If Florian Wirtz triggers enough of his add-ons to become a Premier League record transfer then he may find himself among some fine Manchester United deals.
**18) Andriy Shevchenko – £30.8m, May 2006 (AC Milan to Chelsea)**It was a dream transfer Roman Abramovich revisited in each of the four summers from his takeover of Chelsea to the belated capture of a Shevchenko past his prime at 29, carrying injuries and still psychologically broken by Jerzy Dudek.
The player himself cited the owner’s “persistence” and a change in his circumstances with the imminent birth of his second young son as the key motivating factors behind the move.
Milan president Silvio Berlusconi worded it slightly differently, saying that “his wife ordered him to London with their children where the fog will do their lungs the world of good”, and “when his wife shouts, he runs under the bed like a lap dog”.
That presumably made for an awkward reunion when Shevchenko and his fog-filled lungs returned to Milan two years after he left for a loan which only further underlined how far he had fallen; the Ukrainian added two goals in 26 games to his glittering record with the Italian giants.
Chelsea cut their considerable losses three years after making Shevchenko the most expensive footballer in British top-flight history, packing him back off to Dynamo Kyiv as a free transfer with as many Premier League goals as Gervinho in two more games.
**17) Juan Sebastian Veron – £28.1m, July 2001 (Lazio to Manchester United)**Youse are indeed f**king idiots, but it was revealing that within a year of that impassioned rant in support of “a f**king great player”, Veron had been sold to direct Premier League rival Chelsea for about half of what Manchester United paid to sign him two years before.
“You tell me what is wrong with Veron,” sounds more like a desperate plea to the bewildered journalists present than a defence of the Argentinean playmaker in retrospect.
Sir Alex Ferguson would later write that ‘he was an individual’, a ‘free bird’, a ‘wildcard’ who ‘went wherever he liked’ and ‘just couldn’t play in our team’. If only Roy Keane hadn’t been there.
**16) Robinho – £32.5m, September 2008 (Real Madrid to Manchester City)**“On the last day, Chelsea made a great proposal and I accepted,” said a clearly quite shell-shocked Robinho, the Blues having erroneously started to sell shirts with his name on the back before Manchester City marked their new takeover with a good old-fashioned transfer hijack.
By the admission of manager Mark Hughes, there was also “probably a grain of truth in the rumour that Robinho thought he was actually signing for Manchester United”.
But it was Manchester City the Brazilian blazed a trail for – for about three months. Robinho scored 12 of his 16 goals for the club between his arrival in September 2008 up to the end of that December, after which he soon faded from view before being completely phased out by Roberto Mancini.
Manchester City made about half their money back within a couple of years but it required a helping hand from AC Milan.
**15) Enzo Fernandez – £106.8m, January 2023 (River Plate to Chelsea)**There is plenty of scope for Fernandez to improve his standing with Chelsea, the Argentinean having already overcome his first few injury and Pochettino-shaped hurdles at Stamford Bridge.
This past season was the biggest step yet in the right direction as Fernandez established a more defined position, embraced a captaincy he should never have been awarded and inspired the Blues to Conference League glory.
A little more is needed to justify an absurd outlay but the good news is that Fernandez has time to do it with seven years left on his contract.
**14) Stan Collymore – £8.5m, July 1995 (Nottingham Forest to Liverpool)**Few could have expected that Collymore closing in would mark the peak of his record-breaking Liverpool move and arguably his trophyless professional playing career as a whole.
The raw numbers are far from shameful: 35 goals and 16 assists in 81 appearances for the Reds, who almost broke even when Aston Villa signed him in May 1997.
But the issues which would plague and ultimately prevent Collymore from realising his potential were already bubbling under the surface and the emergence of Michael Owen meant Liverpool quickly outgrew him.
**13) Paul Pogba – £93.9m, August 2016 (Juventus to Manchester United)**It might forever be the penultimate world-record transfer, considering just how ludicrously how the market-shattering bar was set by Paris Saint-Germain and Neymar a year later.
At least the French giants recouped a healthy percentage of that fee back; Manchester United managed to let Pogba go to Juventus for free twice while spending what remains a club-record sum to sign him in between.
