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Arsenal may have to break the astonishing Moises Caicedo transfer record if they wish to secure Morgan Rogers from Aston Villa this summer.

Villa’s valuation of Rogers – who Arsenal are reportedly “close” to finalising terms with – stands at £130 million. The figure is significant, as it would hand the Villans a record-breaking sell-on fee, overshadowing all previous top 10 deals of its kind.

In recent decades, few transfers have gone through without a signature Michael Edwards clause that somehow benefits Liverpool. The club’s modern-day success has been founded on shrewd sales, smart acquisitions, clever add-ons, and perhaps soon, well-timed buy-back clauses designed to protect their long-term position in the market.

One such clause was tied to Dominic Solanke. Although Liverpool never exercised their buy-back option after he moved to Bournemouth, it proved lucrative later. Eighteen months after Solanke’s switch, Bournemouth were relegated to the Championship – a setback that turned out to be a blessing for his development.

During two seasons in the second tier, Solanke netted 44 goals and provided 16 assists in 86 matches, rediscovering his scoring form and fine-tuning his overall game. The arrival of Andoni Iraola as Bournemouth’s manager then propelled both player and club further forward. In the 2023/24 campaign, Solanke netted his first Premier League hat-trick and earned a Player of the Month award, drawing attention from Tottenham Hotspur.

Liverpool could have intervened in that record-breaking move but instead chose to wait for the windfall from a 20% profit clause inserted into the original deal. A more mischievous approach might have seen the Reds spark a bidding war to inflate the price, but as some quipped, perhaps Edwards was too busy adjusting the air conditioning.

Former Manchester United reserve coach Warren Joyce once recalled that Michael Keane “played against Real Madrid in a pre-season friendly and Gareth Bale gave him quite a chase,” leading Louis van Gaal to abandon plans to promote Keane to the senior side. It was a sharp contrast to Cristiano Ronaldo’s famous dribbling exhibition against John O’Shea years earlier.

After several loan spells, Keane was sold to Burnley for £2.5 million, a move that disappointed Joyce. “To be fair to Van Gaal, I met him later in Portugal and he admitted, ‘You were right about Michael Keane, I was wrong,’” Joyce later revealed. By that time, Keane had already joined Everton for £25 million, earning Manchester United a decent cut – though United had initially been favourites to re-sign him in 2017. Instead, Jose Mourinho opted for Victor Lindelof, who would go on to outlast several managers at Old Trafford.

Meanwhile, Raheem Sterling’s move remains the biggest Academy sale in Liverpool’s history, though Queens Park Rangers played a pivotal role in his early career. QPR scouted him at age 10 and resisted numerous offers before Liverpool finally paid £500,000 upfront with £2 million in potential bonuses. Sterling rose through the ranks under Kenny Dalglish and Brendan Rodgers before forcing a controversial move to Manchester City for £49 million – then a record for an English player – which also rewarded QPR thanks to a sell-on clause.

One of Chelsea’s most criticised transfers remains Kevin De Bruyne’s sale to Wolfsburg, though Jose Mourinho defended it as smart business. “If a player knocks on your door every day crying to leave, you have to decide,” Mourinho said in 2015. “If De Bruyne stayed unhappy, we’d have sold him later for much less. It was good business then.” De Bruyne’s subsequent rise in Germany, however, ensured Chelsea’s add-on payment exceeded what they had originally paid Genk for him.

Hull City’s final Premier League squad before relegation was full of future stars – Harry Maguire, Andy Robertson, Jarrod Bowen, Tom Huddlestone, and Shaun Maloney. Maguire was the standout performer, winning both Players’ and Fans’ Player of the Year before moving to Leicester City for £17 million. His later £80 million transfer to Manchester United made him the most expensive defender in football history, earning Hull a significant share of the proceeds.

Bristol City, who first recognised Antoine Semenyo’s potential, continue to benefit from his success. Having sold him to Bournemouth for £10.5 million in January 2023, they doubled their profit three years later when Bournemouth sold him again amid Manchester City’s transfer panic. Semenyo expressed gratitude, saying, “Bristol City believed in me from the start, and that will never be forgotten.”

Paris Saint-Germain, already dominant in every aspect of football, have also mastered the art of selling. Their record-breaking deals, such as Goncalo Ramos’ transfer, underline their market control. Even their missteps, like Hugo Ekitike’s £30 million signing and subsequent sale to Eintracht Frankfurt, turned profitable when PSG pocketed 20% of Frankfurt’s £69 million resale.

Chelsea, too, have turned sell-on clauses into an art form. While few academy graduates break into their first team, many thrive elsewhere with built-in clauses ensuring Chelsea continue to profit. Tino Livramento once said, “It’s probably the best academy in the world to develop in,” and hinted at a potential £50 million buy-back clause. Though Chelsea never exercised it, his £32 million move to Newcastle in 2023 earned the Blues around £20 million due to a sliding sell-on clause.

Barcelona’s financial meltdown following Neymar’s departure to PSG remains infamous. Their panic-buy spree – which included Ousmane Dembele, Philippe Coutinho, and others – proved disastrous. Liverpool famously benefited from Coutinho’s record sale, while Rennes profited handsomely from a clause in Dembele’s £13 million move to Borussia Dortmund, receiving around £17 million when Barcelona paid £135.5 million for him a year later. Rennes even issued a proud statement highlighting their role in developing a future Ballon d’Or contender.

Independiente del Valle’s honorary president, Michel Deller, called their Caicedo windfall “a ton of money for us,” after Brighton signed the midfielder for £4.5 million when Manchester United hesitated. The Ecuadorian club could never have imagined Chelsea’s eventual £115 million purchase following an intense tug-of-war with Liverpool – a move that redefined the modern transfer market.