#4. Francesco Coco – Clarence Seedorf (Inter Milan and AC Milan)
The ill-fated Francesco Coco-Clare Seedorf swap deal stands out as a perplexing move in football history. Inter Milan’s decision to trade the accomplished Seedorf, a four-time Champions League winner, for the relatively obscure Coco left fans scratching their heads. Seedorf’s stellar career at AC Milan, including Serie A titles and European triumphs, made the swap even more baffling.
In contrast, Coco, once touted as Paolo Maldini’s successor, failed to fulfil expectations and experienced a forgettable stint at Inter. His subsequent retirement at 30 and Hollywood aspirations marked a stark decline, highlighting the dubious nature of a trade that left Inter with little to gain and much to regret.