There was a Europa League, League Cup and PFA Team of the Year place but viruses, haircuts, dancing and feuding with Graeme Souness – not all four with Souness, to be clear – defined most of a mutually disappointing six years.
**12) Moises Caicedo – £100m rising to £115m, August 2023 (Brighton to Chelsea)**The add-ons built into their embarrassing climbdown on Caicedo were described as eminently ‘achievable’. Some were related to European qualification with the rest thought to be tied to appearances.
If winning the Conference League, reaching the Champions League and making 95 appearances for Chelsea has not triggered those extra payments then it is only a matter of time.
It is entirely feasible that Caicedo ends up among the more illustrious names on this list. The 23-year-old has overcome some early teething problems to emerge as the all-action midfielder Chelsea thought they had signed and it is instructive how infrequently to fee is mentioned two years on.
**11) Rio Ferdinand – £18m, November 2000 (West Ham to Leeds)**The atrocity of a pundit has made it easy to forget the magnificence of the player. It is not worth thinking about how many times Ferdinand might have repeated ‘Ballon d’Or’ had he ever been able to egomaniacally watch himself from the stands instead of tapes of Phil Jagielka at his peak.
Leeds paid £18m for 18 months which feel like a forgotten footnote in Ferdinand’s career, but it was the perfect snapshot of how the club, in the immortal words of Peter Ridsdale, “lived the dream”: they finished fourth and fifth in the Premier League and reached the Champions League semi-finals, Ferdinand himself scoring in a win over Deportivo in the quarters.
“I’m satisfied I’ve done the best job for Leeds United,” said Ridsdale with no hint of sarcasm of self-awareness when explaining the sale of Ferdinand to a bitter rival soon after. “If you invest £18m and get £30m you’ve done a good job,” he added. Leeds supporters might disagree.
**10) Fernando Torres – £50m, January 2011 (Liverpool to Chelsea)**If bringing Gary Neville to climax at the Nou Camp automatically qualifies any signing as a success then Torres can look back on his Chelsea career with immense pride.
The Spaniard won three trophies with the Blues and played a significant part in the capture of each, so likely does not carry around the baggage of Stamford Bridge failure many have tried to saddle him with.
But it is startling that he both played 30 more games for Chelsea than he did Liverpool, and scored 36 fewer goals. Torres crammed nine goals into his final half-season with the Reds before moving in the winter of 2011; in his best league campaign for the Blues he only found the net eight times.
**9) Chris Sutton – £5m, July 1994 (Norwich to Blackburn)**Another whose punditry present masks a playing past, Sutton was good enough to become the highest-paid player in the Premier League for a time as the title-unlocking foil for Alan Shearer.
The 25 goals Sutton plundered in a Norwich title challenge which quickly faded remained his best career return in a season including even his Celtic stint, but that contribution to Blackburn’s ascent to the English top-flight throne was crucial.
**8) Jack Grealish – £100m, August 2021 (Aston Villa to Manchester City)**As eager as Manchester City are to write off their record signing four years after heartlessly plucking the free spirit from Aston Villa and meticulously teaching him how to pass backwards, it is important to remember what Grealish has achieved at the Etihad.
Only seven teammates played more minutes in their Treble season and just six supplied more goals and assists as Grealish was made the headline star of the celebrations, backing up his objective when leaving Villa Park: to “have as many winner’s medals as possible”.
Another Premier League title has since been added alongside a Super Cup and Club World Cup, but the more peripheral role Grealish played in those successes has only served to see him pushed out of the door entirely.
**7) Ruud van Nistelrooy – £19m, July 2001 (PSV to Manchester United)**“This signing demonstrates that Manchester United are a force in Europe,” said Manchester United chief executive Peter Kenyon of a deal Ferguson hoped would fill the club’s transfer remit of “improving the team by one or two per cent every year”.
Manchester United had won the Premier League title three seasons in a row but followed up Champions League glory in 1999 with a pair of quarter-final exits to Real Madrid and Bayern Munich, so the explicit reason for bringing in Van Nistelrooy could only have been to push them past that continental barrier.
Yet in Van Nistelrooy’s five seasons at Old Trafford, the club’s Champions League performance in chronological order – semi-final, quarter-final, last 16, last 16 and group-stage exits – coincided with the Dutchman scoring well over a goal every other game even with injuries.
