It is always painful when a player is sold by your club that you are convinced could have had a lot more success, if they were just given a little more time. In the case of Real Madrid, almost every player they sell seems like a poor sale as they must have been really good to be at Real Madrid in the first place.
For a club that is so relentlessly at the top, there is rarely deadwood. Players tend to be moved on purely because the opportunity for an upgrade has arisen in the transfer market. Real Madrid are almost never selling players for a profit, the big money sales tend to be when the opportunity arises thanks to the buying club.
Occasionally though, even Real Madrid can make mistakes with their transfer business. Players they should have held onto for a lot longer than they did, and players who went on to enjoy extraordinary success elsewhere.
The following six all did that in some way, shape or form, with Real Madrid supporters perhaps left wondering 'what if'.
Mesut Ozil
Year of departure: 2013
Sold to: Arsenal
Mesut Ozil ended up having quite an unusual career. He was an extremely gifted footballer who had some great success, but there is still a feeling that he could have achieved even more. Things went downhill from both a club and international perspective at the end of his Arsenal stay, but he was superb at Real Madrid.
There were rumours that the arrival of Luka Modric in Madrid put Ozil's nose out of joint but he denied this and in his final season with the club, he recorded more assists than anyone else in La Liga. That was the third season in a row that he was the assist leader in La Liga. Despite that, Real Madrid opted to accept a £42.5m bid from Arsenal in September 2013.
He went on to snare 33 goals and 59 assists in 184 Premier League games and helped Arsenal to four FA Cups and one Community Shield. Based on those numbers and what he did in his final season at Real Madrid, surely there was still a use for him in Spain?
Angel Di Maria
Year of departure: 2014
Sold to: Manchester United
Somewhat similar to Mesut Ozil's situation, it was a surprise to many that Real Madrid were willing to cash in on such an incredibly talented footballer. It seems that Di Maria was largely a victim of Gareth Bale's arrival and the good start that the Welshman had, with Cristiano Ronaldo on the other wing. Perhaps if they'd waited one more year, Di Maria would have picked up the slack left by Bale.
Receiving a fee of £59.7m was deemed too good an offer for Real Madrid to turn down given Di Maria was not viewed as an automatic starter, and his spell at Manchester United may have left them feeling vindicated. He started very well, but an injury and some odd decisions from Louis van Gaal meant United saw nowhere near the best of Di Maria.
He joined PSG after one year and showed that he is still an elite footballer, playing 295 times, scoring 93 goals and getting an incredible 119 assists. Given the way that Bale's time at Real Madrid panned out, keeping Di Maria around, a player who wanted to stay, would not have been a bad choice.
Clarence Seedorf
Year of departure: 1999
Sold to: Inter
For football fans beneath the age of about 23, Clarence Seedorf is not a player that you remotely associate with Real Madrid. He arrived from Sampdoria in 1996 and was an instant hit. He won La Liga, the Champions League, the Intercontinental Cup and the Supercopa de Espana as a key part of the midfield.
Towards the end of his spell in Spain, his role started to be cut down by John Toshack, a coach he did not get on with. That led to him being sold to Inter, although they had tried to execute a swap with Juventus a year earlier that would have seen Zinedine Zidane arrive in Madrid.
It was a €24m move to Serie A and whilst he was liked by Inter's fans, he could not help them win any trophies. It was the move to AC Milan that showed Real Madrid what they had let go. He won Serie A twice, the Champions League twice, a Coppa Italia, a Supercoppa, the UEFA Super Cup twice and the Club World Cup.
Arjen Robben
Year of departure: 2009
Sold to: Bayern Munich
Arguably the best example, Arjen Robben was at Real Madrid in his prime but that is not where he played his best football. The winger arrived following a superb three-year spell at Chelsea, but he only managed two seasons at Real Madrid. He was a key player, scoring 13 goals and getting 15 assists across 65 games.
Florentino Perez's arrival as president of the club suddenly put Robben and others under pressure, as Cristiano Ronaldo and Kaka also arrived. Despite the fact that Robben was playing superbly and did not want to leave, he was shipped to Bayern Munich who spied the opportunity to sign a world-class winger for just €25m.
He won a mere 17 trophies at Bayern, including a Champions League in which he scored the winning goal against Borussia Dortmund. He got 144 goals and 101 assists across 309 games, and Real Madrid might feel they could have got more from his time at the club, or at least a bigger fee.
Esteban Cambiasso
Year of departure: 2004
Sold to: Inter (free transfer)
Another player who is not naturally associated with Real Madrid, Esteban Cambiasso really was let go too soon in the purest terms. The Argentine was actually an academy graduate, having arrived in 1996 from Argentinos Juniors.
He left the club for Independiente where he spent three seasons but then returned to Real Madrid, helping them win the UEFA Super Cup and the Intercontinental Cup in 2002, as well as La Liga and the Supercopa in 2003. After making 67 appearances, he was handed to Inter on a free transfer.
It is safe to say that he found a home in Milan, as he spent a decade with the Nerazzurri and won no less than 15 trophies, including five Scudetti and the Champions League in 2009/10 under Jose Mourinho.
Claude Makelele
Year of departure: 2003
Sold to: Chelsea
Not only did Real Madrid clearly let Claude Makelele leave the club too soon, there are quotes from Florentino Perez to make it even worse. Upon letting Makelele leave in 2003, Perez said: "We will not miss Makelele. His technique is average, he lacks the speed and skill to take the ball past opponents, and 90 per cent of his distribution either goes backwards or sideways."
He later added: "Younger players will arrive who will cause Makelele to be forgotten."
Makelele had asked for a new contract at Real Madrid given he was paid much less than similarly important players, and the club refused. That led to a transfer request and the bad blood. Steve McManaman described Makelele as the most important but underappreciated midfielder at Real Madrid in his autobiography.
Chelsea snapped the Frenchman up for £16.8m and he became a vital player. He helped Chelsea win the Premier League twice, the FA Cup once, the League Cup twice and the Community Shield. He was a key part of Chelsea's rise into being one of the Premier League's top sides.
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