Five transfer windows that were worse than Liverpool 2025 after Jamie Carragher comments

It was a comment from Jamie Carragher that continues to spark debate.

"If this doesn't change in the next two or three months under [Andoni] Iraola, and these players improving, I think we're going to be looking at that as arguably the worst transfer window we've probably seen in Premier League history, when you consider the fees for these players, and what it's going to do for Liverpool," he said on Monday Night Football.

Carragher, of course, was referring to Liverpool's 2025 summer transfer window, when they spent a record £446 million on a host of new signings. In fact, they broke the British transfer record twice.

Florian Wirtz arrived from Bayer Leverkusen for £116 million before Alexander Isak was snapped up for £125 million on deadline day. Hugo Ekitike, Milos Kerkez, Jeremie Frimpong, Giovanni Leoni and Armin Pecsi were also brought in to elevate their title prospects.

Ekitike was arguably Liverpool's standout performer last season under Arne Slot, scoring 17 goals in all competitions before suffering an ACL injury in April. However, the rest of those arrivals failed to live up to expectations in what was a dismal campaign across 2025-26.

Speaking on Monday, Carragher gave his take on Liverpool's transfer business in 2025.

"It's the first game of the season, but my fear is this window of 12 months ago could set Liverpool back a year or two, to fix it," he said. "Yes, it's one game under Iraola, but we're talking 12 months of underperformance from all of these players except [Ekitike]."

Carragher added: "The idea of these players wasn't just coming in and being good players. It was to create almost a little dynasty for Liverpool.

"Let's not forget, Liverpool won the league two years ago. These [players] were supposed to do what City have done over the last few years, or United in the past, where they go and win two or three leagues in five years."

As a result of his comments on MNF, a debate around the worst transfer window in Premier League history began to swirl online, with fans discussing what they believed to be the most disastrous.

So, we thought we'd chip in with some of our contenders, featuring Manchester United's infamous summer of 2023 and Queen Park Rangers' abysmal attempt at a rebuild ahead of the 2012-13 campaign.

Chelsea – summer 2017

After winning the 2016/17 Premier League title by seven points, Chelsea were keen to back Antonio Conte with some high-profile signings.

Alvaro Morata replaced Diego Costa in a club-record £60 million deal, while Tiemoue Bakayoko and Danny Drinkwater were brought in for big money alongside Antonio Rudiger and Davide Zappacosta.

In the coming months, Morata showed glimpses of brilliance but struggled for consistency. Bakayoko, Drinkwater and Zappacosta also found it difficult at Stamford Bridge, with Rudiger being the only positive in an otherwise abysmal window.

Alvaro Morata — Real Madrid: £60m

Tiemoue Bakayoko — Monaco: £40m

Danny Drinkwater — Leicester City: £35m

Antonio Rudiger — Roma: £29m

Davide Zappacosta — Torino: £23m

Willy Caballero — Manchester City: free

Man Utd – summer 2023

Where do we start? Erik ten Hag was backed with a hefty budget in the summer of 2023, a year after they spent big on Antony (£81.3m), Casemiro (£70m) and Lisandro Martinez (£56.7m).

To kick things off, Rasmus Hojlund netted 15 goals in his first season at United, with nine of these coming in the league, but the Dane struggled for consistency and was sold to Napoli for £38 million this summer.

Andre Onana, a £47.2 million signing from Inter Milan, gave us a portfolio of clangers in his debut season after being brought in to replace David de Gea. Mason Mount, meanwhile, is the only player from the group to still play for United, although his time at Old Trafford has been plagued by injuries.

It was an eventful deadline day, too, with Sofyan Amrabat and Sergio Reguilon arriving on loan alongside Jonny Evans and Altay Bayındir in what felt like a desperate move.

Rasmus Hojlund — Atalanta: £64m + £8m add-ons

Mason Mount — Chelsea: £55m + £5m add-ons

Andre Onana — Inter Milan: £43.8m + £3.4m add-ons

Altay Bayındır — Fenerbahce: £4.3m

Sofyan Amrabat — Fiorentina: loan

Sergio Reguilón — Tottenham: loan

Jonny Evans — free transfer

Liverpool – summer 2010

Despite Carragher's comments, I'd argue Liverpool's summer window in 2010 is the club's worst to date.

