, at the physical peak of his career. His gorgeous back-heel encapsulated his overall performance.

Raimond van der Gouw, United’s goalkeeper that night claimed “that back-heel killed Henning Berg”. A few months later Berg would leave the club. “If he had done it to me, I’d have kept running to Buenos Aires,” said Iván Campo jokingly, who played in central defence that season for the Spaniards. “That was the play of the year, it didn’t surprise me that Fernando tried it but it did surprise me that it came off so, so cleanly,” he added.

Watching the back-heel time and again, there is an elegance to the entire sequence that you rarely see in the modern game, akin to watching Michael Jackson execute the moonwalk. Redondo seemingly glides over the pitch, consciously in control of the situation. He retrieves the ball in his own time and with a zen-like calm bides his time to pick out a Real player and precisely strokes the ball across the box for Raúl to slot home. Amongst a contingent of Los Blancos fans it became immortalised as the ‘Backheel of Old Trafford’.

Next up was Bayern Munich in the semi finals. The German’s had demolished them by an aggregate 8-3 score line in the second group stage and most favoured Die Roten to advance to their second consecutive final.

Now, with a renewed sense of confidence after the win at Old Trafford, Madrid, led by Redondo, shone brightly as the Argentine was once again instrumental with the Spaniards winning 3-2 on aggregate and against all odds found themselves in their second final in three years.

The first ever same-country Champions League final in Paris on May 24 was a one-sided affair as Redondo and his team steamrolled over Valencia in emphatic fashion. Once more he was marvellous in instigating Madrid’s play, passing and probing his way around the pitch with his usual languid elegance.

Now at the pinnacle of his game with his second Champions League winners’ medal and having received the recognition that his abilities richly deserved, the 30-year-old was on top of the world. He would later win UEFA Club Footballer of the Year for his exploits. As Redondo was presented with the big-eared trophy and held it aloft into the Paris night sky, little did he or anyone know that it would be his last competitive game for a long time.

The summer of 2000 was a seismic season of change at Real Madrid. Lorenzo Sanz, the president of the club since 1995, was standing for re-election and was up against a then largely unknown Florentino Pérez. Sanz banked his credibility on the fact that under his presidency the club had won two Champions League titles in three years, with the first one in 1998 ending their 32-year wait.

Pérez, by contrast, pointed out the mind-boggling debts that had been racked up after years of mismanagement from his rival candidate and catered to voters with the promise of signing Luís Figo from eternal rivals Barcelona if elected.

Six weeks after winning their eighth European Cup, the election began. Redondo sided with Sanz, and Sanz lost. Pérez achieved the victory by more than 3,000 votes. A week later, true to his word, Luís Figo duly arrived at the Santiago Bernabéu for a world record €62 million. The era of the Galácticos had begun.

Following further purchases of Claude Makélélé and Flávio Conceição, Pérez now needed to sell players in order to improve the crippling debts that he promised to eradicate during the election process. The problematic Nicolas Anelka was sold to PSG and Christian Karembeu was offloaded to Middlesbrough. Finally, foreshadowing events that would happen to Makélélé himself three years later, the president turned his attention to the midfield engine of the side: Redondo.

Knowing that he had backed his presidential rival during the election and with the influence the Argentine wielded in the dressing room, and given how he had just turned 31, Pérez controversially began to engineer the sale of Redondo – without the player’s consent.

In northern Italy, Silvio Berlusconi and Adriano Galliani were growing restless. Even by the ‘lure of the lira’ standards of Serie A in the 1980s and 1990s, the summer of 2000 saw Italian sides take excess to another level. The pair had watched Juventus sign David Trezeguet, Lazio, the newly crowned Serie A champions, sign not only Valencia striker Claudio López but also break the world transfer record by signing Hernán Crespo, and Roma finally persuade Gabriel Batistuta to leave his kingdom in Florence for the Eternal City. Milan had done little business and such is the Berlusconi way, they needed a big star of their own in this game of footballing one-upmanship.

