Top 20 Biggest Transfer Flops in World Soccer

Transfer season marches forward as the summer moves along. Every day we run to use the internet, check in on twitter or talk to co-workers about the latest rumors, gossip and player moves. For the most part, we get giddy when we catch a rumor that our club is linked with a notable name – perhaps a recently discovered gem from this summer’s World Cup or a player out of contract at another club? It all makes for an equally exciting and nerve wracking period for football fans. Come the end of the summer, the transfer window will shut and we will all take stock of what our respective teams have accomplished while enviously trying to figure out how well the other clubs have done.

Of course, signing a bunch of new players can be a bit of a gamble. Every now and then a player will have a breakthrough and become a real star of the club. More often than not, new players will be okay, do about what you expected from them and eventually move on in a few years. Then there are the duds. In every window we are treated to footballing flops. These are the players who force us to put our faces in our hands or (if they are on the opposition) point and laugh at the on and off-field hilarity.

The topic of footballing flops is a subjective one. Fans of a club rarely like admitting their team has bought a lemon. Owners and managers like it even less. There have been so many terrible transfers over the past decades that odds are your club has seen its share of transfer flops. The following list looks at 20 of the biggest flops in no particular order. In most cases, these flops failed to live up to past performances or expectations placed upon them. A striker who stopped scoring goals, a midfielder who had an amazing World Cup only to follow it up with mediocrity, a player who dominated one league only to vanish when transferred to another – these are all flops. Other players listed here simply did not live up to ridiculous price-tag attached and, therefore, qualify for ‘flop’ status.

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19 Alfonso Alves – Heerenveen to Middlesbrough

via sportsmole.co.uk

From 2006 to 2008, Brazilian striker Alfonso Alves made a name for himself by scoring 45 goals in 39 games for Dutch side Heerenveen. That was good enough for Middlesbrough to sign him for an estimated $21 million in January 2008. He made a total of 47 appearances in a year and a half and scored 13 goals. Disappointing league production led to the decision to sell Alves. In 2009, he moved on to Qatari League club Al-Sadd for about half of the fee Middlesbrough had originally paid for him.

18 Denilson – Sao Paulo to Real Betis

via onfootball.co.uk

One of the promising talents to come out of Brazil in the late 1990s, Denilson gained fame thanks to a number of good performances for Brazil and his club team, Sao Paulo. It was enough to convince Real Betis, who signed the winger for a then world record transfer fee of $37 million. Seven years with Real Betis, including one loan spell, saw Denilson score just 16 league goals in 197 appearances. He moved onto Bordeaux which began a series of free transfers where he only ever scored a few goals before moving on to a new club.

17 Stewart Downing – Aston Villa to Liverpool

via theliverpoolword.com

During the 2010/11 EPL season, Stewart Downing scored seven goals and notched nine assists with Aston Villa. Liverpool saw real potential in the English midfielder and paid $32.8 million for his signature in July 2011. For the next two seasons, Downing made a total of 65 appearances for the Reds and only managed to score three goals and create five assists – a far cry from his production at Aston Villa. In 2013, Liverpool cut their losses and sold Downing to West Ham for a fee in the region of $8.4 million.

16 Keirrison – Palmeiras to Barcelona

via fcbarcelona.com

Brazilian striker Keirrison was supposed to be another one of those ‘next-big-things’ when it came to football. He developed his trade at Brazilian sides Coritiba and Palmeiras before moving to Barcelona in 2009 for $21 million. Officially a Barcelona player from 2009 to 2014, Keirrison never played a first team match for the club. Instead, he spent the entire time being loaned out to clubs like Benfica, Fiorentina and Santos where he played a handful of games each season and scored a few goals. This past March, Keirrison agreed to return to Coritiba on a free transfer once his Barcelona contract expired July 1st.

15 Shaun Wright-Phillips – Manchester City to Chelsea

via thesun.co.uk

Heading into the 2005/06 EPL season, midfielder Shaun Wright-Phillips was one of the most exciting and anticipated transfer breakthroughs. Manchester City’s Young Player of the Year four times, the speedy winger scored 10 goals in 34 appearances in his final season in Manchester. For $34.5 million, many believed Chelsea had bought a great player who would tear opposition defenses wide open. It was not to be. In 81 appearances over three seasons, Wright-Phillips managed only four goals. In August 2008, Chelsea sold him back to Manchester City for around $14.3 million.

