10 overpriced transfers that absolutely worked out

Harry Maguire

It’s said, usually by a writer searching for an intro, that there’s an ancient Chinese curse which proclaims: ‘May you live in interesting times.’ With Harry Maguire about to join Manchester United for £85m (opens in new tab), these are interesting times, and the buyers in today’s overinflated market are realising why that’s meant as a curse.

Unfortunately, the phrase is a myth. No such purported pearl of wisdom has been found in Chinese writings. And it’s similarly apocryphal that a gigantic price tag weighs so heavily on a footballer that they’re doomed to subsequently fail. Plenty do, of course. Andy Carroll, for one. 

These big-money signings weren’t mere eyebrow-raisers. They were proper whisky-tango-foxtrot moments that caused people to shake their heads and mutter that most damning of indictments: “Game’s gone.” In these instances, though, the game hit new heights...

Virgil van Dijk – Southampton to Liverpool, 2018 (£75m)

Where else to start? As 2017 became 2018, Liverpool used their All Saints loyalty card to buy Van Dijk for £75m. The world-record fee for a defender took their donations to Southampton north of £165m within three-and-a-half years. What madness! What extravagance! What… an extremely smart transfer, which in hindsight resembles genius.

Van Dijk didn’t improve Liverpool’s defence; he transformed it. They’d shipped 42 league goals in 2016/17 and were conceding an average of 1.21 goals per game in 2017/18, before Van Dijk’s debut. For the rest of the season, that dropped to 0.66, and in 2018/19 it was a scarcely believable 0.58.

Their 22 goals against represented the second-fewest in Premier League history – mostly thanks to Van Dijk and new goalkeeper Alisson, another player who repaid a huge transfer fee (£66.8m) that turned heads in the media and stomachs at Old Trafford.

Liverpool broke the taboo of investing heavily in a defender. Now, Maguire – a good centre-half but unquestionably inferior to the Dutchman – will likely cost yet more. Van Dijk raised the stakes.

Didier Drogba – Marseille to Chelsea, 2004 (£24m)

Didier Drogba Marseille

Jose Mourinho bought several players twice and managed Ricardo Carvalho at three clubs, but Drogba was his most quintessentially Mourinhesque signing. He knew exactly what and who he wanted; he told his chairman that the purchase was essential (“I said, ‘Mr Abramovich, pay – pay and don’t speak’”); and he spent big to secure the deal.

But, boy, did Chelsea get a lot for their £24m. It was a king’s ransom in 2004, especially for a 26-year-old who wasn’t a household name and who’d cost Marseille only £3.3m a year earlier (and Guingamp just £80,000 some 18 months before that). l’OM didn’t want to sell Drogba, but... well, you can’t argue with a £20m year-on-year profit. 

Chelsea, meanwhile, got a world-class line-leader who allowed Mourinho to dispense with a second striker. Drogba stayed for nine seasons and won them the Champions League. Bargain. 

Dani Alves – Sevilla to Barcelona, 2008 (£28.5m)

The upfront fee was actually £23.5m, with Barcelona promising Sevilla an extra £5m if Alves should end up playing a lot and winning a lot. Lifting 16 major trophies means he probably did just enough. 

The Telegraph, acknowledging disappointment for rival suitors Manchester United and Chelsea, called the transfer “astonishing”. It was a huge fee, all right, but Alves helped to regenerate not just Barcelona but the role of a wide defender. Nobody accused Pep Guardiola of spending too much money on full-backs ever again.

Jamie Vardy – Fleetwood to Leicester, 2012 (£1.7m)

As above, Vardy’s initial transfer fee was lower yet substantial: £1m, a record amount for a non-league player. It seems likely that Leicester did end up paying that extra £700,000 in add-ons which had allowed them to gazump Cardiff, though it’s possible Fleetwood didn’t add a ‘Premier League champions’ clause when Vardy left them for Championship football. Fools.

Paying a seven-figure sum for a 25-year-old with zero Football League appearances was bold from Leicester, but it paid off rather well. 

Fleetwood, meanwhile, received a bonus every time Vardy played for England and they’ll pick up another 20% to 33% (reports differ) of his next transfer fee, which makes his international retirement and refusal to leave Leicester look pretty bloody ungrateful.

