Liverpool are considering selling Cody Gakpo to rivals Manchester City - a shock transfer that would be the first deal between the clubs since Raheem Sterling controversially quit Anfield for the Etihad in 2015.
Yet while Premier League title winner Gakpo would depart Anfield on considerably more cordial terms with the club's supporters should he leave, the choice to sell the Netherlands international - one of the Reds' few proven goalscorers - at this advanced stage of the transfer window is set to prompt more bewilderment than when Sterling travelled up the M62 over 11 years ago.
Sterling's bitter exit contrasts with Gakpo's standing
At that time, Liverpool looked miles behind City in the pursuit of English football's most coveted trophies and Sterling, who remained a teenager, had pushed for an exit for months, including declining to join the pre-season tour of the Far East that summer, after becoming disillusioned under then boss Brendan Rodgers.
Manchester City paid Liverpool £49m for Raheem Sterling in a controversial transfer between the two Premier League title rivals.
Ultimately, a deal valued at approximately £50m proved sensible for all parties involved, as the relationship between the England international and the Reds supporters concluded on bitter terms.
What remains unclear is why Liverpool are so prepared to negotiate with City, now a direct competitor, for one of their most talented attackers.
Gakpo is a well-liked character in the dressing room, especially amongst the club's Dutch contingent of Ryan Gravenberch, Jeremie Frimpong and club captain Virgil van Dijk, and his calm, understated demeanour has won him favour with numerous team-mates since he relocated to England nearly four years ago.
Reds' summer spending contradicts potential sale
The decision seems all the more baffling when you consider the Reds have spent the entire summer bolstering their options on the flanks, only to suddenly entertain the idea of leaving themselves short at the last minute by approving the sale of a player who has begun the season in fine form.
Cody Gakpo has a goal and an assist from the opening two games of the season.
Gakpo has long been on Tottenham's radar, but serious interest from City surfaced earlier this month and the former PSV Eindhoven star has now expressed his eagerness to make the move to the Etihad.
Consequently, Liverpool are now engaged in active discussions with City over a deal for a player who has consistently performed well at Anfield since his arrival in January 2023.
Like nearly all of his team-mates, the Dutchman experienced a slump in form under Arne Slot last season, but his excellent cross for Alexander Isak in Saturday's 2-2 draw with Nottingham Forest means he has now contributed 51 goals and 20 assists during his time on Merseyside.
Gakpo's contributions and a depleted title-winning squad
His standout season undoubtedly came two years ago when he netted 18 goals across all competitions as Slot's team clinched the Premier League title, but he could become the latest high-profile departure from a championship-winning squad that has been significantly depleted since the summer of 2025.
Since those glorious days following the confirmation of the club's 20th league title, Trent Alexander-Arnold, Jarell Quansah, Luis Diaz, Darwin Nunez, Caoimhin Kelleher, Andy Robertson, Mohamed Salah, Ibrahima Konate and Curtis Jones have all departed, and it seems Gakpo is now looking for a new challenge himself.
Coincidentally, Sunday marks exactly one year since Gakpo inked a new contract with Liverpool. At that time, he spoke of creating "more beautiful moments" in his journey with the club and was vocal about how content he and his young family were in the North West.
In reality, there haven't been many more of those moments he referred to, especially during a disappointing year for the club overall throughout the 2025/26 season, but the new contract has at least maintained his value at a time when the transfer market has become perplexing to many regular football fans.
Potential fee and replacement targets
Rumours of an £85m deal with City might seem steep at first glance, but that was the sum the Etihad club received from Tottenham for winger Savio, who had nowhere near the track record of Gakpo in either the Premier League or Champions League.
That seems like a reasonable starting point for negotiations, but the Reds are unlikely to approve any exit until they have secured another winger to their squad before Tuesday's 11pm deadline.
Yankuba Minteh, who has seen two bids from Brighton and Hove Albion turned down, remains in the frame and a deal for the Gambia international could be revived if the Seagulls reduce their £80m valuation.
Inquiries have been made about Ismaila Sarr at Crystal Palace and there were preliminary discussions with Paris Saint-Germain earlier in the window regarding Ibrahim Mbaye, who is now on the verge of signing for Aston Villa.
Said El Mala, of FC Koln, has been shortlisted and Liverpool enquired about Brazil international Endrick but were told Real Madrid intend to retain him.
Belgium international Matias Pardo-Fernandez is still at Lille, despite interest from Aston Villa and Newcastle, and the Reds' recruitment team have been described to the ECHO as 'juggling balls' at this stage of the window.
The summer-long focus on bolstering wide areas directly contradicts the notion of offloading Gakpo without securing a replacement of similar calibre, even with the impending arrival of Bradley Barcola, who is scheduled for a medical on Sunday.
France international Barcola will switch from PSG for a fee of £123m but the Reds are still in the market for another forward before 11pm on Tuesday.
Van Dijk's stance on Gakpo's future
Liverpool's capacity to secure such a deal will greatly influence what comes next in the career of Gakpo.
Club captain Virgil van Dijk, for one, has made his position clear about his team-mate for club and country and what he thinks of Liverpool's controversial decision to potentially weaken their squad and strengthen a direct rival.
After Saturday's disappointing 2-2 draw with Forest, in which the versatile Gakpo was deployed on the right wing, Van Dijk said: "He's a quality player and I think we should keep quality players, but let's see what the next three days bring.
"It's pretty clear I want him to stay, not only because he is the quality player that he is, but also he's a friend of mine and I think he will be very important for us."
