Arsenal star with Chelsea pair in £116m list of Premier League stars regretting their summer transfer
Riccardo Calafiori to Arsenal? Kiernan Dewsbury-Hall to Chelsea? Seriously, what were these six Premier League stars thinking in the summer?
Tosin Adarabioyo (Fulham to Chelsea, free transfer)
When looking for players to ‘grace’ this list, it felt inevitable that a couple of Chelsea newbies would be included. It’s just basic maths.
We start with former Fulham centre-back Adarabioyo, who reportedly snubbed Big Eight rivals Manchester United and Newcastle United to become Chelsea’s first summer signing under Enzo Maresca.
The 26-year-old’s performances for Fulham in the Premier League made him the belle of the ball at the start of the summer window after he decided to run down his previous contract and leave as a free agent.
From Chelsea’s perspective, this was an uncharacteristically sensible and risk-free signing as they have acquired a handy squad player to take Trevoh Chalobah’s back-up role.
But for Tosin, this is quickly proving to be a poor move as one of the few things stable about Chelsea this season has been their centre-back pairing of Levi Colwill and Wesley Fofana.
Barring injuries, it is hard to see a route for Adarabioyo into the starting XI as his only appearances so far this season have been starts in Europa Conference League qualifiers and an outing off the bench against AFC Bournemouth on Saturday night.
I’m sure the money is lovely (especially with his unnecessarily lengthy contract), but it is probably only a matter of time before he joins a host of other unfancied Chelsea players in the bomb squad.
Riccardo Calafiori (Bologna to Arsenal, £33m)
Arsenal showed against Tottenham Hotspur that they have the best defence in the Premier League and their stoicism at the back will be required at the weekend when they travel to the Etihad to square off against title rivals Manchester City.
Mikel Arteta and Edu further boosted their defence with the signing of Italy international Calafiori in the summer, but his career at Arsenal has not got off to the best of starts.
After making two substitute appearances before the international break, the 22-year-old missed the North London derby with a calf problem.
This obviously could change as the 2024/25 season progresses, but Arteta’s first-choice defence feels pretty set in stone. In Calafiori’s absence, Timber solidified his position with a stellar display in Arsenal’s win at The Tottenham Hotspur Stadium, which should ramp up the Ange Postecoglou sack talk.
Calafiori was right to snub Chelsea’s reported hijack attempts and his versatility will come in handy for Arsenal in what’s bound to be an arduous season. But at best, he’s looking at around 10-15 Premier League starts in his debut season and this is not close to what he would have envisioned when he put pen to paper on his move to the Emirates.
Kiernan Dewsbury-Hall (Leicester City to Chelsea, £30m)
Maresca’s summer reunion with former Leicester City star Dewsbury-Hall meant the inexperienced head coach had at least one player on his side ahead of his debut season at Stamford Bridge.
As superb as Dewsbury-Hall was for Leicester in their Championship title-winning campaign, a move to Chelsea felt shoehorned and his unimpactful start to the season suggests were were right.
Although you can argue Dewsbury-Hall is a more attacking option, him and Conor Gallagher are pretty similar midfielders and it was a wasteful exercise to replace the Englishman as the £30m summer signing (and his predecessor) are/were equally as unlikely to have a prominent role at Chelsea this season.
Maresca’s start to life at Chelsea has not been as disastrous as it easily could have been, but he remains more likely to be sacked this season than he is to stay and if Dewsbury-Hall isn’t fancied now, his situation will presumably get even worse when yet another new head coach enters the scene. He’d have been better off joining Brighton instead.
Jake O’Brien (Lyon to Everton, £17m)
Oh, Everton…
I was foolishly among the F365 mob to back the Toffees to have a decent final season at Goodison Park after what I suspected was a positive transfer window.
But the pre-season optimism surrounding Everton was massively misplaced, with Sean Dyche already on the plank amid a start to the season which has plunged supporters into an even deeper state of misery, while the board considers a ‘sensational return’ in the dugout.
O’Brien is one player who can’t be blamed for Everton’s depressing start to the season and he may low-key be quite glad that he’s been out of the firing line.
The Republic of Ireland international has been behind Michael Keane and James Tarkowski in the pecking order, with his role set to be diminished further once Jarrad Branthwaite returns from injury.
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Jaden Philogene (Hull City to Aston Villa, £18m)
Unai Emery’s side used buy-back clauses to their advantage this summer as they re-signed Philogene and Cameron Archer.
While the latter was sold twice in the window as he joined newly promoted Southampton, Philogene has stuck around following his stellar season with Hull City in the Championship.
The flashy 22-year-old was one of the standout attackers in the second flight and had several Premier League clubs sniffing around him at the start of this summer; Ipswich Town were among the frontrunners for his signature until he opted to return to Aston Villa.
Philogene snubbed the unknown by returning to familiar surroundings at Villa, but this was foolish as he’s only been on the pitch for 17 minutes so far this season.
The lure of Champions League football is understandable, but the youngster is unlikely to feature much in the elite club competition or Premier League, so a move to a lowly top-flight team to continue honing his craft while playing regular football would have been a better fit.
Aaron Ramsdale (Arsenal to Southampton, £18m)
There comes a time when you have to think that Ramsdale is a sucker for feeling the pain of relegation.
The England shot-stopper already has two Premier League relegations on his CV from his time at AFC Bournemouth and Sheffield United and he’s very, very likely to suffer his third with Southampton this season.
Ramsdale was unfortunate to lose his starting place at Arsenal, but David Raya’s sensational performances since replacing him have justified Arteta’s brutal decision.
The same cannot be said for his outspoken father, but the 26-year-old barely put a foot wrong for Arsenal, so his performances for the north London outfit suggested he was good enough to be the No. 1 at most Premier League clubs.
After being heavily linked with Newcastle United, Ramsdale raised eyebrows by joining Southampton, who have done nothing to alter the perception that they are strong favourites for relegation.
Last season was torrid from Ramsdale’s perspective, but he left Arsenal with his reputation largely intact and it’s hard not to feel that he could have done better than this extremely underwhelming transfer.