Yaya Toure – Barcelona to Manchester City, 2010 (£24m)

Yaya Toure Barcelona

“The Ivorian is an average player who’s rumoured to be on £200,000 a week! Does he score goals? No. Does he create them? No. Is he an OK holding midfield player? Yeah – but De Jong, Vieira and Barry do that job already!” Paul Merson, there, giving the transfer a 2/5 rating.

Yaya Toure is considered one of Manchester City’s greatest ever players.

Kevin De Bruyne – Wolfsburg to Manchester City, 2015 (£55m)

Over to Merse again, this time in conversation with Jeff Stelling and Phil Thompson:

PT: “De Bruyne… my goodness, Jeff. The world is going mad, isn’t it? The amount of money they’re paying for this boy is absolutely bonkers [...] He’s a good player, but is he a great player? Wolfsburg are a good team, but come on.”

JS: “Merse, was Jose Mourinho wrong to let him go?”

PM: “I didn’t think so. I didn’t think he’d done it at Chelsea [...] There’s players you see and you think, ‘Yeah’ – I just don’t see this. I don’t see £50m-odd for this player. I really do not see it at all. And this is someone who was at the top club in England and didn’t click. He’s played here before at a top team, with top players. Honestly, Jeff, I thought it was lire.”

As laughable as that exchange is now, Thommo and Merse were only exaggerating what many were thinking. Manchester City were perceived to be overpaying for De Bruyne, having also just paid £44m, rising to £49m, for Raheem Sterling (who could be on this list, except a 20-year-old English forward with over 100 Premier League and Champions League appearances was never going cheap). But City were rewarded for laying the groundwork for Guardiola before he arrived. 

Gianluigi Buffon – Parma to Juventus, 2001 (£32.6m)

This one actually was in lire – 100 billion of the buggers, thanks to the wonderfully mad denominations of Italy’s former currency. 

Italy had officially adopted the euro two-and-a-half years previously, yet cash payments remained in lire until 2002. This suggests Juventus may have paid for the world’s most expensive goalkeeper – a title Buffon would hold throughout his 17 years in Turin – by giving Parma 100 billion coins, as well as another 67,484,662,576 in shrapnel for Lilian Thuram, the world’s most expensive defender at £22m. No wonder Parma went bust, carrying around that lot.

Trevor Francis – Birmingham to Nottingham Forest, 1979 (£1m)

Trevor Francis Nottingham Forest

Was it £999,999 or a million? Or even more? And, once Brian Clough had got his man, did Francis live up to the billing of being football’s first million-pound player?

In short: no. Francis did, however, win Nottingham Forest their first European Cup by scoring the final’s only goal, not long after arriving. Job done, really.

Christian Vieri – Lazio to Inter, 1999 (£32m)

Put away your hindsight goggles and it seems baffling that Inter would pay a world-record fee for a striker who’d played for six clubs in six years, in a sort of anachronistic tribute to 2014’s Shane Long. 

But, even if six seasons with the Nerazzurri brought him just one trophy (the Coppa Italia), Vieri repaid Inter’s faith with a ludicrous return of 103 goals in 144 league appearances. Not quite like Shane Long, then.

Jordan Henderson – Sunderland to Liverpool, 2011 (£20m)

It’s easily forgotten that a) £20m was still a big deal in 2011, and b) Henderson had to wait six or seven years for the respect he’s given now. When he was put alongside Lionel Messi on the cover of FIFA 16, the internet combusted with abuse, despair, banter and boycotts.

Returning to today, who most recently captained his side to Champions League glory? It’s not Messi. Nor is it Phil Jones, who moved to Manchester United in the same week Henderson joined Liverpool, for a similar fee, at a similar age, with greater potential being attached to his name. Nope – it’s Jordan Brian Henderson. Up yours, gamers!

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Huw was on the FourFourTwo staff from 2009 to 2015, ultimately as the magazine's Managing Editor, before becoming a freelancer and moving to Wales. As a writer, editor and tragic statto, he still contributes regularly to FFT in print and online, though as a match-going #WalesAway fan, he left a small chunk of his brain on one of many bus journeys across France in 2016.