As word seeped through the football landscape that Pérez wanted to cleanse his new club of players who identified with the Sanz era, Galliani and Ariedo Braida were packed on a plane heading to Spain.

Inter were the first Italian team to express interest, but this was rejected both by Redondo and Vicente del Bosque – manager at the time – who objected to any notion of the player leaving. As it was made clear to the Madrid coach that his star would be sold, his stance softened to a degree.

Galliani and Braida met with Pérez at a lavish hotel in Mallorca to open talks over the Argentine. After some initial haggling over the price of the player, the good relations between both clubs ensured that a deal would happen. A deal of £11.25 million was agreed.

Now the real difficulty was trying to sell the move to Redondo, who felt like a true Madridsta and was cherished not only by everyone at the club but also by the fans. On July 26 he gave an interview in which he said: “I feel totally integrated at this club. For me, there is no reason to go and play for another club.” Adding that, ‘’I repeat, Real is my home, and as far as it depends on me, I see no reason to desire another”.

Shrewdly aware that Pérez wanted to sell him and that in the eventuality he might have to leave the Spanish capital, he made sure to make it public knowledge that he was being forced out by the new president: “If Real do not want me anymore, it is clear that one way is to get rid of me.”

Two days later after much deliberating, Redondo reluctantly agreed to sign for Milan. Everyone was happy – Berlusconi got his star name, Galliani and Braida pulled off a great deal and Pérez had got rid of an influential Sanz supporter. Everyone, that was, except for the player at the centre of it all. True to his outspoken nature, he wouldn’t leave quietly. The mud slinging began.

On their website Real posted: “Real Madrid would like to officially announce the agreement reached today between Fernando Redondo and AC Milan.”

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Read  |  The pioneering AC Milan Lab that extended players’ careers

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Correctly sensing that their fans would be furious with the sale of their captain and midfield fulcrum, they intelligently inserted “this transfer has come about as a result of the expressed desire of the player”.

Redondo, who was incensed at their attempts to shift the responsibility on to his shoulders, released a statement shortly after counter-acting Madrid’s version of events.

“I want to give you the facts. Nobody from Real Madrid contacted me to tell me what was happening until Wednesday night. Then I was told that Milan’s offer was very interesting for the club and a fee had been agreed. I was told that this information had already been passed to my agent. I phoned him and he confirmed that he had spoken to Milan and that the deal was agreed.”

He added: “I understood the situation but it was not my decision to leave. The club wanted me to go and I was in an impossible situation, I refuse to allow this stain on my name and image.”

Del Bosque tried to hide his displeasure at the departure of his midfield general, saying: “Nobody is irreplaceable, but I will always love Fernando. The player is smiling, he seems very content and he is working very well. He is a great professional.”

As expected the Madrid fans were furious as the news filtered through. A crowd of fans gathered outside the Bernabéu to vent their anger, chanting ‘we won’t swap Figo for Redondo’ and ‘Redondo is Madrid’. Galliani’s car upon recognition was kicked at by Madrid ultras, blaming him for the departure of their beloved idol.

Coincidentally, both sides were shortly due to play each other in a friendly to celebrate Milan’s centenary, and such was the controversy over the Redondo transfer both sides had discussed cancelling the match. Ultimately it went ahead – with Redondo sitting beside Berlusconi in the stands.

“When we put the results of Redondo then into our system now, he comes out as a tremendously high risk,” reflected Jean-Pierre Messerman – creator of the famed Milan Lab – in an interview several years ago.

The common perception is that a day after signing for Milan Redondo’s career ended whilst running on a treadmill for a few minutes; that his right knee broke down after passing a thoroughly rigorous medical. That’s only partially accurate.

On his second day as a Milan player he hurt his right thigh whilst on the treadmill, however it wasn’t just the incident on the treadmill that effectively ended his career. Two weeks later in the plush environs of Milanello, whilst training, he planted his right foot into a hole on the ground that due to rain was soft, suffering a first-degree sprain of his knee. Incredibly, he completed the training session before seeking help. This was the deathblow, and neither his knee nor career would ever fully recover.

