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Football transfers: Biggest flops in the last 20 years

A look at five deals which definitely did not work out

(From L-R) Philippe Coutinho, Arda Turan, Eden Hazard and Romelu Lukaku

The 2023 summer transfer window is well and truly underway. Jude Bellingham joined Spanish giants Real Madrid for a fee in excess of €100 million. English club Arsenal have, reportedly, finalised the £100-million-plus deal for Bellingham's midfield compatriot Declan Rice. Real are also still said to be pursuing Kylian Mbappe. If that deal happens (unlikely) it well could beat the world record transfer fee—€222 million—paid by Mbappe's current club Paris Saint-Germain for Neymar in 2017.

Apart from Bellingham, a major deal which was completed in June was Kai Havertz to Arsenal for a fee in the region of £65 million. This was intriguing as, Havertz, once counted among the brightest prospects in world football, had a difficult 2022-2023 at Chelsea. But, Arsenal manager Mikel Arteta is clearly confident that he can bring the best out of the 24-year-old German. Then again, football managers, even the best like Sir Alex Ferguson and Pep Guardiola, have made bad signings. It remains to be seen whether Havertz goes down as a mistake by Arteta. 

For now, below is a look at five deals from the past two decades which definitely did not work out:

Juan Sebastian Veron, Chelsea

The former Argentine midfielder is perhaps better known as a Manchester United flop. But, he was even worse for Chelsea. He moved to United in 2001 for a then British transfer record of around £28 million. He started well, but faltered as the season progressed. Ferguson defended him fiercely, even calling journalists who questioned his performances, “f*cking idiots”. His performances improved in the second season, though he still fell short of meeting expectations. 

However, newly cash-rich Chelsea had seen enough to buy him for £15 million in 2003. Manager Claudio Ranieri said he was the best midfielder in the world, but he played only 14 times (scoring once) in his debut campaign, partly because of injuries. And that would be the end of his Chelsea career—in comparison, he had played 82 times for United in two seasons and made 26 goal contributions (goals and assists). He was contracted to Chelsea from 2003 to 2007, but was loaned out from 2004 onwards. To add insult to injury for Chelsea, he rediscovered his form while on loan and won three major trophies in two years with Inter Milan (2004-2006) and, in the 2006-2007 season, starred as his boyhood club Estudiantes won a first Argentine title in 23 years. He left Chelsea the following season to join Estudiantes for free. 

Arda Turan, Barcelona

The Turkish winger was going places before his move to Barcelona. He had joined Atletico Madrid from Turkish giants Galatasaray in 2011, aged 24. He played about 45 games a season across four years at the club and was a key cog in the team that pipped Barcelona and Real to the Spanish league title in 2013-2014. The team also reached a Champions League final for the first time since 1974 (lost to city rivals Real), and had won the Europa League in 2011-2012 and the Spanish Cup in 2012-2013. This meant that Turan had three major trophies with Atletico in four seasons. When he agreed to sign for Barcelona in 2015—Atletico let him go for a fee of €34 million, plus €7 million in variables—it seemed like the logical next step. There was a small issue—the Catalan giants were under a transfer ban. As a result, Turan could be registered as a player only after six months. So, from July 2015 to January 2016, he sat on the sidelines. Turan would never be the same again. 

His skill and vision were intact when he started to play for Barcelona, but he seemed to have lost the tenacity and invention that set him apart during his spell at Atletico. He played 25 times in that first half a season, then 30 times in the entirety of the next season and, in his third season, he, shockingly, did not play once in the first half. So, he was loaned out to Istanbul Basaksehir for the remainder of the season. The loan deal was extended for two more seasons and Turan then left Barca as a free agent to return to his boyhood club Galatasaray.

Philippe Coutinho, Barcelona

When Barca decided to splash that Neymar cash in January 2018, they brought in the Brazilian attacking midfielder for a fee believed to be around €135 million, including add-ons. Contrary to popular opinion, he had some decent games for the club. But, it is still among the worst signings of all time, especially because his best performance during his four and a half year stay at the club, arguably, came against Barcelona as he came off the bench to score a brace in the club's 8-2 demolition by Bayern Munich who had loaned Coutinho for the season.