14 Ricardo Quaresma – Porto to Inter Milan

via ilgiliforum.com

Between 2004 and 2008, Portuguese winger Ricardo Quaresma demonstrated his potential by scoring 30 goals in 156 total appearances for F.C. Porto. Naturally, this attracted the attention of European giants, including Inter Milan. In September 2008, Quaresma signed for the Italian side for a hefty $33 million. Big things were expected and everyone was disappointed (with the exception of Milan fans) when the player failed to live up to expectations. Inter’s newest ‘star’ scored a single goal over the following two seasons which included a loan spell at Chelsea.

13 José Antonio Reyes – Sevilla to Arsenal

via arsenal.com

In January 2004, Arsenal added to their already potent strike-force with the signings of Spanish forward José Antonio Reyes from Sevilla. The $27.5 million transfer was steep but Arsenal hoped they had uncovered a gem who had already managed 21 goals in three seasons in La Liga. Reyes managed 16 goals in three seasons at Arsenal. Home-sick and unable to adjust to London, the forward was loaned to Real Madrid in exchange for Julio Baptista in 2006 and subsequently sold the following year to Atletico Madrid for a fee of $16 million.

12 Juan Sebastián Verón – Lazio to Manchester United

via caughtoffside.com

Verón had enjoyed great success with Parma and Lazio, winning domestic cups, the league title and even the 1999 UEFA Cup. United’s coach, Sir Alex Ferguson, believed the Argentinian midfielder would be perfect for his attack and so La Brujita (Little Witch) made his move from Serie A to the Red Devils of the EPL in 2001 for $46.1 million. It never really worked out as Verón managed only seven goals in 51 games. The team decided to cut their losses and sold the midfielder to Chelsea for $24 million in 2003. The Little Witch struck again as Chelsea quickly realized they too had bought a lemon.

11 Djemba-Djemba / Kleberson – Nantes and Atletico Paranaence to Manchester United

via unitedbanter.blogspot.com

Our first two for one deal; and it wasn’t much of a deal for Alex Ferguson and Manchester United. From 2003 to 2005, United fans had to watch Cameroonian Eric Djemba-Djemba and Brazilian Kleberson run around the midfield and accomplish little. Combined, the two cost around $16 million – a bargain compared to some on this list – but gave back very little. Over two seasons each player scored 2 goals in 20 games. Both were sold on for around half of what they cost United in the first place. The going joke is that Djemba-Djemba was so bad they named him twice.

10 Robbie Keane – Tottenham to Liverpool

via theguardian.com

Robbie Keane is a bit of a strange one as far as flops are concerned. From 2002 to 2008, he did well at Tottenham, scoring 82 goals in 197 appearances. Then, in 2008 he made the move to Liverpool for a fee of $33 million. We’re pretty sure management at Anfield checked his ID after every game because the Irish striker in no way performed as well once he joined the Reds. Seven goals in 28 total appearances was not good enough and Keane was shipped back to White Hart Lane after only half of a season for around $25 million.

10. Diego – Werder Bremen to Juventus

via uefa.com

Having played for Santos and Porto, attacking midfielder Diego furthered his reputation during his three years at Bundesliga side Werder Bremen. He quickly gained a reputation for being an all-round excellent player who could score and assist. His blend of skill and goal-scoring attracted many eyes. In 2009, Juventus hoped to get a boost with the signing of the Brazilian-born star for a fee of $37 million. Diego did not fit in with Juve’s fans or style of play. In his only full year with the club (2009/10), he scored seven goals in 44 appearances.

9 Tiago Mendes – Lyon to Juventus

via tuttosport.com

Really, this could go down as a Chelsea flop, but since we are on the topic of Juventus, let’s stay there. Portuguese midfielder Tiago Mendes did well over 2002-2004 with Benfica where he scored 24 goals in 86 appearances in all competitions. Chelsea took a gamble and lost, with Tiago netting four goals in 47 appearances. Juventus failed to heed the warning and signed the midfielder in 2007 for $21 million – roughly $3 million more than Chelsea had paid. Juventus may have paid more but they got even less with Tiago scoring no goals in 48 appearances in all competitions.

8 Robinho – Real Madrid to Manchester City

via tuttosport.com

In 2008, Manchester City were purchased by the Abu Dhabi United Group which gave the club massive sums of cash to spend. City went out and threw money at any player they wanted, hoping to attract top level talent. Real Madrid forward Robinho took notice and made the move for $54 million. Despite thinking he was going to Chelsea, the Brazilian did well at first and scored 14 goals in 41 games. Production rapidly dropped off after that. Decreased appearances and an eventual loan move signaled the end of his EPL career. In August 2010 his move to AC Milan was completed for $25.3 million.

