The top 10 players that clubs should never have allowed to leave - including Man Utd and Chelsea mistakes

With Christian Pulisic leaving Chelsea for AC Milan for a relatively cheap £20m, it’s impossible not to wonder whether this will be another gifted player that the West London club live to regret selling. How many times have they deemed a player surplus to requirements only for them to go on to star status elsewhere? They’ve got form, put it that way.

Of course, they’re not the only team who have binned a player only to be proved spectacularly wrong some time later. These are the top 10 players who discarded, forced out, released on a free or simply sold on because their club didn’t realise just how far they could go. All of them were unwanted when they should have been treasured. These are the sales that their former teams would turn the clocks back on in a heartbeat, were it but possible…

10. Sébastien Haller – West Ham United

Purchased for a club record £45m in 2019, Haller never hit his straps with the Hammers and managed just 10 league goals across 48 games – not a great return, by any standards. Any patience that the club may have had was eroded by a strained relationship between the Franco-Ivorian forward and David Moyes and the cord was cut in 2021, with Haller sold to Ajax at a huge loss. Still, he hadn’t looked great, had he?

Unfortunately, all recent evidence suggests a major misjudgement. Haller shone in Amsterdam, scoring 47 goals in 66 games, form which earned him a move to Borussia Dortmund, where he has started at a canter with nine goals in 19 games since his recovery from testicular cancer. A case of a square peg in a round hole at the London Stadium, perhaps, but West Ham clearly didn’t appreciate what they had on their hands either.

9. Paul Pogba – Manchester United

Pogba has veered from superstar to hopeless case and back again across the course of his rollercoaster career, but however you judge the totality of his career it’s pretty fair to say that Manchester United made a pretty big financial mess when they let him go to Juventus on a free as a 19-year-old back in 2012.

Regarded as a colossal talent at the time but also as a pain in the backside, and Sir Alex Ferguson took a very dim view of his attitude and demands for considerable amounts of cash to sign a new contract, so United happily waved him out of the door and allowed him to become somebody else’s problem. The issue was that Pogba was brilliant at Juventus, and United found themselves spending a cool £90m just to bring him back four years later. Apparently his contract demands weren’t quite so outrageous after all. A huge mistake in purely financial terms (see also Chelsea and Romelu Lukaku…).

8. Gaël Clichy – Arsenal

Selling Clichy to league rivals Manchester City for a relatively modest £7m seemed like a fairly strange decision at the time – but hey, they can use that cash to buy André Santos and Carl Jenkinson, right? The Brazilian and future Finnish international joined an up-and-coming Kieran Gibbs at the Emirates, so the Gunners looked pretty well set.

Which didn’t exactly prove to be the case, of course. Santos was a flop and was back in Brazil two years later, Jenkinson failed to live up to his early billing, and while Gibbs had a perfectly solid career, it’s fair to say that he didn’t reach the heights Clichy did – the Frenchman (who’s still playing in Switzerland, amazingly) went on to play an important role in City’s first two Premier League title wins and picked up a couple of League Cups too. Not Arsène Wenger’s finest piece of horsetrading.

7. Teddy Sheringham – Tottenham Hotspur

£3.5m wasn’t a massive amount of money for a striker, even in 1997, but nor did it seem like such a bad deal for a 31-year-old who’d only managed seven goals the previous season. Most pundits thought Sheringham was past his best, and Spurs probably thought they were fleecing Manchester United under the circumstances. They were not.

Sheringham wasn’t prolific throughout his United career but became a key part of their attack, remained a superb link-up striker and had the happy knack of scoring big goals in clutch situations, playing a substantial role in United’s treble-winning season. He was also still good enough to crack in 21 goals in the 2000/01 season, during which he turned 35. Just to hammer the point home, he came back to Spurs that summer and managed two more double-digit seasons for the North Londoners. Finally played his last game in 2007, a decade after Spurs deemed him too old to be worth clinging on to.

6. Serge Gnabry – Arsenal

To be fair to Arsenal, Wenger did apparently want to extend Gnabry’s contract in 2016, but wouldn’t give Gnabry the playing time he wanted – so after just 18 Arsenal appearances, the 21-year-old was flogged to Werder Bremen for a modest £5m.

