Liverpool failed to land Anthony Gordon in a move which would have equalled their transfer record, but they are no strangers to such market disappointment.
Anthony Gordon
While not an outright club-record transfer in itself, the convoluted deal arranged with Newcastle which involved Gordon swapping places with Joe Gomez and a sack stuffed full of £30m represented a theoretical matching of Liverpool’s 2018 outlay on Virgil van Dijk.
That will remain the high transfer window mark in Liverpool’s history for as long as Darwin Nunez toils trying to bring his initial £64m fee up to the maximum of £85m with clauses.
The Reds have retained their interest in the England forward but any resumption of talks would require a fee at least as substantial, if not more so now Newcastle have eased their PSR concerns and Liverpool’s desire is public.
Things went as far as a planned medical for both Gordon and Gomez but Brighton and Nottingham Forest ruined all the fun by massively overpaying for other Newcastle players.
Moises Caicedo
It is not often two supposedly elite clubs so hilariously reduce themselves to barely functional shambles in pursuit of the same player, yet Chelsea and Liverpool engaged in a battle of one-upmanship so incompetent in summer 2023 that even Brighton, the chief beneficiaries of their nonsense, were left bewildered when it was over.
Chelsea bargained and bartered over Caicedo for weeks, as if they had never before dealt with Brighton and were not familiar with their obstinance. The Blues then pretended to consider drawing up a list of alternatives despite it being patently obvious they would simply end up paying precisely what was necessary for their known top target. Then Liverpool barged in with a £111m offer which raised those stakes, Caicedo rejected them and Chelsea suddenly found a spare £115m lying around in one of Todd Boehly’s coat pockets.
Liverpool made their move because, in the words of Jurgen Klopp, “we were interested in Bellingham and realised it would not happen,” then “the whole market for No 6s went up”. Their offer was obviously accepted by a stunned Brighton but Caicedo was set on joining Chelsea, whose naivety cost them a fair whack more in add-ons and ‘a significant sell-on clause’.
All parties are probably happy enough with their lot a year later, but the amount of copium Liverpool needed at the time was generationally funny.
Naby Keita
If Keita’s performances for Liverpool had managed to match even a fraction of the vigour, tenacity and consistency with which they tracked him then his statue would already have been constructed outside Anfield.
The Reds were singularly determined to land their man by any means necessary, but Leipzig were not for budging in summer 2017. “There were two offers from Liverpool and in between times also a telephone call between the clubs,” manager Ralf Rangnick said at the time, with those bids coming in at £57m and then £66m – both eclipsing the £36.9m paid for Mo Salah in the same window.
The Bundesliga side eventually relented a couple of weeks later, but with a catch. Liverpool agreed to pay the £48m release clause which became active in the midfielder’s contract the following summer, plus a premium based on Leipzig’s finish in the upcoming season, to claim dibs 12 months in advance.
When that deal was organised it was the most expensive in Liverpool history, still passing that Salah bar. By the time Keita actually joined a year later, Van Dijk had transformed the scene.
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Thomas Lemar
Yet Liverpool were not done. Their Keita breakthrough was cause for celebration but still left a perceived hole in their engine room, one they felt Lemar of Monaco could fill.
Their push for the Frenchman went all the way to deadline day, with already difficult circumstances compounded by Lemar being away on international duty at the time.
Not to be deterred, Liverpool proceeded with offers worth £55m and £64m but Monaco, who had already shed many of the key assets in a squad which reached the Champions League semi-finals, stood firm.
The Reds had put a medical team on standby in Paris just in case, only for the move to entirely collapse when Arsenal barged in looking laughably amateurish, perhaps powered by spite after Liverpool had signed Alex Oxlade-Chamberlain from them.
Virgil van Dijk
The Gordon move would have equalled Liverpool’s club-record transfer, with the Reds understandably reluctant to dislodge Van Dijk from that particular £75m throne.
That sort of outlay should guarantee success and Liverpool were always so convinced Van Dijk represented such a sure thing, to the extent they went above and beyond to seduce the player before even trying to flatter the club in question.
Southampton were justifiably infuriated by that and Liverpool were forced into not only an apology but an embarrassing scaling back of their interest. It was a situation unbefitting of the reputation Michael Edwards and his transfer team would soon come to earn, as the Reds crumbled under the threat of a Premier League investigation into their illegal approach of a player whose club had not authorised such close contact from a potential suitor.
Van Dijk was sufficiently unsettled as to be unavailable for the Southampton pre-season tour squad, hand in a transfer request and miss all but three minutes of the first six games of the campaign with a serendipitous ankle injury, before finally resuming regular first-team duties in late September.
Liverpool waited until just after Boxing Day for the dust to settle, ensuring to follow the established protocol when actually bothering to contact Southampton to sort out a fee before the formalities of personal terms were finalised. They ended up paying £25m on top of the £50m that had been mooted the prior summer and will still feel as though it was a bargain.
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