Premier League clubs, and other teams around the world, use the summer and January transfer windows to improve their squads and, in some cases, turn profits via the sales of players. Many of the transfers work out well for both sides involved. In the summer of 2017, Tottenham Hotspur cashed-in on the sale of right back Kyle Walker. Meanwhile, City landed a player who helped the club win the EPL title. While one would have to assume Tottenham boss Mauricio Pochettino probably would have preferred to keep Walker in his team for the 2017-18 season, odds are that Pochettino has welcomed the next challenge that involves building up a different member of the squad.
Just like with free agency signings and trades in sports leagues from North America, not every EPL transfer works out for both teams involved in that transaction. Some teams feel regret a year or two after those moves are made, to the point that those clubs cut ties with the players in order to get some value, money in most instances, following those failed experiments. In fairness to every player spotlighted in this piece, some players require several seasons to make impacts with teams following transfers, especially if those individuals move to different countries. Some transfers aren’t all that different than a person taking a chance on a stock. One bad decision can cost a manager millions of dollars and, in extreme instances, his job.
20 Moussa Sissoko to Tottenham Hotspur
For reasons that make little sense to passionate Tottenham supporters, manager Mauricio Pochettino remained keen on picking Moussa Sissoko throughout the 2017-18 campaign even though Sissoko routinely gave the ball away and failed to come close to hitting the back of the net. Spurs buying Sissoko in August 2016 appeared to be a panic acquisition at the time, and it now seems like it would be best for all involved if the club could sell him ahead of the start of the 2018-19 season. Odds are the club won’t recover the money spent on him in the original transfer, but that’s a risk Tottenham have to take while the summer transfer window is open.
19 Kevin Wimmer to Stoke City
Tottenham have made multiple regrettable transfers over the past couple of years, but selling defender Kevin Wimmer to Stoke City was a good bit of business for Spurs. Stoke, meanwhile, likely feel differently about the move. Wimmer failed to improve while with Spurs, so much so that the club prepared itself to take a financial hit regarding his future after Stoke were relegated. In May 2018, it was announced that Wimmer had been sent on loan to Bundesliga club Hannover 96, with the potential that he could join that side on a permanent transfer. Stoke likely will be hoping Wimmer is a hit for his new team so that the club can recover some cash.
18 Zlatan Ibrahimovic to Manchester United
The signing of striker Zlatan Ibrahimovic in July 2016 was not the problem for Manchester United. Retaining Ibrahimovic up through the start of the 2017-18 campaign is where this becomes a regrettable transfer for the club. By that time, it was clear that the two entities were headed in different directions, and there were already rumors that Ibrahimovic wanted to “dare to Zlatan” in the United States as part of the LA Galaxy before he and United parted ways. Ibrahimovic accepted a generous cut in wages to complete that switch, but it is assumed his camp believes money can be reclaimed via sponsorship deals and other opportunities.
17 Ross Barkley to Chelsea
It is still early days into this transaction, but it sure appears as if Chelsea swooping in to acquire Ross Barkley from Everton in January 2018 largely so that he could not make a move to Tottenham was a petty transfer that the club may regret. While Barkley is only 24 years old and, theoretically, could still have plenty of time to make an impact at Stamford Bridge, it is difficult imagining him finding a long-term spot in the team not knowing what is to come regarding the club’s manager and future. Perhaps Antonio Conte’s replacement, whoever that will be, will be keen on giving Barkley a spot in the starting XI; probably not, though.
16 Joe Hart to West Ham
We understand why West Ham took a flier on goalkeeper Joe Hart via a loan in July 2017. While Hart was no longer what he was during his best days with Manchester City, the EPL side likely hoped he would recover at least something resembling his old form. It didn’t happen. By now, the book is out on how to beat Hart, and the 31-year-old probably is not fixing those visible flaws in his game at this point of his career. Hart, left out of the England World Cup squad as just about everybody expected, could remain in England by completing a transfer to relegated West Brom ahead of the 2018-19 season.
