#1 Gonzalo Higuain (Signed for £75.3m): Juventus to AC Milan
Back in 2015/16, Gonzalo Higuain nearly made history when he finished as Serie A's top goalscorer with 36 goals for Napoli. It was a record-equalling feat, achieved by Gino Rossetti of Torino - 87 years prior!
The Capocannoniere then sealed a record-breaking move to Juventus who were hungry for more success after dominating the Italian top flight. With an eye on the Champions League, Higuain tried to make it work but he didn't hit the same heights despite scoring 32 and 23 goals in his two seasons with The Old Lady.
That was when Juventus decided to make good on their long-term vision of signing a superstar like Cristiano Ronaldo. Years ago, they had said they would sign a player like him and eventually settled for Ronaldo himself.
But spending £99.2m on the transfer and a further eye-watering €30m a season on his wages, they needed to offload a big player to balance the books.
That is where Higuain, sadly, became the sacrificial lamb to be sent on loan to AC Milan. There was no way they were going to sell Paulo Dybala while Mario Mandzukic would certainly not have fetched enough.
Higuain was used as a pawn to ensure Juventus would also get Leonardo Bonucci back from Milan with Juve's Mattia Caldara also making the switch to the Rossoneri.
Milan signed Higuain for a loan fee of £16m and also have the option of making his move permanent for a transfer fee in the region of £32m.