As the England midfielder leaves the Etihad Stadium for Everton, GOAL counts down the worst deals of the Manchester City coach's career
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 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? GOAL runs down the top 10:
Getty Images10Nolito (Man City, £14m)
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.
AdvertisementGetty Images9Martin Caceres (Barcelona, £14m)
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 Villarreal 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 Juventus that summer, lasting just one season at Camp Nou.
Getty8Medhi Benatia (Bayern Munich, £22m)
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 Bundesliga starts.
The 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.
Getty7Joao Cancelo (Man City, £60m)
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.
