It was the summer of 2008. Spurs had already sold Robbie Keane to Liverpool and were preparing to lose Dimitar Berbatov to the vultures from Old Trafford.
With Berbatov already mentally checked-out, Darren Bent was the last striker standing and Spurs were scouting Europe trying to recruit a top class reinforcement.
One target was Diego Milito, then at Real Zaragoza, but he pied Spurs to return to former club Genoa.
Genoa football director Stefano Capozucca recently revealed this to Tutto Mercato Web. He said: “To return to Genoa he refused Tottenham, with us he made an extraordinary championship and landed at Inter.
“A particular purchase, but he was the most important player I have ever had.”
As Capozucca eludes to, Milito left Genoa a year later to join Inter Milan, with whom he won the Champions League in 2010 – scoring twice in the final.
After failing to land Milito, Spurs signed Roman Pavlyuchenko in August 2008. Keane then returned in the winter, as did Jermain Defoe from Portsmouth.
Milito left Inter in 2014 and ended his career in Buenos Aires with Racing Club.
He wanted to win something in his career.