The Ten Worst Signings in Premier League History: A Ranked Analysis of Players and Managers

Jack Grealish and Pep Guardiola often felt like an odd couple, a strange alliance between the ultimate individual and a coach who insists on structure and rehearsed patterns of play. Now, four years after their unlikely relationship began with the player’s Premier League record transfer from أستون فيلا to Manchester City, it has come to a sad end.

Grealish is set to join Everton on loan after effectively agreeing to leave City at the start of the summer when he was left out of the squad for the Club World Cup. The departure follows two bitterly disappointing seasons for the England international after the high of winning the treble in 2023. Guardiola desperately wanted to help Grealish return to those heady days, but back in January he effectively admitted he had given up on that aim, remarking: "Do I want the Jack that won the treble? Yeah, I want it, but I try to be honest with myself."

City have already moved on from Grealish, signing Jeremy Doku in 2023, Savinho in 2024 and Rayan Cherki this summer to compete with him, and the £100-million man’s disappointing career at the Etihad Stadium underlines that Guardiola does not always get it right in the transfer market.

So where does Grealish rank among the worst signings Guardiola has ever made? BALLGM runs down the top 10:

Jack Grealish and Pep Guardiola often felt like an odd couple, a strange alliance between the ultimate individual and a coach who insists on structure and rehearsed patterns of play. Now, four years after their unlikely relationship began with the player’s Premier League record transfer from Aston Villa to Manchester City, it has come to a sad end.

Grealish is set to join Everton on loan after effectively agreeing to leave City at the start of the summer when he was left out of the squad for the Club World Cup. The departure follows two bitterly disappointing seasons for the England international after the high of winning the treble in 2023. Guardiola desperately wanted to help Grealish return to those heady days, but back in January he effectively admitted he had given upon that aim, remarking: “Do I want the Jack that won the treble? Yeah, I want it, but I try to be honest with myself.”

So where does Grealish rank among the worst signings Guardiola has ever made? بالجم runs down the top 10:

Guardiola had known Nolito since the forward’s days in Barcelona‘s reserve team and had watched his progress closely before bringing him to City from Celta Vigo during his first summer in charge of the Blues.

Nolito was a late bloomer, having only started to thrive in La Liga in his late 20s, and the move to City was simply to big of a step up for him. He scored twice against Stoke City in his second appearance, but could not build on his strong start and struggled to adapt to life in England, eventually making headlines by declaring that the lack of sunshine in Manchester had made his daughter’s skin change colour and that she looked like she had been “living in a cave” as a doctor even advised him to give her vitamin D tablets.

Nolito lasted just one season at City, making only nine Premier League starts while scoring four times, before returning to his natural habitat by joining Sevilla.

Martin Caceres was the first signing Guardiola ever made as a coach, but proved to be one of his worst. The centre-back joined Barca from فياريال having spent the previous season on loan at Recreativo de Huelva, and despite arriving for what was a sizeable transfer fee at the time, Caceres barely got a look in as he quickly dropped down the pecking order to become fourth-choice centre-back.

He made just eight La Liga starts all season and Barca won just four of them, a miserable ratio considering they stormed to the title that season. His standing was so low that even when Dani Alves and Rafael Marquez were injured for the Champions League final, he still didn’t get in the team, with Guardiola opting to play Yaya Toure at centre-back instead.

Caceres left for يوفنتوس that summer, lasting just one season at Camp Nou.

Medhi Benatia had impressed as a goal-scoring centre-back for Roma, but suffered an acrimonious departure from Stadio Olimpico as he joined Bayern in the summer of 2015, ahead of Guardiola’s second campaign in Munich. The coach, however, quickly lost trust in him, and over two seasons handed Benatia just 24 الدوري الألماني starts.

ال Morocco international also became notorious for producing high-profile errors, such as getting sent off against City in a Champions League group-stage game and making costly lapses in both legs of the semi-final tie against Barcelona, which Bayern lost 5-3 on aggregate.