After the departure of Javier Mascherano to Barcelona, Raul Meireles was signed from Porto for around £11.5 million but he struggled to hit the ground running under Roy Hodgson and was sold to Chelsea a year later.

The arrivals of Christian Poulsen, Paul Konchesky, Brad Jones and Danny Wilson failed to inspire, and neither did Joe Cole, Milan Jovanovic and Fabio Aurelio, despite the trio joining on free transfers.

Raul Meireles — Porto: £11.5m

Christian Poulsen — Juventus: £4.5m

Paul Konchesky — Fulham: £3.5m

Brad Jones — Middlesbrough: £2.3m

Danny Wilson — Rangers: £2m

Jonjo Shelvey — Charlton: £1.7m

Joe Cole — Chelsea: free

Milan Jovanović — Standard Liege: free

Fabio Aurelio — free/re-signed

QPR – summer 2012

After narrowly avoiding relegation in 2011-12, QPR tried to rebuild their squad with a host of high-profile names. The problem? Most were approaching the latter stages of their careers.

A 31-year-old Park Ji-Sung arrived from Manchester United alongside a host of experienced names, including Jose Boswingwa, Robert Green, Andy Johnson and Ryan Nelson.

Esteban Granero was their most expensive arrival from Real Madrid, but after scoring one goal in 28 appearances, he joined Real Sociedad in 2014.

Esteban Granero — Real Madrid: £9m

Stephane Mbia — Marseille: £5m

Park Ji-Sung — Manchester United: £2.5m

Samba Diakite — Nancy: £3.5m

Junior Hoilett — Blackburn Rovers: compensation fee

Julio Cesar — Inter Milan: free

Jose Bosingwa — Chelsea: free

Robert Green — West Ham: free

Andy Johnson — Fulham: free

Ryan Nelsen — free

Fabio da Silva — Manchester United: loan

Sam Magri — Portsmouth: free

Tottenham – summer 2013

At the time, Garth Crooks memorably declared that Tottenham had "sold Elvis and signed the Beatles" when they brought in the so-called 'Magnificent Seven' following Gareth Bale's departure.

Vlad Chiriches was the first player to walk through the doors when he joined from Romanian side Steaua Bucharest for around £8.5 million. He ended up making 43 appearances in two seasons before being sold to Napoli in 2015.

Chiriches's arrival was followed by Christian Eriksen, who was by far their best signing that summer. The Dane notched 51 goals and 59 assists in 226 Premier League appearances during his seven-year stint at Spurs.

Erik Lamela is also widely regarded as one of the best signings of 2013 and made over 250 appearances across eight seasons, recording 37 goals and 44 assists.

Etienne Capoue, Nacer Chadli, Paulinho and Roberto Soldado, however, ended up being huge disappointments.

Erik Lamela — Roma: £26m

Roberto Soldado — Valencia: £26m

Paulinho — Corinthians: £17m

Christian Eriksen — Ajax: £11.5m

Etienne Capoue — Toulouse: £9m

Vlad Chiriches — Steaua Bucharest: £8.5m

Nacer Chadli — FC Twente: £7m

READ MORE: What happened to the seven players Spurs signed with the Gareth Bale money

Honourable mention: Huddersfield summer 2018

Much like the aforementioned QPR, Huddersfield needed a productive summer after narrowly avoiding the drop in 2017-18. Unfortunately, the impact of that window is still visible today.

The Terriers spent a hefty amount ahead of their second season in the Premier League. Terence Kongolo, who joined on a permanent deal from Monaco for a club-record £17.5 million, struggled to meet expectations.

Having scored just 28 league goals across 2017-18, the club needed attacking reinforcements, yet the additions of Adama Diakhaby and Ramadan Sobhi added very little going in that aspect.

It was a window to forget, and that soon became apparent in the months that followed. They finished bottom of the Premier League with three wins from a possible 38.

Terence Kongolo — Monaco: £17.5m

Adama Diakhaby — Monaco: £8m

Ramadan Sobhi — Stoke City: £5.7m

Florent Hadergjonaj — Ingolstadt: £4.5m

Juninho Bacuna — Groningen: £2.6m

Erik Durm — Borussia Dortmund: £2.6m

Jonas Lossl — Mainz: undisclosed fee

Ben Hamer — Leicester City: free

Isaac Mbenza — Montpellier: season-long loan