15 Guido Carrillo to Southampton
Southampton avoided relegation in the spring of 2018, but few will credit striker Guido Carrillo for the team remaining in the top flight. The front man who joined the club in January 2018 failed to hit the back of the net with the EPL side, and the 27-year-old will likely have to stay put if only because the club would not be able to get equal value for his services following the first several months of his stint with the team. Carrillo will have an entire offseason and summer to prepare for life in the Premier League. Perhaps that will help him turn things around and remove his name from lists of the worst EPL transfers in recent memory.
14 John Stones to Manchester City
Perhaps the best description one has come up with for defender John Stones is that he “looks like a Rolls Royce with exhaust problems,” as Joe Bernstein of the Daily Mail put it. When Stones made the expected move from Everton to Manchester City in August 2016, that hope was that he was beginning his evolution toward becoming one of the better central defenders for country and club. That hasn’t happened, as he has often appeared unsure of himself on the ball and been a liability in defense. Suffering an injury knock in the World Cup could represent yet another step in the wrong direction as it pertains to his career.
13 Jese to Stoke City
PSG forward Jese joined Stoke City from Paris Saint-Germain on a loan in August 2017, he introduced himself to his new fans by scoring a goal in his debut, and he then essentially fell off the face of the earth. By the time April 2018 arrived, Jese was making headlines for failing to report to the club after he was granted compassionate leave to care for his son. In May, Stoke granted him unpaid leave, which officially ended one of the worst transfer decisions made by an EPL side in recent memory. Stoke were relegated from the Premier League days after the club officially parted ways with Jese.
12 Loic Remy to Crystal Palace
Striker Loic Remy was once reportedly sought after by multiple Premier League outfits, but he was a disappointment throughout his stint in the EPL. Most recently, Crystal Palace learned that Remy simply could not get the job done or score goals with regularity in the league. When he returned to Chelsea in the summer of 2017, the club handed him an outright release. Las Palmas elected to give him a chance, but that club sent him on loan to Getafe in January 2018. Unless something changes in his career path or a club wants to do him a favor and pay him, the 31-year-old likely will never again play in the Premier League.
11 Gylfi Sigurdsson to Everton
Everton attempted to buy their way into a seat at the European football table with multiple transfers, including the purchase of Gylfi Sigurdsson in August 2018 after the club pursued him for a considerable amount of time. Sigurdsson failed to find the success he enjoyed while with Swansea City, although defenders of the player would say that Everton’s lack of a reliable striker up front prevented Sigurdsson from being all that he could have been during his first season with the club. He is set to return to Everton following the World Cup for what he hopes will be a better campaign than what he endured throughout 2017-18.
10 Paddy McNair to Sunderland
It almost feels as if Paddy McNair is the answer to a trivia question about somebody who was once advertised to be a Manchester United prodigy but who never took the next figurative step toward greatness. McNair completed a transfer from United to Sunderland ahead of the 2016-17 season, but he failed to become all the Black Cats needed him to be largely because of injury woes. In late June 2018, it was confirmed that Middlesbrough acquired McNair as that side looks to make a return to the EPL. Perhaps McNair, who is still only 23 years old, can find new life for his career with a club that just missed out on promotion earlier this year.
9 Lucas Perez to Arsenal
If you’re anything like us, you actually didn't realize that Lucas Perez is still technically an Arsenal player. The forgotten front man who achieved next to nothing of note after making the transfer to the Gunners in August 2016 rejoined Deportivo on a loan deal nearly one year after putting pen to paper on his contract with Arsenal. Most recently, it has been reported that the man who was essentially replaced by Alexandre Lacazette and Pierre-Emerick Aubameyang still believes he can prove his worth to the EPL side. We’d be lying if we said we have tons of confidence in the veteran who turns 30 years old in September.
8 Vincent Janssen to Tottenham
Tottenham are lucky to have Harry Kane on the team, because Spurs have not been able to land a proper striker in transfer windows throughout the 2010s. Vincent Janssen is one of several players who were signed to score goals but who couldn’t achieve that mission while wearing Tottenham Lilywhite. Janssen made the move to White Hart Lane in August 2016, and Spurs sent him on loan to Fenerbahçe 12 months later. It has recently been reported that Janssen wants some clarity about his future ahead of the 2018-19 campaign. He probably shouldn’t hold his breath waiting to play Champions League fixtures for Spurs.