As the weeks passed, with his knee imploded and showing little sign of recovery, it was recommended that he undergo surgery, and so on October 2 the Argentine’s anterior cruciate ligament was reconstructed in Varese by professor Paolo Cherubino, who disclosed in a press conference that he expected Redondo to return to the field in six months.

Berlusconi was irate: how could this have happened? Rumours swirled around Spain that Real Madrid knew he was broken and had sold Milan a crock, yet Professor Cherubino reported that Redondo was simply unfortunate and excluded chronic illness in his knee, also adding that the tests completed in his medical showed his right knee was in perfect condition. Milan’s owner, however, wasn’t buying it, and vowed never to let it happen again, hence the creation of the Milan Lab two years later.

Redondo would need a further two surgeries to finally repair his knee. He flew back to Madrid in June 2001 for the second operation following complaints of severe pain in his knee during rehabilitation; his patellar tendon had become inflamed upon examination.

In an act of integrity and moral dignity that is rarely seen in the gluttonous world of football, in August 2001 Redondo went to see Galliani and told him that the club should stop paying his wages until he regains fitness. “I have never seen anything like it during my career as a director. Fernando is an incredible man,” Galliani remarked. Not content with just giving up his salary, he also wanted to give back his car and house that Milan gave him as part of his contract but the club rejected his proposal.

His final operation took place in January 2002 and Redondo made his long awaited debut for the Rossoneri on the December 3 against Ancona in the Coppa Italia – some 29 months after signing.

He made his Serie A debut several days later against Roma, receiving a standing ovation from the 67,000 fans inside the San Siro as he came on for Andriy Shevchenko for the final five minutes. for the Rossoneri on the December 3 against Ancona in the Coppa Italia – some 29 months after signing.

In classic Redondo fashion he made a mockery of Walter Samuel and Emerson in the same move, taking them out of an equation with a beautiful Cruyff turn.

Redondo’s past would meet his present once more as Milan and Real were both drawn in the same second group stage in the Champions League.

On March 12, 2003, Milan travelled to the Bernabéu having already qualified for the quarter-finals. Sensing an opportunity to give Redondo the send-off he was denied by Pérez, Carlo Ancelotti started Redondo instead of regular Andrea Pirlo. “I’m very happy about seeing my former supporters again and this is a very special moment for me,” he said before the game.

As Milan and Redondo walked out to begin the match, the crowd stood up and chanted his name for several minutes and in the 79th minute Pirlo replaced him to a rapturous applause from the home supporters. The Madrid fans unfurled a banner saying ‘God returns to paradise’. It was the goodbye his contributions undoubtedly warranted.

It was clear to everyone that unsurprisingly he was no longer the Redondo of old, but was offered a one-year extension by Milan as a gesture of good faith. He was used sparingly for the remainder of 2002-03 and the 2003-04 seasons yet still won a Coppa Italia, another Champions League and a Serie A title during his stay. His last competitive game was on May 16, 2004, against Brescia and, after leaving Milan, he announced his retirement.

Fernando Redondo was one of the finest midfielders of the last two decades, blessed with a fine mix of delicate balance, predatory vision and strong leadership capabilities, he was a football purists’ utopian dream, an artist in an era where their numbers dwindled as the game increasingly relied more on power and pace as oppose to ingenuity and technique.

Yet his injuries meant he receded from public view and has almost fallen into obscurity. He certainly would have been in the running to win the Ballon d’Or in 2000 yet didn’t make the top ten. It’s arguable that his injuries also changed the fate of Andrea Pirlo’s career; if Redondo was healthy and playing would Ancelotti have deployed Pirlo as a regista at Milan?

Regardless of the fate that befell him in Italy, El Principe’s career and talent deserves to be celebrated for the brilliance that it was. Recently voted in Real Madrid’s greatest foreign XI, he endeared himself to fans across Europe with his style. Real Madrid and Argentina have been waiting for a truly graceful volante ever since.

By Emmet Gates. Follow @E_I_M_G