A record of 150 goals in 219 appearances underlined his individual brilliance but it was eventually decided that it came at the overall expense of the team, especially when your Cristiano Ronaldos and the Wayne Rooneys of this world started to blossom.
**6) Alan Shearer – £3.6m, July 1992 (Southampton to Blackburn)**Shearer “felt the time was right to come to Blackburn” and few could have argued with his logic. With his choice of clubs as a 22-year-old coming off the back of a 20-goal season with Southampton, he sensed a shift in the sands with Jack Walker’s 1991 takeover.
Rovers had secured promotion under Kenny Dalglish and Shearer was earmarked as the ideal signing. In four seasons at Ewood Park he scored 130 goals in 171 games, delivering the Premier League title.
And the time was right for him to leave Blackburn when he did too; Shearer’s 31 goals were only good enough for 7th place in 1995/96 when he cashed in on his stock to secure his next move, and Rovers were relegated three years later.
5) Andy Cole – £7m, January 1995 (Newcastle to Manchester United)
A transfer so controversial Kevin Keegan felt compelled to defend it to fans on the steps of St James’ Park, Cole himself can have no regrets.
After 68 goals in 84 matches for Newcastle were only good for third place and some early cup exits, a breakdown in the relationship between Cole and Keegan meant their productive union was, in the player’s own words, “a bit of borrowed time”.
The optics were uncomfortable for Newcastle in selling to the enemy, but Cole made the most of his opportunity with five Premier League titles, two FA Cups – including one final won against the Magpies – and a Champions League.
**4) Alan Shearer – £15m, July 1996 (Blackburn to Newcastle)**Manchester United fans have spent the best part of the subsequent two decades imploring Shearer to cheer up and reminding him of the preposterous probably trophy haul he rejected not once but twice, but the all-time record Premier League scorer has always denied any regret he might have at joining the handful of world-class players to turn down Old Trafford and Ferguson.
Some might still see it as a hollow coping mechanism but for Shearer, the honour of becoming his boyhood club’s greatest ever scorer outweighs what he could have achieved at Manchester United.
And a dressing room containing both him and Roy Keane might well have imploded anyway.
**3) Dennis Bergkamp – £7.5m, June 1995 (Inter to Arsenal)**“I would have taken Stan Collymore ahead of Bergkamp, even for £1million more. Liverpool have got a better deal than Arsenal,” will forever stand as one of the great early Premier League quotes.
Stuart Pearce, then still playing for Nottingham Forest, went on to say “the odds” were “loaded against” Bergkamp “making any kind of impression in an Arsenal shirt” under a newspaper headline of ‘BERGY’S A WASTE OF MONEY’.
Seven goalless games seemed to back up the assertion that Arsenal had been fleeced when tripling their club-record transfer, but the Dutchman was soon flying on a route which would take him to six trophies, 120 goals and his very own statue.
**2) Rio Ferdinand – £29.3m, July 2002 (Leeds to Manchester United)**If signing Veron the previous year represented a gargantuan risk Manchester United could nevertheless afford, preying on the financial difficulties at Leeds to poach Ferdinand was anything but.
A 23-year-old with more than 180 career Premier League appearances to go with extensive international and Champions League experience was as close to a guarantee of prosperity as possible – and one of the best examples of a transfer ‘policy’ the club have revived.
The David Moyes season was regrettable and made Morgan Amalfitano seem like the world’s greatest player for a couple of minutes, but six Premier League titles and a Champions League speak for themselves.
**1) Roy Keane – £3.75m, June 1993 (Nottingham Forest to Manchester United)**It does not feel likely that a relegated player could prompt a British record transfer chase in the modern day but the culmination of the inaugural Premier League season saw future title rivals Blackburn and Manchester United engage in their first true battle.
Rovers would have won if their negotiations were concluded earlier on that fateful Friday afternoon. But with no-one in the office at Ewood Park to sort the paperwork, Ferguson swooped with a classic hijack.
The Scot might never have made a more important signing; it provided the foundations for glory which spanned generations, Keane leaving on typically bitter terms well over a decade later armed with seven Premier League titles, a Champions League and numerous other trinkets to potentially stick up Mick McCarthy’s arse or bollocks.