7 Erik Lamela / Roberto Soldado – Roma / Valencia to Tottenham Hotspur

via fourfourtwo.com

In the summer of 2013 Tottenham Hotspur sold Gareth Bale to Real Madrid for around $140 million. The North London club then proceeded to spend the money like one of the housewives of Orange County. For a combined $90 million, the club purchased Erik Lamela and Roberto Soldado from Roma and Valencia respectively. At first, it appeared the club had got two great players. Midfielder Lamela had scored 21 goals in two seasons with Roma and Soldado had netted 81 times with Valencia. At Tottenham, things have been different. Lamela has managed only one goal all last season while Soldado only scored twice from open play in the league. Things may change but it will need to be fast and drastic if these two are to shake off the ‘flop’ label.

6 Fernando Torres – Liverpool to Chelsea

via skysports.com

Torres moved from Liverpool to Chelsea in January 2011 for $82 million. El Nino, as he is nicknamed, was pricey but had proven himself at Anfield with 81 goals in 142 appearances over four years. On paper, he gave Chelsea’s attack a killer edge over most other teams. Unfortunately, the Spaniard’s time at Stamford Bridge has not been what most thought it would be. In 172 appearances over four years he has managed just 45 goals. Despite this, the fans continue to stand by their striker while others have not.

5 Nicolas Anelka – Arsenal to Real Madrid

via chelsearus.com

Known unofficially as ‘Le Sulk’ because of his propensity to pout and get upset when he didn’t get his way, Nicolas Anelka has played for a dozen teams over his career. It all really started at Arsenal where the French striker showed his pace and shooting skills. He scored 19 goals in 46 appearances for the Gunners. Naturally the big Spanish clubs came calling and Real Madrid signed Anelka for $37.6 million in the summer of 1999. As with any club Anelka has gone to, he soon fell out of favor with everyone. Before being shipped off to PSG for nearly what Madrid had originally paid, Anelka’s one season in the Spanish capital saw him score 7 goals in 33 total appearances.

4 Andriy Shevchenko – AC Milan to Chelsea

via ynaija.com

If ever there was a signing of intent, the 2006 purchase of Ukrainian Andriy Shevchenko was it. The striker had made his name at AC Milan, scoring 175 goals over seven years. Chelsea decided to break the English transfer record and signed the goal-machine for $50.5 million. Everyone eagerly watched and waited for Shevchenko to tear teams apart and rack up the goals. It never happened. The striker managed only 22 goals in 77 appearances over two full years while at Stamford Bridge. He was loaned out to AC Milan before rejoining Dynamo Kiev after being released from his Chelsea contract.

3 Jonathan Woodgate – Newcastle United to Real Madrid

via sportsmole.co.uk

From 1998 to 2004, Jonathan Woodgate built a reputation as a good defender. He also had a reputation for getting injured – something Real Madrid either missed or hoped would go away under the warm Spanish sun. In any event, the La Liga giants signed the Englishman for $24.5 million in August 2004. He didn’t play a single game the entire first season and managed only 14 matches in his second season with Real Madrid. Not a lot of people in England were genuinely shocked by this. In a poll by sports paper Marca, fans voted him the worst signing of the 21st century.

2 Kaka – AC Milan to Real Madrid

via soccerball365.com

Not a name you generally associate with failure, but Kaka’s time at Real Madrid was anything but a success, especially when compared to his time at AC Milan. With the Italian club, the Brazilian midfielder had shone, scoring 95 goals in 270 appearances in all competitions. In 2009, Real Madrid secured Kaka’s signature for a then record of $94 million. The Brazilian could not live up to the price-tag, nor replicate the form that had made him so deadly at Milan. Over the following four seasons with Real Madrid, Kaka could only muster 29 goals and 120 total appearances. In 2013 he returned to Milan on a free transfer and has now moved to Orlando City.

1 Andy Carroll – Newcastle United to Liverpool

via telegraph.co.uk

Liverpool found out the hard and expensive way that a player’s performance at one club doesn’t necessarily carry over to a new club. Andy Carroll was purchased in January 2011 following the departure of striker Fernando Torres. The Reds had $80 million from the sale of Torres and sought to find a replacement immediately. They bought Andy Carroll from Newcastle for $57.4 million. The big English striker had 11 goals in 20 appearances for Newcastle in the 2010/11 season. Over the next two-and-a-half seasons with Liverpool, he only managed 11 goals in 58 appearances. In 2013, Carroll made a permanent move to West Ham United for a fee of around $24 million.

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