Manchester city transfer news: The top 10 worst signings of Pep Guardiola KIK BALL

English midfielder Jack Grealish is leaving the Etihad Stadium on loan to Everton. Once the most expensive English player in history, this move has not worked out well for Pep Guardiola. On this occasion, we take a look at his 10 worst signings during his managerial career – and they include some big names.

Grealish and Guardiola often seemed an unusual pairing – a uniquely talented player and a coach who demands strict structure and rehearsed tactical patterns. Four years after Grealish’s record-breaking transfer from Aston Villa to Manchester City, the most expensive in Premier League history, their partnership is sadly coming to an end.

Grealish is now set to join Everton on loan after agreeing his departure from City earlier this summer. It became clear his time at City was ending back in January, when he was left out of the squad for the 2025 Club World Cup. After two disappointing seasons, Guardiola tried to help Grealish return to his best but admitted he had lost hope in January: “Do I want the Jack who won the treble back? Yes, I do. But I’m trying to be honest with myself.”

Meanwhile, City have brought in Jeremy Doku (2023), Savinho (2024) and Ryan Cherki (summer 2025), who are seen as replacements for Grealish. His £100 million career at the Etihad Stadium underlines Guardiola’s occasional transfer misses.

Where does Grealish rank among Guardiola’s worst signings? Here is the top 10:

10. Nolito (Man City, £14 million)

Guardiola knew Nolito from his time with Barcelona’s reserves. He brought him to City from Celta Vigo in his first summer with the Citizens. Nolito blossomed late in La Liga, but the step up to England was too big. He scored twice in his second Premier League game but struggled afterwards. He also complained about Manchester’s weather affecting his daughter’s skin colour, which attracted media attention. Nolito played only one season at City, making 9 league starts and scoring 4 goals, before moving to Sevilla.

9. Martin Caceres (Barcelona, £14 million)

Guardiola’s first signing as Barcelona coach, but one of his worst. Caceres arrived from Villarreal but was only the fourth-choice centre-back. He played just 8 La Liga games, winning only 4, a poor return in a year Barca won the league. He didn’t feature in the Champions League final, with Guardiola preferring Yaya Toure as a makeshift defender. Cáceres left for Juventus after one season.

A promising centre-back with goal-scoring ability at Roma, but he failed to settle in Munich. Over two seasons, he made just 24 Bundesliga appearances and made several costly errors, including a red card against City in the Champions League and mistakes in knockout games against Barcelona. He moved to Juventus after his second season.

7. João Cancelo (Man City, £60 million)

Talented but with a difficult personality, which strained his relationship with Guardiola. Cancelo had two strong seasons, helping City win titles in 2020-21 and 2021-22, but ongoing conflicts and disrespect, like wearing headphones during team meetings, led to his departure. He went on loan to Bayern and Barcelona before City sold him to Saudi Arabia in 2024.

6. Claudio Bravo (Man City, £17 million)

Guardiola showed his uncompromising approach by dropping Joe Hart for lack of ball skills and signing Bravo. Despite success at Barcelona, Bravo struggled in the Premier League, making mistakes in matches against United and Barcelona in the Champions League. He was replaced after five months but stayed at City until 2020, winning some trophies.

5. Dmytro Chygrynskiy (Barcelona, £22 million)

The Ukrainian defender was signed to strengthen Barca’s defence after their treble but did not fit the team’s style. He played just 851 minutes and was often booed by fans. He returned to Shakhtar Donetsk at a significant loss after one season.

4. Jack Grealish (Man City, £100 million)

The most expensive Guardiola signing, but only one genuinely good season out of four. Grealish played a specific role in the treble-winning team, but his lifestyle after success, including heavy drinking during celebrations, did not sit well with the coach. He played very little in the last two seasons, leaving with 17 goals and 23 assists in 157 games.

Arriving after success with Leeds and England, Phillips started poorly – shoulder injury, surgery, and doubts over his lifestyle after the 2022 World Cup. He made only six starts for City before going out on loan.

Signed as a record-breaking left-back, Mendy immediately suffered a knee injury and was out for a long period. Upon return, he was no longer the same player, lost the manager’s trust, and was criticised for poor discipline (including being late to training). Suspended in 2021 over serious allegations and later cleared, he left City in 2023.

1. Zlatan Ibrahimović (Barcelona, £59 million)

Talented but clashed with Guardiola’s ego. The biggest issue arose when Messi wanted to play as a centre-forward, leaving Zlatan sidelined. After Barca’s Champions League exit to Inter Milan, Ibrahimović shouted at Guardiola, “You can go f*** yourself!” He went on loan to AC Milan before being sold at a significant loss.

This article was originally published on Fotbal Portal.

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