To be quite candid and direct, Oliver Skipp was not a good signing for Leicester City Football Club. That is the most simplistic and readable way of stating that fact.
Multiple elements combined to make that an ill-advised transfer; which are also rather easy and simple to explain. First of all, believe it or not, Skipp was damaged goods. The switch was seemingly doomed before he even arrived at the luxury Seagrave training complex, which has become a gift and a curse too, incidentally.
You see, Skipp is a lifelong Tottenham Hotspur supporter. The defensive midfielder reportedly grew of age watching the North London club, not to mention spending 18 years at their academy and making partial impact in the Spurs first team.
Having joined the capital side at the age of five, and subsequently making over one hundred senior appearances, he is inextricably tied to Tottenham. Once a Fox, he played for the East Midlanders during the 2024/25 campaign, but this writer is of the opinion that the Englishman would have preferred to stay at the Tottenham Hotspur Stadium, even as a utility man.
Skipp did not become much more than a backup man under a few separate managers on Filbert Way. Harry Winks, who has also seen his tenure at Leicestershire wind to a close, often took Skipp's role, though the pair ultimately played together occasionally as well.
Yet the 25-year-old failed to consistently impress whilst competing in the Premier League. Neither was he a particular, regular standout when playing in the EFL Championship.
Skipp was widely considered statistically disappointing and underwhelming from a fan perspective during his spell with City. However, his perception underwent a brief, localised transformation as time went on, though the label of "flop" is perhaps only mitigated by the fact that he was an earnest contributor during a difficult era.
Overall, the Harlow-born footballer was a disappointment; while the label of a total failure appears harsh, a £25 million outlay was fairly imprudent. Of course, considering the club's well-documented financial woes, Skipp is understandably in the shop window as the powers-that-be in LE2 attempt to be 'in the black', as opposed to 'the red'.
Leicester City can offload Oliver Skipp to Middlesbrough if they wise up
​Meanwhile another red, Middlesbrough, have supposedly expressed a clear interest in the midfielder as a potential replacement for their own departing personnel. Yet a £15m price tag slapped on him has reportedly deterred the Teesside club.
"Skipp is supposedly keen to depart, but Middlesbrough are said to have been deterred by a £15m price tag slapped on his head."The Yorkshire Post
This valuation is high. Though it is possibly necessary for Leicester's monetary recovery as well, highlighting the difficult position in which club and players find themselves.
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