Happens all the time.
Sometimes its understandable, often baffling.
Here are some that remain, well, regrettable:
Juan Roman Riquelme - Barcelona
You look at Barcelona, look at the way they play football, the ceaseless economy and beauty of that passing carousel, and its difficult to imagine any player could improve such a team. But Riquelme, the most talented Argentine footballer between Maradona and Messi, is perhaps the best passer of the ball of his generation from anywhere in the world, an unerring magician with vision and wonderful technique and an understanding of tempo and space even Xavi, for all his undoubted gifts, cannot replicate. Riquelme also scores goals and takes set pieces. He was signed in a blaze of publicity, another "new Maradona", the heartbeat of an all-conquering Boca Juniors side who had beaten Real Madrid to be crowned Club World Cup Champions inspired by an impeccable Riquelme performance which had made Zinedine Zidane look positively ordinary. But it never worked out for him. Bought in 2002 for €11 million, his transfer was overshadowed by the kidnapping of his brother just before he left Boca, where his departure had been controversial due to his refusal to sign a new contract over a long few months. Coach Louis Van Gaal didn't want him, wasn't shy about saying so (he famously called him a"a political signing"), and kept his new Number 10 mainly on the bench, playing him on the wing when he played him at all, and then in Cup matches and dead rubber European ties. That didn't work and Barcelona struggled. Another post-Van Gaal season with multiple coaches, a squad made up of many talents but no real identity, and big failures in the League and Europe made Riquelme something of a scapegoat among Barca fans, who had expected him to turn around their club. He was loaned to Villarreal when Ronaldinho was signed. The Brazilian, alongside Messi, would spark the Barcelona revival that continues to this day. As Riquelme could have, given the chance. As it was, he was instrumental in guiding Villarreal to unprecedented League success and a Champions League Semi-Final, and won Boca Juniors the Copa Libertadores upon his return to his beloved hometown club. But I can still see him, picking out Messi runs with those casually perfect passes. In reality, he scored 3 goals in 30 games for Barcelona, mainly as a substitute. He wouldn't quite fit with the ethos of the modern Barca - his talent is restricted to a single role and is best expressed when he is the fulcrum of a teams entire attacking dimension, but he had the talent to succeed when he did play there. Its just a shame that he was never really given the chance.
Diego Forlan - Manchester United
If, in August 2004, when Man Utd sold Forlan to Villarreal, you had told a Man Utd fan that he would twice win the European Golden Boot over the next five seasons, they would have laughed at you. The Uruguayan striker had been bought from Argentina's Independiente for £6.9 million in 2002, and it took him 27 games to score his first goal, making him another in a rich heritage of failed strikers at United - precedents include Garry Birtles, Nigel Davenport, Dion Dublin and Alan Brazil. He had averaged nearly a goal every two games for Independiente as they twice won the league but he took a while to settle and adjust to the pace of the game in England. One of his problems was playing alongside Ruud Van Nistelrooy - an awesome poacher and goalscorer, but also a player who needs an entire team's play to revolve around his game (which is one reason Sir Alex Ferguson sold him once it became clear Rooney and Ronaldo were the players he should build a team around). Forlan then was more of an old-fashioned inside right; with the ability to take the ball off the midfield and run at defences, able to shoot with either foot and slip passes to other attackers. He worked hard to make himself more of a European striker and improved his movement in the box. In the Championship winning year of 2002-03 he scored some crucial goals and earned himself a lifelong place in United cult fandom by scoring two against Liverpool at Anfield. But United's purchase of Rooney made him surplus to requirements, having scored only 10 goals in 63 games. For Villarreal, he would notch 54 in 106, and for Atletico Madrid, 64 in 97, suggesting that we never quite saw the best of him in England, though United fans could always see that he was a class act; just not the right class act at that time.
Jari Litmanen - Liverpool
It often seemed during the Evans and Houllier eras that Liverpool really needed a Cantona figure. Somebody to tie it all together, a genius to make the difference in the tightest games, that spark, something out of the ordinary. Preferably a foreigner, an unknown quantity in Britain. Litmanen was meant to be that player.
He had been one of the hottest players in World football after a magical spell at Ajax, where he wore the totemic Number 10 in Louis Van Gaal's European Cup winning team. He was a playmaker but a great goalscorer too, topping the Dutch scoring charts in the 93-94 season. He began moves with visionary passes and then arrived in the box to finish them off. Had he not been unfashionably Finnish, he would possibly have been voted World Player of the Year at that time. He was that devastating. He followed Van Gaal to Barcelona in 1999 but played little over two seasons as he was frequently injured, setting a pattern that would continue for much of his playing career. It certainly continued at Liverpool after he was signed by Houllier on a free transfer in 2001. He only lasted a season, playing 21 times, and it quickly seemed that even when he was fit Houllier didn't quite trust him or use him enough. He scored 5 goals and donated a few match-changing performances, but it wasn't quite enough, and having missed out (through injury, of course) on all three of the Finals Liverpool won at the climax of the 2000-2001 Season, he returned to Ajax in August 2002.
Andriy Shevchenko - Chelsea
In his pomp at Milan Shevchenko was unequivocally the greatest striker in European football. But at Chelsea, after Roman Abramovich had pursued him for years and spent a large amount of money to prise him away from Silvio Berlusconi, he looked a shadow of that player. He scored 127 goals in 208 games for AC Milan. He won a scudetto or two, a European Cup, and European Player of the Year. He was awesome and feared across the continent. He scored tap-ins and headers, thunderbolts from distance, placed finishes. Chelsea paid £30.8 for him in May 2006, and altough the goals never quite dried up, he was never the same. Overshadowed by Didier Drogba, seemingly not trusted by Jose Mourinho, and most crucially, lacking that burst of pace which had allowed him to arrive in the right pace at the right time more often that most strikers, he never seemed to settle at Chelsea. He scored here and there, even some significant goals, but he never shone the way the player from Milan had, was never the talisman his price-tag demanded he be. His second season was blighted by injury and after a third, he was loaned back to Milan and eventually sold back to Dynamo Kiev, the club where he had originally broken through.
Nelson Vivas - Arsenal
Arsene Wenger has never really had much of an eye for a defender. Attacking football is obviously never a problem. But defense? Consider that he arrived at Arsenal to find that legendary back four already in place and that over the next decade he attempted to replace them with the likes of Stepanovs, Luzhny, Cygan and Grimandi. His best defensive purchases have been lured from clubs right under his nose - Sol Campbell from Spurs and William Gallas from Chelsea. Then there is Nelson Vivas. He had a solid early career in Argentina - seven years with first Quilmes and then Boca Juniors, followed by a 1997 loan to Switzerland's AC Lugano. Arsenal bought him after only a Season there with a view to replacing Lee Dixon at right back. He played games that first Season, but was never quite a regular as Wenger juggled him between fullback positions and his struggle to cope with the Premier League's pace meant that he made a lot of late tackles and received sundry yellow cards. His willingness to attack also proved something of a weakness, given his inability to match the pace of the games around him.
His second season was affected by his injury problems and, altough he had a small cult among Arsenal fans for his strength and bravery, his fate was already sealed by the club's purchase of Luzhny. Here is a player who should have been to Arsenal what Gabriel Heinze would be to Manchester United - an Argentine Warrior-defender, committed, driving, courageous and technically adroit. Instead his career in England drifted away from him and he was sold to Inernazionale in 2001 after a Season's loan at Celta Vigo. He played 39 times for his country.
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