The 5 worst signings in Real Madrid's history

1. Antonio Cassano

Antonio Cassano's time at Real was an unmitigated disaster

Italian striker Antonio Cassano lasted slightly longer at Real Madrid than Nicolas Anelka, but it’s safe to say that his tenure at the Bernabeu was even more chaotic and disastrous than that of the Frenchman. The second Italian player to sign with Los Blancos, hopes were high for Cassano after he’d shown flashes of his tremendous talent with Roma, although disciplinary issues at the club should’ve raised a red flag.

The €5m fee Real paid for the Italian seemed like a bargain at the time, but evidently the club didn’t know what they’d gotten themselves in for. Cassano did score a goal on his debut for his new side in a Copa del Rey match with Real Betis, but weeks later it became clear that he was hardly in a fit state to play football; his weight ballooned and Real began to fine him for every gram he remained over his optimum weight.

His first season ended with him scoring just 2 goals in 17 games, but worse was still to come. Cassano started the 2006/07 season badly and was then suspended for disrespecting the club’s new coach, fellow Italian Fabio Capello. From there he seemed determined to leave the Bernabeu, and it came as no surprise when the striker moved to Sampdoria on loan at the start of 2007/08, after a return of just 2 goals in 12 appearances for Madrid.

Years later, Cassano revealed that while at Real, he would eat “three or four” croissants a night – and also claimed to have bedded over 600 women during his time at the club. It was also revealed that he’d labelled Capello “faker than Monopoly money” in their clash. Both stories go a long way to explaining why he’s the worst signing in Real Madrid’s history.