
Daniel Levy’s £12m mistake that highlights the worrying truth about Tottenham’s transfer business.
The 2018/19 season proved to be a memorable one for Tottenham for a variety of different reasons.
Reaching the Champions League final against all the odds after managing to hold on against Man City in the quarter-finals before then recovering from a 3-0 aggregate deficit against Ajax in the semis.
Spurs, unfortunately, couldn’t go all the way after Liverpool claimed a 2-0 victory in the showpiece finale in Madrid.
It was some achievement by Mauricio Pochettino’s side, especially as the club had failed to bring in new additions in both the summer and winter transfer windows..
It did appear towards the end of the summer market that Aston Villa’s Jack Grealish would be on his way to white hart lane with the Midlands club in need of the cash after losing out in the Championship play-off final against Fulham a few months earlier.
However, the move never materialised with Daniel Levy and Tottenham failing to submit an acceptable offer.
The then 22-year-old playmaker was reportedly disappointed that a proposed move to north London was turned Down. As reported by Skysport
He then remained at Villa, playing a pivotal role in their return to the top flight and helping establish them as a Premier League club once again.
Given Grealish departed Villa Park for Man City in August for an eye-watering £100million fee, Spurs’ failure to sign the England international is one that still deeply frustrates many Tottenham fans to this day.
Having a policy of signing talented youngsters who could develop and become a key part of the club’s future, Spurs were linked with Jarrod Bowen in 2018/19.
Making a name for himself at Hull City with ten goals before the turn of the year, the attacker hit a further four goals in January and was duly linked with a move to the Premier League before the transfer deadline, although Hull had made it clear their prized asset was not for sale.

Jarrod Bowen of Hull City during the FA Cup Fourth Round match between Hull City and Chelsea FC (Getty Images)
Spurs were one of those clubs mentioned in regards to a move for Hull’s exciting talent and the club had been keeping a very close eye on the player but it was then decided in a transfer committee discussion ahead of the transfer deadline that they would not make a move for him in the winter market.
Instead, they would continue to keep tabs on him and make a summer move if he continued to impress.
However, a move didn’t materialise, with Spurs decided to opt for Leeds young winger Jack Clarke over Bowen and completed a deal for a fee in the region of £10m.

Leeds United’s Jack Clarke during the Carabao Cup Second Round match between Leeds United and Stoke City (Getty Images,)
The new signing immediately returned to Elland Road on a season-long loan spell but only featured in three games before he was recalled by Spurs, whereas Bowen continued to shine for Hull and scored 17 goals for the Tigers until West Ham handed him his Premier League move in January 2020.
Taking a bit of time to adapt to the demands of the Premier League and find his top form after his £22m transfer, Bowen has hit another level under David Moyes and the Hammers are now seeing the very best of him.
The 25-year-old is in the form of his life and has duly put himself in a very good position to be called up to Gareth Southgate’s England squad for the very first time.
Jack Clarke has yet to feature for the Tottenham first team since his second-half cameo away at Pacos de Ferreira

Fernando Fonseca of FC Pacos de Ferreira with Jack Clarke of Tottenham Hotspur FC in action during the UEFA Europa Conference (Getty Images)
With Tottenham fans seeing Grealish as the one that got away in the summer of 2018 going on his form in the following few seasons, many will now be feeling the same way about Bowen with the West Ham ace putting himself on the edge of an England call-up.
Clarke, on the other hand, is currently playing for Tottenham’s under-23s and looks set for a loan move away from the club this month with no sign of breaking into the first-team picture.
The York-born attacker is also now in the final 18 months of his contract and that gives Spurs a big decision to make over him in the summer, thus raising the real possibility of him leaving without even making a single appearance in the Tottenham matchday squad for a Premier League game.
Speaking on the latest edition of Gold and Guest talk Tottenham, Gold reflected on the decision not to sign him and discussed his surprise that the club ultimately didn’t pull the trigger on the deal:
“I’m a big Jarrod Bowen fan as well, I still look back to the decision to go for Jack Clarke over him and kind of scratch my head completely.
And that’s no disrespect to Jack – Jack Clarke could still develop, get minutes somewhere and go on to be a very good young player.
“But if you look at it purely on paper and the impact of the two players, albeit ones of different ages, it looks like a no-brainer decision that should have been made.
Because I think Jarrod Bowen has shown that he’s a very good Premier League player.”
Tottenham’s decision-making in the transfer market, especially the summer of 2019, has been questioned recently and Grealish and Bowen highlight the point.
Having been given kudos for the signing of Dele Alli from Mk Don’s, Tottenham have however missed out on two of England’s most talented youngsters, Fabio Paratici and Spurs need to ensure it doesn’t happen again as it will only lead to even more questions in the future.