7 Adnan Januzaj to Sunderland
Adnan Januzaj scored a brilliant goal for Belgium at the 2018 World Cup, and nobody will be able to take that away from him. Unfortunately for Sunderland, nobody can take away that brief period of time he spent with the club after making a loan swap from Manchester United. Januzaj couldn’t find a long-term spot at either EPL side, and he signed a contract with Real Sociedad ahead of the 2017-18 season. It has been reported that United have a buy-back clause in the 23-year-old’s current deal, so it’s possible he could make a return to the EPL soon. Maybe he’ll prove doubters wrong if he’s given another chance.
6 Loris Karius to Liverpool
One cannot discuss goalkeeper Loris Karius joining Liverpool in May 2016 without mentioning his nightmare performance in the 2018 Champions League Final versus Real Madrid. Karius was directly responsible for two of the three goals surrendered on that fateful evening, and nobody could blame the EPL side if it were to move on from him ahead of the 2018-19 season. Of course, nobody can say what would have happened had Karius been at his best versus Real Madrid. Liverpool still could have lost. The way that match went leads one to believe Liverpool probably regret this transfer two years after the fact.
5 Alvaro Morata to Chelsea
Alvaro Morata was not a disaster during his first season at Stamford Bridge, but that doesn’t mean Chelsea got the player they thought they bought in July 2017. In fact, Morata’s form was so poor by the spring months that he was left out of the squad from Spain that traveled to Russia for the World Cup. Recently, it has been reported that Morata wants to make an exit from Stamford Bridge ahead of the upcoming season. That’s great and all, but the 25-year-old may not receive the offers he would have seen even a year ago. The wantaway striker may have to settle for not playing Champions League football over the next year of his career.
4 Davy Klaassen to Everton
Add Dutch attacker Davy Klaassen to the list of players who were more negatives than positives for an Everton side that splashed the cash in the summer of 2017. Klaassen seemingly disappeared from the squad well before the winter months, and he never made the transition to the new country and the EPL after completing the switch from Ajax. Everton, understandably, are already prepared to consider Klaassen a lost cause and move on from him so long as they can receive something worthwhile, such as money and a player, for his services. He has been linked with a move to Besiktas, where he may find himself a popular lad among the supporters.
3 Jack Wilshere to Bournemouth
Unlike with Joe Hart, Bournemouth absolutely should have known what they were getting when they let Arsenal off the hook by accepting Jack Wilshere on a loan in August 2016. Spoiler alert for those who don’t know: Wilshere’s stint at the club ended prematurely after he suffered an injury. That, sadly, has been the story of his once-promising career, and he and Arsenal parted ways this summer after the Gunners let his contract expire. While stranger things have happened, it does not appear as if he will ever again have a home with an EPL team. Maybe he should look at completing a transfer to Major League Soccer. Jogging around the United States during the summer months could be what he needs to stay healthy for an entire calendar year.
2 Fernando Llorente to Tottenham
One of these days, Tottenham are going to sign a striker who actually scores goals for the club. That day did not arrive after Fernando Llorente joined Spurs from Swansea City in August 2017. While he did notch a Champions League tally and also a hat-trick during an FA Cup match for the club, Llorente was not a good fit for a side used to having Harry Kane sit up top. It has been reported that Llorente desires to remain with Tottenham, perhaps with the hopes that he will again be asked to participate in a Champions League contest. Maybe he could do something Kane struggles with each season; hit the back of the net in August.
1 Wilfried Bony to Swansea City
Sometimes, there is truth behind the saying that teaches you can’t go home again. Striker Wilfried Bony scored goals and made a name for himself during his first stint with Swansea City, and the club brought him back from Manchester City in August 2017. The 29-year-old’s goal-scoring form was only a memory during the 2017-18 season, and he could not help Swans avoid relegation earlier this spring. There have been rumors that Swans could look to move on from him during the summer transfer window. What club would buy him following his lackluster season in which he only decreased the value Swansea would get for him is anybody’s guess.