Manchester United could set a new record for the biggest sell-on fee received if Mason Greenwood gets his £60m move. Even Chelsea would be jealous.
That Greenwood deal really could be huge for Manchester United this summer.
5) Dominic Solanke – £7.2m
It is vanishingly rare for any transfer to have been completed in the last two decades without a Michael Edwards clause inserted which in some way benefits Liverpool.
Their modern success has been built on the foundations of prescient sales, impactful signings, add-ons and perhaps soon even buy-backs as they safeguard and future-proof their position at the forefront of the market.
Liverpool had one such option on Solanke but little reason to explore it for years after he left to join Bournemouth. Only 18 months after the England international moved to the south coast, the Cherries were relegated to the Championship.
That arguably accelerated Solanke’s development. Two seasons in the second tier produced 44 goals in 16 assists in 86 appearances as he rediscovered his scoring touch and refined his overall game.
But it was the appointment of Andoni Iraola which really moved Bournemouth and Solanke to the next level. The 2023/24 season marked his first Premier League hat-trick and Player of the Month award, attracting interest from Spurs.
Liverpool could have hijacked that club-record deal but they preferred to sit back and wait for a healthy pay-out to land in their bank account courtesy of a clause entitling them to 20% of any profits Bournemouth made on his sale.
If they had anything about them, the Reds would have engaged in a bidding war before pulling out to artificially drive up the price and their subsequent proceeds. Edwards was probably busy fiddling with the aircon.
4) Michael Keane – £7.5mAs former reserve team manager Warren Joyce once had it, Keane “played against Real Madrid on a pre-season tour and Gareth Bale gave him a bit of a chasing,” so Louis van Gaal decided against integrating him into the first team.
It was very much the spiritual contrast to Cristiano Ronaldo giving John O’Shea the runaround.
A few loans later and Keane was sold to Burnley for £2.5m, much to Joyce’s disappointment.
“To be fair to Van Gaal, I met him in a bar in Portugal after he’d left and he said ‘you were right about Michael Keane, I was wrong’,” Joyce added in an interview years ago, by which point Keane had moved on to Everton for a cool £25m.
Manchester United raked in a decent amount as a result but they were actually favourites to sign Keane themselves when the auction commenced in summer 2017.
Jose Mourinho instead settled for Victor Lindelof, who would outlast the Portuguese and about seven other managers at Old Trafford.
3) Raheem Sterling – £9mIt goes down as the biggest Academy sale in Liverpool history but the role of QPR cannot be airbrushed from Sterling’s story.
The Hoops picked him up as a 10-year-old and navigated interest from far and wide well into Sterling’s teenage years, going as far as considering giving the forward a first-team debut at 14.
But his departure was inevitable and Liverpool were the only club willing to offer £500,000 up front with up to £2m more in bonuses.
That deal was ratified during the reign of Rafael Benitez, with Sterling breaking through under Kenny Dalglish before flourishing due to the threat of being sent on the first plane home by Brendan Rodgers.
After three seasons in the Anfield first team delivered a monumental title bottling as its peak, Sterling engaged in a bitter and controversial exit plan culminating in rejected contract offers, two snubbed Manchester City offers and the withdrawal from a pre-season tour squad and two days of training due to an apparent illness.
The £49m Liverpool eventually held out for made Sterling the most expensive English footballer in history at the time, while securing QPR some extra funds on top of the parachute payments they would soon receive due to relegation.
2) Kevin de Bruyne – £10mIt is often held as one of Chelsea’s biggest transfer mistakes but things could actually have been far worse.
And ever the politician, Mourinho made it sound like a masterclass in problem-solving and negotiation.
“If you have a player knocking on your door and crying every day that he wants to leave then you have to make a decision,” he said in summer 2015, shortly before Wolfsburg made a gargantuan profit on the deadwood they inherited from Stamford Bridge 18 months prior.
“I think Chelsea did a very good job. If De Bruyne stayed here, not happy, not motivated, wanting to leave, he stays here one more year and then we sell him for less than 50 per cent what we sold him for. In that moment it was very good business.”
If selling De Bruyne immediately or after another year were indeed Mourinho and Chelsea’s only options then it is difficult to argue they took the wrong course.
But one-and-a-half seasons in the Bundesliga were more than enough for De Bruyne to prove his worth and improve his value, to the extent that Chelsea’s add-on actually exceeded the fee they paid to sign the Belgian from Genk in the first place.
1) Tino Livramento – £15mChelsea are particularly well-versed in the art of selling players and engineering the majority of those deals to benefit them eventually.
There might not be many Academy graduates who make the grade for the Blues but Chelsea have enough alumni dotted around – and stocks in most if not all of them – to take advantage somehow.
“It’s probably the best academy in the world that anyone would want to go to and develop,” Livramento himself said when he took his diploma to Southampton. “Maybe one day,” he added of the prospect of Chelsea activating a £50m buy-back clause.
That never made sense after 34 appearances and an injury-disrupted spell on the coast, but Newcastle were willing to take the £32m plunge in August 2023.
A sliding sell-on clause meant Chelsea were due almost half of that sum, meaning an initial £5m sale ended up netting them £20m in the long run.
They will get nothing if and when Newcastle sell Livramento for £80m this summer.