#1 Keirrison (From Palmeiras, €14m, 2009)
In the summer of 2009, Barcelona raised several eyebrows when they completed the signing of Keirrison from Palmeiras on a five-year deal that was initially worth €14 million.
It turned out to be one of the worst deals in football history as the Brazilian failed to make a single appearance for the Catalan giants.
Following his transfer to the Camp Nou, Keirrison was immediately loaned out to Portuguese giants Benfica. He was later sent out on loan four more times to clubs like Fiorentina, Santos, Cruzeiro, and Coritiba.
The forward, who permanently left Barcelona for Coritiba in 2014, never really managed to settle at any club and was last seen turning out for Brazilian Serie B outfit Londrina in 2018, aged 30.
What made Barcelona's then-manager Pep Guardiola sign Keirrison will forever remain a mystery as the player simply didn’t have it in him to make a mark at such a top European club.