Since then he’s racked up 81 Bundesliga goals, become a key player at Bayern Munich and scored nine goals in a victorious Champions League campaign. If Wenger had rated him highly enough to give him some more game time, then who knows how much better Arsenal could have been over what turned out to be some pretty barren years before Mikel Arteta took over.

5. Jaap Stam – Manchester United

United’s greatest boss though he may well be, Ferguson did have a bad habit of letting players go when they still had plenty to offer – usually because he’d fallen out with them. There may have been some of that in the sale of Stam, probably the best centre-back in the Premier League at the time but who had caused some unnecessary tension by publishing a tell-all autobiography – although an Achilles injury was the main reason. Ferguson simply judged that Stam wouldn’t be able to keep playing at the same level.

He was wrong. He went on to win the Coppa Italia with Lazio before reaching the Champions League final with AC Milan, one of the victims of that great comeback in Istanbul. Still playing brilliantly some five or six years later at Ajax, Ferguson would admit that “in playing terms it was a mistake”. At least he fessed up to that one.

4. Gerard Piqué – Manchester United

United and Ferguson again, I’m afraid. The young Piqué had made 12 league appearances for the Red Devils and was starting to generate some hype, only to be allowed to leave on a free transfer to return to Barcelona, where he had played most of his youth career.

Getting precisely zero pounds for a player who would go on to be one of the greatest centre-backs in European history doesn’t look too smart in retrospect – the Spaniard would go on to make over 600 appearances for Barcelona, starring during the greatest era in their history, and picked up over a century of caps for the national team. Along the way he nine league titles and more Champions Leagues than Ferguson managed in his entire career. Whoops.

3. Eric Cantona – Leeds United

Finally, a victory for Fergie. Cantona had a fractious end to his career at Leeds United, with a string of sub-par performances seeing him dropped by manager Howard Wilkinson as the Whites made something of a hash of their title defence. Fuming at being benched by his manager, Cantona went on strike, refusing to report for training and handing in a transfer request by fax. Unwilling to deal with the fiery Frenchman’s antics, Leeds allowed him to move to United for £1.2m, a fee which seemed a bit on the low at the time as well.

Cantona would, of course, be one of the first greats of the newly-incarnated Premier League, winning four league titles and two FA Cups as well as scoring a ton of spectacular goals. Granted, he was also largely responsible for allowing Blackburn Rovers to win the 1994/95 title when he picked up a hefty suspension for kicking a Crystal Palace fan in the stands, but his charismatic persona and elegant playing style made him a legend, and one who was probably worth a few bob more.

2. Kevin de Bruyne – Chelsea

Here we go – the Chelsea section. We know you’ve been waiting for it. Let’s begin with a certain young Belgian, signed for £7m and given precisely three Premier League games to show what he could do before Chelsea flogged him to Wolfsburg for £18m – hey, a pretty nice profit, that. No chance such a canny bit of business would come back to bite them, right?

Well, Manchester City dropped £55m on De Bruyne all of one year later, which should tell you that Chelsea might have slightly misjudged the market for him – and that alone would probably be enough to turn the decision into a clanger. Given that he’s since established himself as arguably the best attacking midfielder in the world and won practically everything, it looks less like a clanger and more like a whole planet’s worth of them, Soup Dragon included.

1. Mohamed Salah – Chelsea

To be honest, deciding which of these two transfers was worse is pretty hard. Salah arrived at Chelsea for a cool £11m from Swiss outfit Basel and at least got a little bit more of a chance than De Bruyne did – all of 13 league matches before he was farmed out on loan, impressing enough at Roma to persuade them to pay about £13m for him in 2016. The fact that Chelsea didn’t even turn that big of a profit on the trade is the main reason we’re sticking the Egyptian up at number one.

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Much like De Bruyne, Salah only took one year to prove he was worth a whole lot more cash. Liverpool’s deal was worth up to £43m, assuming all of the add-ons were triggered, which seems pretty likely. 186 Liverpool goals later and a whole string of records broken, and getting the money side wrong looks like the least of Chelsea’s problems. Letting one Premier League great slip through your fingers is careless. Two? Well, at least they’ve won the Champions League since, eh?