He subsequently had a reduced role in his second season, Guardiola’s last, and then left for Juventus.

Joao Cancelo can be filed alongside Zlatan Ibrahimovic in the category of being a brilliant player but with a volcanic personality which ultimately ruined his relationship with Guardiola. The Portugal international had two fantastic seasons with City, but clashed too many times with the coach, and there was only ever going to be one winner.

It has been revealed that Cancelo got off to a rocky start just weeks after completing his £60m ($76m) move from Juventus and threatened to leave after losing his place in the line-up to Kyle Walker. Urged to change his ways by sporting director Txiki Begiristain, Cancelo reinvented himself as an inverted left-back and was instrumental to City’s successive title wins in 2020-21 and 2021-22.

But he could not handle being dropped again after the 2022 World Cup and started disrespecting Guardiola, even wearing headphones during one of his team talks. The coach made it clear that Cancelo had to leave “for the good of the team” and was loaned out to Bayern Munich, where he also endured a disappointing spell.

He continued to underwhelm during a subsequent loan at Barcelona before he was eventually sold to Saudi side Al-Hilal in 2024.

Guardiola showed his ruthless nature when he first took over at City in the summer of 2016 by immediately deciding that Joe Hart, the hero of the 2012 and 2014 league titles, was not the goalkeeper for him due to his lack of ball-playing ability. However, he made a rod for his own back by choosing Claudio Bravo to replace Hart.

Bravo had won two league titles with Barcelona, but was not as good with his feet as team-mate Marc-Andre ter Stegen (whom Guardiola also considered) and really struggled to adapt to the Premier League. He made a howler on his debut against مانشستر يونايتد and was sent off in a 4-0 drubbing at Barca in the Champions League.

Bravo lasted barely five months as City’s No.1 before Guardiola dropped him for Willy Caballero and then signed a replacement in Ederson. Despite his embarrassing fall from grace, Bravo remained at City until 2020, making 61 appearances and significantly improving his medal collection, and he looks back on his time at the Etihad very fondly.

“I had a marvellous time at Manchester City,” the Chilean told The Players’ Tribune. ”I’m telling you, it was successful in every sense. All four of my seasons there were amazing. I guess people remember different things. When I look back at that time, I recall that I played in two League Cup finals and two Community Shields – and won them all.”

Barcelona made a number of signings in Guardiola’s second summer in charge to build on their treble success, and towering centre-back Dmytro Chyhrynski arrived from Shakhtar Donetsk to bolster their defence. It soon became apparent, however, that the Ukrainian did not fit with Barca’s style of play.

He was not exactly a disaster, as Barca won eight out of the 10 La Liga matches he started while remaining unbeaten, but he could not match the standards of his team-mates and was on occasion booed by the Camp Nou faithful. He played just 851 minutes for Barca before heading straight back to Shakhtar after one season at a loss of €10m (£8.7m/$10m).

“I never say that I played for Barca. I say: ‘I was at Barca’. And that’s different, because to say that you played there you need to have been an important part of the team,” he admitted to Relevo years after his departure from Catalunya. “I had mistakes that at Barca are not acceptable, because the bar is very high.”

Grealish remains Guardiola’s most expensive signing ever, and the harsh truth is that he had just one good season out of four under the Catalan.

It was, admittedly, a very good one in terms of achievements as Grealish mastered the very specific role Guardiola had carved out for him in his treble-winning side: to keep hold of the ball, stick to the touchline and allow the other players to reset. Described as ‘the rest station’ by the coaching staff, it was not exactly a flattering role for a player who was previously regarded as the ultimate street footballer while at Aston Villa, but it was a vital one, and Guardiola stressed ahead of Grealish’s departure in 2025 that “winning the treble would not have been possible without Jack”.

But how Grealish reacted to winning the treble proved to be his downfall. He got so drunk after winning the Champions League that he had to be held up by Kyle Walker following the team’s celebrations in Ibiza, and his antics during the trophy parade went viral. The party barely stopped that summer, and while Guardiola is partial to his players letting their hair down on occasion, the image of Grealish’s never-ending bender cannot have sat well with him.

