Five transfer windows that were tougher than Liverpool 2025, according to Jamie Carragher
Jamie Carragher’s comment has kept fans talking. On Monday Night Football, he said, “If things don’t get better in the next two or three months under [Andoni] Iraola, and these players don’t improve, this might be one of the worst transfer windows in Premier League history. Considering the money spent and what it means for Liverpool, it’s worrying.”
He was talking about Liverpool’s 2025 summer transfer window, where they spent a record £446 million on new players, breaking the British transfer record twice. Florian Wirtz joined from Bayer Leverkusen for £116 million, and Alexander Isak was signed for £125 million on deadline day. Other signings included Hugo Ekitike, Milos Kerkez, Jeremie Frimpong, Giovanni Leoni, and Armin Pecsi, all brought in to boost Liverpool’s title chances.
Ekitike was probably the best new player last season, scoring 17 goals before an ACL injury in April. Unfortunately, the others didn’t meet expectations, and the season was tough for Liverpool.
Carragher mentioned his worries that this transfer window might set Liverpool back a year or two. “It’s just the first game under Iraola, but these players, except for Ekitike, have underperformed for 12 months,” he said. The hope was that these signings would help Liverpool build a strong team for the future, like Man City or United have done by winning several league titles in a few years.
After Carragher’s words, fans started debating online about the worst Premier League transfer windows ever. So, we decided to join the conversation with some examples, including Manchester United’s summer of 2023 and Queens Park Rangers’ rebuild before the 2012–13 season.
Chelsea’s 2017 window was a mixed bag. After winning the league, they spent big to support Antonio Conte. Alvaro Morata was bought for a club-record £60 million to replace Diego Costa. Tiemoue Bakayoko, Danny Drinkwater, Antonio Rudiger, and Davide Zappacosta also arrived. Morata showed some good moments but wasn’t consistent. Bakayoko, Drinkwater, and Zappacosta struggled, while Rudiger was the only real success.
Manchester United’s 2023 summer brought high hopes but mixed results. They spent a lot after already making big signings the previous year. Rasmus Hojlund scored 15 goals but was sold after struggling for consistency. Andre Onana, signed to replace David de Gea, had some tough moments. Mason Mount is the only player still at the club but has battled injuries. They also made several loan signings in what seemed a desperate deadline day.
Looking back, some say Liverpool’s 2010 summer window was their worst. After Javier Mascherano left, Raul Meireles joined but didn’t perform well and left for Chelsea a year later. Other signings like Christian Poulsen, Paul Konchesky, and Brad Jones didn’t impress, and free transfers including Joe Cole failed to make an impact.
After barely escaping relegation in 2011-12, QPR tried to rebuild with many experienced players, but most were past their peak. Signings like Park Ji-Sung, Jose Bosingwa, and Robert Green couldn’t save the team. Esteban Granero was their most expensive signing but didn’t deliver much.
Back in 2013, when Tottenham spent Gareth Bale’s money, some thought they’d struck gold. But while Christian Eriksen and Erik Lamela were good signings, others like Etienne Capoue, Nacer Chadli, Paulinho, and Roberto Soldado were disappointments.
Huddersfield’s 2018 summer spending after surviving relegation didn’t go well either. Big-money signing Terence Kongolo struggled, and other attacking players brought in added little. The season ended with Huddersfield at the bottom with just three wins.
Each of these examples shows how hard it is to get transfers right and how a bad window can impact a club for years.