The £146m Tottenham transfer gamble that did not pay off

Tottenham's policy in recent decades has always been clear in signing young players they believe can become stars and while that has brought some huge successes it has also brought some misfires.

Spurs' policy to mostly buy young has brought some spectacular successes in the past such as Dele Alli, before him Aaron Lennon, Kyle Walker, Christian Eriksen and certainly in terms of service to the club Ben Davies, while in more recent years Micky van de Ven, Lucas Bergvall, Destiny Udogie, Pape Matar Sarr, Archie Gray and in the end Djed Spence among others are looking like they could contribute in the long term to the club, having already all become trophy winners.

With 18-year-old Luka Vuskovic about to arrive at the north London outfit and Tottenham about to sign another centre-back in 20-year-old Japan international Kota Takai, the club's desire to build with youth shows no signs of abating. Striker Oliver Boast, who only 16 last month, is set to move from Leeds United this summer as well.

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The gamble of signing youngsters with potential is that not all of them are going to achieve what you hope from them and instead can end up costing plenty of money in the process. Here's a look at some of the Tottenham transfer misses with young players over recent years and it's worth pointing out that certainly not all are the club's fault but also not all are the players' faults.

We're looking specifically at players who were signed at the age of 22 or under and we've gone back over the past six seasons or so.

Bryan Gil

It's a shame it hasn't worked out for the young Spaniard but in truth Gil has never looked that comfortable away from his native Spain. Tottenham signed him from Sevilla as a 20-year-old for £21.6million with Erik Lamela going in the opposite direction in 2021.

The pretty dreadful nature of the transfer was only highlighted a couple of years later when Spurs sent Gil back on loan to the La Liga club, meaning the Spanish side had received almost £22million and Lamela only to have Gil still play for them. He has also been loaned out to Valencia and most recently Girona - you can see the Spanish theme.

Former managing director of football Fabio Paratici pushed hard for the signing of the Spaniard, but while he's a talented young player, Gil just doesn't have the physique for the Premier League at this point and perhaps never will. He has a year left on his contract at the club and is expecting to leave this summer. As with most of their unsuccessful deals, Spurs look set to lose a fair whack of money on the player, who is currently recovering from knee ligament surgery and only played 43 times for the club, scoring no goals but providing two assists.

Alejo Veliz

Spurs signed Veliz as a 19-year-old from Rosario Central for a reported £13million on the same day they brought in Van de Ven for three times that figure in 2023.

Veliz has played only eight times for Tottenham since that day, scoring once, with a dreadful loan to Sevilla - yes them again - and then a better loan to Espanyol, albeit mostly with appearances from the bench.

football.london understands that all the talk from Argentina about bids made and an advanced move for Veliz with clubs like Racing is only media noise from his homeland as of this moment and Spurs have not received a concrete bid.

They will accept a reasonable offer though for a player who currently does not appear good enough to break through into the Tottenham first team set-up.

Ashley Phillips

You never know, there could be a major turnaround this summer for Ashley Phillips under Thomas Frank but it looks unlikely with the number of centre-backs at the club and Vuskovic and Takai now joining.

Phillips was signed in 2023 as an 18-year-old from Blackburn after his £2million release clause was activated. However, two years on and he has not played a single competitive game for Tottenham despite impressive loans at Plymouth and Stoke.

This is certainly not a case of ability but more the wrong player at the wrong time, although with his much smaller price tag, Spurs will likely end up making a profit on Phillips when he does head off.

Joe Rodon

All the talk that summer in 2020 was that Mourinho wanted the experienced Milan Skriniar but eventually ended up with then 22-year-old Joe Rodon on a deal from Championship side Swansea worth up to £15million.

That was no slight on Wales international Rodon who has gone on to show that he's a very good centre-back and has led Leeds into the Premier League for the coming season with his performances. However, it was an example of Spurs taking the younger route and it not working out.

Rodon was just two games short of 100 appearances for Leeds in two seasons, whereas at Tottenham he managed only 24 appearances over four years amid loans to Rennes and then to Elland Road.

Tanguy Ndombele

Signed as a 22-year-old in a deal that could have been worth more than £60million overall and without doubt Tottenham's biggest flop of the modern era. Many speculate that the signing of the Frenchman, who promised so much but delivered so little for a string of managers, burned the club somewhat in taking bigger financial risks on younger, less guaranteed performers.

Signed in 2019, Spurs had to come to an agreement with Ndombele to end his contract early just to get his big wages off the books and he departed with only 91 games for the club under his belt, with 10 goals and nine assists as well as three loan spells to attempt to move him on earlier.

Either the scouting behind the move was dreadful when all of his former coaches spoke about issues with desire and drive, or Pochettino just felt he could be the man to change Ndombele. The Argentine didn't really get the chance to do so before being sacked and then Mourinho for a spell was the only one to get a tune out of him.

Ryan Sessegnon

This was purely down to injury rather than ability or drive. Sessegnon was signed as a 19-year-old for £25million from Fulham with Josh Onomah heading in the opposite direction in that costly summer of 2019.

Unfortunately the teenager arrived with a hamstring injury and never really shook them during his time at Spurs, in fact a successful loan away at Hoffenheim was probably his most pain-free period. Sessegnon played 57 times for Tottenham in all, scoring three goals and recording four assists, and it was heart-breaking to watch the constant breaking down with new hamstring injuries.

It got to the stage where the club didn't even take up the final year option on his contract and allowed him to leave for nothing last summer. Following surgery on the hamstrings in both legs, Sessegnon went back to Fulham and thankfully enjoyed a better season without any real injury concerns and hopefully he is on the right road now again.

Jack Clarke

Another part of that infamous summer of 2019, Spurs signed Jack Clarke as an 18-year-old for around £10million only for Pochettino to say the player wasn't ready for his team, so they had to send him back to Leeds, who had too many loan players to actually use him much.

That mess pretty much summed up the teenager's time at Tottenham with further loans at QPR and Stoke before the move to Sunderland that finally ignited his career.

Clarke left Spurs in 2022 for a permanent move to Sunderland and thankfully his career has continued on a mostly upward trajectory since with a move to the Premier League and Ipswich, albeit the Tractor Boys swapping places with Sunderland in the Championship next season. Clarke would play only four matches for Tottenham during his time in north London.

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