Tottenham had a pretty productive summer transfer window with Ange Postecoglou being backed again by Daniel Levy.
From the get-go, Tottenham brought back Timo Werner on a season-long loan deal, before going down the younger route.
Archie Gray was a standout purchase after the highly-rated teenager arrived from Championship side Leeds United and fans also got to see Lucas Bergvall for the first time after his move in the winter.
Spurs fans were pretty happy with these types of deals, including Wilson Odobert further enhancing the attacking line and Dominic Solanke being the club-record transfer deal.
But there were a lot of interesting deals made with the outgoings too and that’s where Darren Bent thinks the Premier League’s ‘worst signing’ lands.
Several senior and previously established players headed for the exit door, with Postecoglou making it clear that they weren’t part of his long-term plans given their lack of minutes.
Emerson Royal joined AC Milan, whilst Pierre-Emile Hojbjerg, whilst a leader out on the pitch and in the dressing room, left and joined Roberto De Zerbi in Marseille.
These players served the London club very well, but there is one individual who served them for longer and he meant a lot more to the fans.
Oliver Skipp, who came through the ranks at Tottenham, ended his near two-decade association with the club and joined Leicester City.
Ironically enough, hours before Leicester and Tottenham drew on the opening weekend of the new season, Skipp had finalised his £20 million move to the King Power Stadium.
But, for Darren Bent, and whilst he felt bad saying it, this is the ‘worst signing’ of the summer transfer window, as he told talkSPORT (03/09/24 at 5:45 pm).
Oliver Skipp’s transfer to Leicester City
“Worst signing, Oliver Skipp and I feel so bad saying that,” said Bent. Andy Goldstein responded: “You are a horrible man.”
Bent added: “What am I supposed to do? I just think £20 million. Is that what Leicester needed? Oliver Skipp and Harry Winks. Harry was good last year in the Championship.
“The reason why I am not putting Dewsbury-Hall (to Chelsea) in there because Chelsea have just thrown the money left, right and centre at loads of different players, so you almost get lost in it. I am not saying he is a bad player. Leicester fans can tell me, when they signed Oliver Skipp, did they automatically think ‘right, yes, he gives us the best chance of staying up?’ Does he?”
The right time for Oliver Skipp to move
Tottenham’s midfield was starting to get jam-packed and Postecoglou was hardly using the hard-hitting midfielder.
Some would argue, given Skipp’s defensive nature, then he should have stayed on board, especially given the injury issues the team could suffer and the fact that they are in Europe.
But, for the player himself, who will turn 24 later this month, the time is right to now start regular matches and try to find his level.
If he performs well and helps Leicester stay in the Premier League, then Darren Bent will be quickly eating humble pie.
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