It is remarkable, really, how seductive transfers remain to the average football fan. There is an entire industry devoted to coverage of employment changes in the sport and a good portion of its followers who take more interest in possible moves than the actual matches.
It is remarkable, really, how seductive transfers remain to the average football fan. There is an entire industry devoted to coverage of employment changes in the sport and a good portion of its followers who take more interest in possible moves than the actual matches.
All of this despite the overwhelming evidence that most incoming players do not significantly improve a team in the long run. Sometimes it is far worse than that.
The cautionary tales below are littered with hubris, profligacy and wishful thinking. They should be enough to dissuade any panicky clubs from spending big for the sake of it in the days that remain of this transfer window. If not, directors of football should at least pay heed to the lessons which each of these examples provides.
We have limited our list to incomings to the English game, so no room for Philippe Coutinho to Barcelona, or selling clubs making a terrible mistake, like Leeds letting Eric Cantona go to Manchester United. Not to worry, Manchester United will still feature, but we begin with the club that sold the Frenchman.
10. Tomas Brolin
£4.5m, from Parma to Leeds, 1995
Was bought to pull the strings for Tony Yeboah from midfield but injury issues in the squad meant he started up front, then was shunted out wide. Did not take kindly to the defensive work that entailed and had a series of falling outs with Howard Wilkinson, before going on loan to FC Zurich. Came back hoping for a new start under George Graham but, in Brolin’s words in 2012, he was “an even bigger idiot”. Managed only 19 games and, to put it kindly, did not often look in peak physical condition.
Lesson Make sure your scouts research the personality as well the player.
9. Andy Carroll
£36m, from Newcastle to Liverpool, 2011
Fernando Torres, in a move which narrowly missed this top 10, joined Chelsea on deadline day in January 2011. Carroll inherited his No 9 shirt at Liverpool, but did not find it imbued with magical Billy’s Boots-style goalscoring powers. Brendan Rodgers wondered if his tactics had hindered Carroll, but 11 goals in 58 games backed up the visual evidence that he was short of the quality required. Fortunately, in the same window Carroll arrived, Liverpool also signed Luis Suárez.
Lesson You may not always be thinking clearly when trying to replace one of your best players in a hurry.
8. Stéphane Guivarc’h
£3.6m, from Auxerre to Newcastle United, 1998
Played all but one game in France’s victorious World Cup of 1998, but did not score a goal. That was enough for Kenny Dalglish to bring him to Tyneside, where he managed one goal in four appearances before being sold to Rangers for a £1m loss three months later. As observed by Chris Bascombe in these pages, he left Newcastle “with as many apostrophes to his name as goals”. The Daily Mail once named him the worst striker in the history of the Premier League, Guivarc’h responded by saying: “It is truly a c--- newspaper.” Let’s hope he is not a Telegraph subscriber.
Lesson Never sign players on the basis of one good international tournament.
7. Steve Daley
£1.44m, from Wolves to Manchester City, 1979
Briefly, quaintly, the most expensive player in England, until Andy Gray moved from Aston Villa to Wolverhampton Wanderers a week later for Daley’s fee plus £25,000. Daley had been a goalscoring midfielder for Wolves, but never got going at City. Manager Malcolm Allison claimed he only wanted to offer £400,000 but Peter Swales did the deal for a million more. Swales always denied it and the fee was not Daley’s fault, but weighed him down. His name was inevitably brought up in transfer misstep conversations for years. Was sold to the Seattle Sounders, in a time when that was an even more demoralising move than it would be today.
Lesson Agree your budget for a transfer bid in writing, ideally witnessed by a lawyer.