The midfielder made just 10 league starts the following season and went the entirety of 2024 without scoring a goal for his club. The following season went even worse as Grealish started just 11 matches across the Premier League and Champions League and was an unused substitute for the FA Cup final.

He leaves City having provided just 17 goals and 23 assists in 157 matches, and contributed to 10 more Premier League goals during his time at Villa than with Guardiola’s side. And so while City fans will continue to love Grealish for his laddish ways, it is difficult to argue that from a financial point of view he has been one of the coach’s worst-ever buys.

Kalvin Phillips’ transfer to City in the summer of 2022 made sense at the time, as the midfielder had honed his playing style at Leeds United under Marcelo Bielsa, one of Guardiola’s coaching mentors, and played a key role in England’s run to the final of the European بطولة a year earlier.

But Phillips got off to a difficult start at the Etihad as he injured his shoulder in a friendly against Barcelona and needed to have surgery. Guardiola then questioned Phillips’ lifestyle by accusing him of returning from the 2022 World Cup overweight and kept leaving him out of the starting line up, including when he rotated the rest of his squad for the FA Cup semi-final against شيفيلد يونايتد.

Not even a three-match suspension for Rodri in the first half of the following campaign could help Phillips stake a claim for a regular role, and he left City for loan spells at West Ham and Ipswich Town having made just six starts in all competitions, three of which City went on to lose.

After a trophy-less first season with City, Guardiola went on an almighty spending spree that saw him splash out on £250m ($318m)-worth of new players. To the surprise of many, he prioritised signing full-backs, bringing in Walker and Danilo before paying £52m ($65m) to sign Benjamin Mendy from Monaco, a then world-record fee for a defender.

Mendy had been one of the leading lights of Monaco’s charge to the Ligue 1 title and the Champions League semi-finals – knocking City out on the way – and his signing seemed perfectly logical. However, disaster struck when he tore his anterior cruciate knee ligament within his first few weeks at the club, keeping him out for seven months.

He didn’t impress Guardiola much after returning though, and his professionalism was questioned after he turned up three hours late for training after attending an Anthony Joshua fight. Mendy then had to undergo more surgery on his knee in November 2018, and once he returned to full fitness he remained on the fringes of the team, never starting more than half of City’s Premier League games in a season.

He was suspended by the club in September 2021 after being charged with multiple counts of rape, though he was later found not guilty on all counts and successfully sued City for unpaid wages while he was suspended. Mendy left City when he his contract expired in 2023 to join Lorient, before later moving to FC Zurich in 2025. He is currently a free agent after leaving the Swiss side last May.

Ibrahimovic was one of the few players who had the confidence and star-quality to fit into Guardiola’s all-conquering Barcelona side, and at first he shone, scoring 10 goals in his first four months in Catalunya, including a winner against Real Madrid.

But it was only a matter of time before his infamously massive ego clashed with Guardiola, whom he later referred to as “that idiot of a manager” in his eye-opening autobiography I Am Zlatan.

The first flashpoint came when Messi demanded to play through the middle and not on the right wing, leaving Ibrahimovic on the fringes of the game. He recalled: “The balls passed through Messi, and I didn’t get to play my game. On the pitch, I’ve got to be as free as a bird. I’m the guy who wants to make a difference at every level. Guardiola sacrificed me. That’s the truth.”

Ibrahimovic’s relationship with Guardiola reached boiling point after the Champions League semi-final elimination to Inter, the Swede’s former club, when the striker yelled “You can go to Hell!” at the coach. There was no going back after that, and Ibrahimovic joined AC Milan on loan that summer, later sealing a permanent move for £20m ($25m), a loss of almost £40m ($50m). To make matters worse, Samuel Eto’o, who was included in the initial transfer deal the year before, had won the treble with Inter.