3) Guido Carrillo (Monaco to Southampton – £19.1m – 2018)
The Saints had money available after selling Virgil van Dijk to Liverpool for £75m, and manager Mauricio Pellegrino wanted a forward to improve their goal return.
He opted for a player he knew after working with Carillo back in his native Argentina. Despite having a mediocre record with Monaco, the club trusted their manager by shelling out almost £20m on the striker. It was a massive mistake. He played just five times before Pellegrino was sacked, with new manager Mark Hughes selecting him twice before loaning him out to Leganes. He eventually left on a free transfer for Elche in October 2020.