6. Mykhailo Mudryk
£62m, from Shakhtar Donetsk to Chelsea, 2023
Forget the doping charge which could keep him out of English football for a further four years, Mudryk was already a calamitous signing. Chelsea hijacked a proposed move to Arsenal early in their trolley-dash approach to squad-building under Todd Boehly and friends. It was seen as a coup, but quickly looked like a bullet dodged in north London. In his first season Mudryk showed occasional glimpses of talent, roughly enough for a three-minute YouTube compilation. It was nowhere near enough to vindicate his enormous fee and his reputation was not helped when then manager Mauricio Pochettino revealed Mudryk was unable to beat him in their training crossbar challenges.
Lesson Snatching a player from a rival does not make them any more likely to succeed.
5. Francis Jeffers
£10m, from Everton to Arsenal, 2001
Arsène Wenger’s renard dans la boîte (if he bothered to learn our idioms the least we can do is Google translate them back into French) who joined a team already featuring Thierry Henry, Nwanwko Kanu, Sylvain Wiltord and Dennis Bergkamp. One of these things is not like the other. Eight goals in 39 games does not sound a bad return, except that was not his first season in London, but his entire three-year stay. “I was out partying, living life, tossing it off in training because I always thought I wouldn’t play Saturday anyway,” he said, somewhat sadly, in 2014. For a million pounds more on the same day Chelsea bought Frank Lampard.
Lesson Sometimes more strikers are not necessary.
4. Alexis Sánchez
Free, from Arsenal to Manchester United, 2018
It would not be hard to fill a top 10 of dubious transfers with Manchester United acquisitions of the last decade. One more will come later in this list, but few have been as significant as the Chilean’s move to Old Trafford. Admittedly United did not pay a fee, but they certainly made up for it with his wages, £560,000 per week. Saudi Pro League money for a Sunday league return: two goals in 27 matches in his only full season. It had been 30 goals in 51 for Arsenal the previous season. Oh well, at least everybody enjoyed the grand piano signing video. Focus on that rather than the obliterated wage structure.
When Sánchez signed for United, even the piano intro had more views than some movies 🎹🎬 Unreal era. pic.twitter.com/43Bj6oqeXN
— O.T Ace (@AceOfOT) August 21, 2025
Lesson Beware buying at the top of the market.
3. Jo
£19m, from CSKA Moscow to Manchester City, 2008
Signed shortly before the big money arrived at City for a club-record fee. “He’s a big talent and a young man with a big future,” Mark Hughes, manager at the time, said. Big future turned out to involve a loan move to Everton the following season. Managed only one goal in 21 appearances for City, and was also partially responsible for his compatriot Robinho’s decision to make another expensive and disappointing move to Manchester in the same window.
Lesson Being Brazilian does not guarantee excellence.
2. Winston Bogarde
Free, from Barcelona to Chelsea, 2000
Became the spirit animal for the modern Premier League mercenary for his near-four year stint as a mostly unused defender. He was paid a then-astronomical £40,000 per week, earning £8.24m in total over his time at Chelsea. That equated to £686,666 for his nine league appearances. Claimed later he was hampered by Chelsea’s refusal to consider loan moves which would only have covered a portion of his salary. It is worth restating that Bogarde did nothing wrong in opting to take the salary he had been promised. Still goes down as a horrendous waste of money, talent and time.
Lesson Try not to be anyone’s last big pay day.
1. Antony
£85.5m, from Ajax to Manchester United, 2022
The perfect summary of most of the themes already touched upon in this list. A vast overestimation of talent from a limited sample size in a questionable league, a gross overpayment and a total inability to deliver. In a previous era underperformance after a big-money move became funny rather than shameful quite quickly. That is fine when Kleberson does find his feet after costing £6.5m. Less funny when the player in question cost £30m more than United had hoped to spend, and was the fourth most expensive player in Premier League history. May yet revive himself as his exit nears, probably to Real Betis. This will not change his status as the worst buy in English football history.
Antony does a spin but cannot complete the pass 37".
byu/keithohara insoccer
Lesson Do not give your manager everything he asks for. Especially if he has not been in the job for very long, and may not be for much longer.
Category: General Sports