Overall, Coutinho played 106 times for Barcelona, scoring 25 and assisting 14. Those numbers may not look too bad, when considered in isolation. But, the transfer fee and the expectations around Coutinho's arrival make them look criminally bad. He joined Aston Villa for a fee of €20 million in 2022.

Eden Hazard, Real Madrid

If anyone can make Coutinho look good, that is the Belgian legend. He joined Real in 2019 for a fee that could be as much as €145 million because of add-ons. He was in the Spanish capital for four years and played a shockingly low 76 games (seven goals and 12 assists). He left recently as a free agent and is without a club as of June 30.

There is arguably no one else in world football today who can match Hazard's drastic decline. When Real signed him, he was among the best five players in the world and despite his torrid time in Madrid, he is still considered to be among the best wingers of his generation. Hazard suffered a horror tackle by his Belgium colleague Thomas Meunier while playing against PSG in the Champions League in his first season for Real. He missed 16 games across competitions and was never able to produce his best for Real, having been pushed to the periphery because of the rise of Vinicius Jr.

Romelu Lukaku, Chelsea

We are back were we started with Chelsea. But, that is only natural since the Blues have had two separate spells of “new-found” wealth in the last 20 years. Lukaku, the most expensive player of all time in terms of cumulative transfer fees, was almost always at risk of being labelled an overpriced flop. But, remarkably, he managed to do just about enough to avoid that tag for 12 years of his senior career. That is until 2021, when he chose to return to Chelsea for a second stint. The blues had first signed him for €15 million in 2011 as an 18-year-old. They sold him for around €35 million in 2014 and bought him again for around €115 million seven years later. 

Lukaku's return, after two excellent season for Inter Milan, caused much excitement and he was even described as the final piece of the jigsaw for Chelsea. It was said at the time that he could deliver the Premier League title for Chelsea. He did not. He played 44 games, scored 15 goals and assisted two. Then, in the 2022-2023 season, he went back on loan to Inter and got to the Champions League final. His contract at Chelsea is till 2026 and the club is desperately trying to offload him, but there is no mad scramble to buy him. Inter offered another loan deal and was dismissed by the London club. Now, Lukaku is being linked to a move to Saudi Arabia. If Chelsea pull that off, they may be able to recoup some of their investment and but the big Belgian still has be to get an F.

Dishonourable mentions

Coutinho, Hazard and Lukaku, to an extent, suffered from inflated transfer fees. It was not their fault that clubs overpaid, but the modern footballer will inevitably be judged by the price tag. As a result, some players from before the inflated transfer fee regime of recent years missed out, or rather, were spared, from this list. For instance, El-Hadji Diouf, Senegal's 2002 World Cup hero, who signed for Liverpool soon after the tournament in Asia. He was an absolute disaster—six goals in his first season and none in his second, and, he kept spitting at opponents and opposing fans.

Brazilian Julio Baptista and Italian Antonio Cassano were both signed by Real during the 2005-2006 season. Baptista, a big-money signing, was played out of position and was ineffective. Cassano was an absolute steal as a result of a breakdown in his ties with his former club Roma. It seemed like the gifted Italian, who looked unstoppable at Roma, would prove to be one of the smartest signings in the illustrious history of Real Madrid. He was not. Within months of arriving in the Spanish capital, he was visibly overweight, he was accused of drinking heavily and being disrespectful. He also told a Madrid radio station that he was willing to walk back to Rome. 

Two of Chelsea's British record signings—Andriy Shevchenko (2006) and Fernando Torres (2011)—underwhelmed. So did Andy Carroll, who Liverpool replaced Torres with. Also worth a mention is Alex Song's move to Barcelona in 2012 and Roberto Soldado's transfer to Tottenham Hotspur in 2013.