Liverpool have missed out on potentially millions of pounds after losing Yasser Larouci on a free transfer to Troyes.
His contract expired this summer after telling the Reds that he had no intention of renewing his deal last year.
Anfield chiefs desperately tried to sell the defender but to no avail and the 20-year-old has now departed for nothing.
It has meant Liverpool have missed out on a huge payout due to compensation rules in England.
Among the clubs having a look, Leeds United and Brentford had been interested in the youngster and could have made offers last summer after ramping up their efforts.
However, a transfer failed to go through and Larouci remained at Anfield for another year despite his situation.
Liverpool desperately tried to convince the Frenchman to change his mind and had offered him a new contract.
But he rejected any offer outright, insisting that he wanted to leave to start playing immediately in the first-team.
Andy Robertson is firmly first-choice at the club, while James Milner has even been preferred to back-up option Kostas Tsimikas.
It meant that any avenue into the starting XI was always stacked against Larouci’s favour.
But his choice of club will surely leave a sour taste in Liverpool’s mouth with Manchester City the potential benefactors.
Troyes are one of several club’s under the City Football Group, along with the likes of New York City, Girona and Melbourne City, to name but a few.
Larouci has signed a five year contract with the Ligue 1 outfit, who also signed Metinho this summer from Fluminese for around €5m.
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It means both players could be at the Etihad one day should they develop how the club want them to.
Furthermore, if Larouci had signed for Brentford or Leeds this summer, Liverpool would have been entitled to a compensation fee.
FA rules state that clubs can expect a sum of money for any player under the age of 24 who leaves on a free transfer for another team in England.
If the two clubs cannot reach an agreement, the matter goes to a tribunal.
The Reds know the process well having done the same for Harvey Elliott, Danny Ings and Dominic Solanke in recent years.
However, with Troyes being in another country, those rules do not apply – instead, the FIFA regulations come into effect which means a much lower fee.
Instead, Liverpool can expect roughly £250,000 – a staggering amount lower than the millions they could have expected otherwise.
The Reds are looking to offload a number of fringe players this summer with Harry Wilson and Marko Grujic already departing.