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The Best Of Enemies: Manchester United And Real Madrid Transfer History (Part 2)

Cristiano Ronaldo’s transfer from Manchester United to Real Madrid was without a doubt one of the greatest and most drawn-out transfer sagas in football history, and it all began shortly after Manchester United rise to the top of the world as newly crowned 2008 European Champions.

Following Manchester United’s 2008 Champions League Final victory over Chelsea in Moscow, rumors circulated throughout the British press that Cristiano Ronaldo was set to leave Manchester United in favor of Real Madrid, a dream move for the player who had grown idolizing Los Blancos. However, Sir Alex Ferguson wouldn’t have it and convinced Cristiano to stay for one more year – a move vindicated by the fact that Ronaldo would go on to score 26 goals in all competitions that season. The next summer, like clockwork, Real Madrid came calling again, but the relations between the two clubs regarding the transfer were anything but cordial.

Throughout the 2008-2009 season, rumors of an agreement for Ronaldo between United and Madrid persisted in the Spanish media, prompting an incensed Sir Alex to say, “Do you think I would get into a contract with that mob. Jesus Christ, no chance. I wouldn’t sell them a virus.”

Despite the fiery claim, United’s manager had no choice but to relent and make good on the promise he made to his superstar player a year earlier. He would let Cristiano join his boyhood dream club, Real Madrid.

On June 26, 2009, Real Madrid confirmed the transfer and Cristiano Ronaldo achieved his dream of becoming a Blanco. The price for the transfer? A world record fee (until Gareth Bale’s Madrid move) of £80 million. The deal was sealed and Manchester United made a lot of money, but Manchester United and Real Madrid were anything but friends after the fact.

In terms of who won the transfer, Real Madrid no doubt acquired one of the best players on the planet, in his prime no less, and the deal is still paying off for them to this day. Meanwhile, United have struggled to replace Ronaldo, to say the least.

The next moves that took place between the two clubs occurred five years following the Ronaldo saga, in 2014, when Angel Di Maria and Chicharito swapped clubs during the summer transfer window. With Ferguson retired, relations between the clubs seemed to have thawed and Real Madrid agreed to sell Angel Di Maria to United for a whopping £59.7 million, the fifth highest transfer fee of all-time.

This particular move was a disaster for United with Di Maria never really settling in Manchester United colors – and now close to completing a move to PSG. Definitely a win for Real Madrid on that one.

That same summer Chicharito Hernandez joined Real Madrid on a one-year loan and, despite mostly coming off the bench, Chicharito still had a few moments of genius in him, in particular scoring the goal that would send Real Madrid into the Champions League semi-final last season.

Despite these heroics, Real Madrid did not take up the option to buy him and Chicharito was sent back to Manchester. Let’s call that move a draw.

So, what’s next for these two clubs and their dealings? Well, Madrid seem to have once again gotten under the skin of a Manchester United manager, this time Louis Van Gaal, with their persistent attempts to woo Manchester United’s starting goalkeeper, David De Gea. Simultaneously, Sergio Ramos seems to be using a rumored move in the opposite direction as a bargaining chip for a Real Madrid contract extension.

The De Gea move to Madrid seems inevitable with the latest reports indicating Manchester United has accepted defeat, but United refuses to do so quietly and they are demanding a record goalkeeper fee for De Gea.

Whatever the outcome, Real Madrid and Manchester United will probably do business again in the future, although the clubs are definitely not what you would call the best of friends. Perhaps a more fitting label would be Real Madrid and Manchester United: The Best of Enemies.  

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