Tottenham have always been reluctant to spend their way out of a crisis. There is a logic to that if you believe their problems are temporary and ill-fated rather than foreseeable and self-inflicted.
The stars have not conspired to align in the wrong order over north London, but it is impossible to escape the suspicion that Spurs would not be where they are had Cristian Romero, Micky van de Ven and Ben Davies remained fit.
The absences of Guglielmo Vicario, Richarlison, Wilson Odobert, and Destiny Udogie – on top of Rodrigo Bentancur’s suspension – have compounded an injury crisis the likes of which Ange Postecoglou says he has never experienced.
So to January, and to the crux of the dilemma on which his project will stand or fall. Do Tottenham buy oven-ready, or repeat their summer pattern, when apart from Dominic Solanke, the average age of their arrivals was 18 years and three months?
Both have been toyed with over the years, and both have had varying success. Unlike so many around them Tottenham have not flirted with the boundaries of the Premier League’s Profitability and Sustainability Rules (PSR).
But since the sliding doors moment of the 2019 Champions League final they have meandered between two possibilities – the necessary immediate fixes, which have usually fixed little, and the hopeful potential of young players who might one day be sold on for a profit.
Once upon a time the big misses – DeAndre Yedlin, Clinton N’Jie, Georges-Kevin N’koudou – were papered over by the hits: Dele Alli, Mousa Dembele, Toby Alderweireld.
Now with the successes drying up, Postecoglou is left with overburdened senior players, those on the fringe ill-suited to his system, and little optimism that much will change in January.
Looking back at these 18 deals that went wrong explains their dilemma in the new year:
Jack Clarke
In his defence, Clarke rocked up to a club that had just gone 18 months without making a signing. By any measure, that is not a good state of health. It might have been expected, in that light, that the then teenager would at least have been given opportunities.
Instead, he never made a competitive appearance in the Premier League, despite looking like a serious talent when he eventually wound up at Sunderland on his fourth loan spell, from where he earned a return to the top flight with Ipswich.
Tanguy Ndombele
Had that been the status quo, fine. The same day a £62m deal – then a club record – was agreed for Tanguy Ndombele.
It was one of the great puzzles of that summer: given the highlights reels, the Champions League showings, and the incessant gossip linking him with all manner of clubs, why were Lyon so content to let him go? It quickly transpired, and in his final match against Morecambe he was booed off by his own fans.
Richarlison
Spending any less than the £60m it took to sign Richarlison was out of the question, particularly with the knowledge that Harry Kane was likely to leave the following summer.
If anything the mistake was not to spend more. Before Solanke he was the only natural centre-forward but injuries have restricted him to 73 appearances in two-and-a-half years, with a tally of just 16 goals. The bulk of them (12) came in 2023-24.
Giovani Lo Celso
Without a recurring hip injury, Lo Celso might have been a long-term Christian Eriksen replacement. Lo Celso loomed in the background, with spectacular performances for Argentina, but no Eriksen pretender really materialised until James Maddison joined in 2023.
Bryan Gil
Gil arrived looking like a young Ringo Starr, only for his time at Tottenham to consist of the defence lumping the ball in the air at all 5ft 7ins of him and wondering why he ended up on loan three times.
On not one of those occasions has he gone to a lower-half Premier League club or a Championship side who might help him acclimatise, but always back to La Liga.
Manor Solomon
Solomon has thrived on loan at Leeds, where he already has three more goals than the zero he managed from out wide at Spurs. The 25-year-old was another badly affected by injuries; tragic irony was that he could have been so much more, with reinforcements desperately needed on the left.
Alejo Veliz
The only striker signed the summer Kane departed, and on a six-year deal rising to £13m. He came from Rosario Central, Messi-land, on the same day as Van de Ven.
At the time, he was just 19 and was never intended to replace the irreplaceable, but he has spent most of his time since on loan with Sevilla and Espanyol.
Matt Doherty
Doherty is another over whom the frustration is that it could have worked so well. Able to fill in on the left and at wing-back, on paper he should have been ideal for the systems of Antonio Conte and Postecoglou.
Bizarrely, Spurs did not even receive a fee when he joined Atletico Madrid and his contract was terminated on deadline day in January 2023, because Spurs had already hit a quota of eight players out on loan overseas that season.
Carlos Vinicius
Vinicius was scoring more than a goal every other game at Benfica but struggled to settle in London over his loan spell, scoring just once.
Ashley Phillips
Were Tottenham’s centre-backs fit, it would have been impossible to keep them all happy; Radu Dragusin’s vocal agent has made that plain enough.
Phillips was sent to Stoke on loan this season to gain experience but is now watching from Stoke as his position is pinned on Archie Gray, a full-back a year younger than him. He could not have been recalled until January at the earliest, so too late to effectively cover for Spurs’ festive headaches.
Joe Rodon
Rodon was another long-standing young target, bought at the age of 22 for just £11m on the basis of his displays for Swansea in the Championship. In his first season, he was an unused substitute in 29 league games, vying with Davinson Sanchez for his spot.
He could not even be named in the Europa League squad because he counted as a non-homegrown player (being Welsh-federation trained). Most of his fee was recouped when he joined Leeds but it was a wasteful episode.
Ivan Perisic
A Conte signing if ever there was one – unlike Djed Spence, whom the Italian dismissed as no more than a “club” addition (publicly, too). Perisic certainly fitted into the category of “players you don’t have to Google” (hat tip to Danny Rose) but the deal seemed incongruous with the strategy as a whole, even if it was a free transfer.
The Croatian international impressed in bursts but suffered with injuries. Having been a natural fit for Conte’s system, working together at Inter Milan, inevitably his role was redundant when Conte left.
Arnaut Danjuma
After Spurs went to such lengths to pip Everton to his signing on loan from Villarreal, by the end of the same year he was at Goodison Park anyway – having produced one league goal in his nine appearances despite a promising start at Preston in the FA Cup.
Emerson Royal
Then 22, Emerson was both Brazilian and came from Barcelona, which made it a promising signing at just £25.8m as a replacement for Serge Aurier. What transpired was a string of defensive issues, a lack of clarity about his role further up the pitch, and an exit to AC Milan in the summer.
Clement Lenglet
Lenglet similarly fell into the category of Barcelona-bought, who might have been part of a serious rebuild from Conte – signed the same summer as Perisic, Richarlison and Yves Bissouma.
The major plus was that he could play at centre-back or on the left, but he never fully convinced at either.
Gedson Fernandes
Jorge Mendes was Gedson’s agent at the time, and Jose Mourinho the Tottenham Hotspur manager. Thus it had to happen, like it or not, and the young midfielder only ever got to make seven appearances.
Timo Werner
There are reasons to advocate for Werner; he stretches the play, has pace, and it is perhaps unfair to judge him by goals when he was not necessarily signed for a conventional role.
At any rate his initial loan has been extended, with an £8.5m option to buy that now looks unlikely after Postecoglou spectacularly threw him under the bus for another “unacceptable” performance against Rangers.
Jack Grealish
And the deal that never was. Surprisingly, really, given the generous offer of £3m and Josh Onomah, which rose to £25m when it was turned down. Grealish was still in the Championship with Aston Villa, It was 2018, he was 23 and yet to hit the heights he later managed – there were ample glimpses of his potential nonetheless.
It was short-sighted not to move while he was desperate to return to the Premier League. Within three years at £100m, he was out of reach and however much he is linked with Spurs now, he is likely to be again – unless Manchester City are willing to take a huge loss.
