Francis Jeffers – £8m – 2001
Wenger admitted that he signed the Everton forward ahead of Ruud van Nistelrooy. While the Dutchman went on to have an illustrious career at Manchester United, Jeffers failed to make an impact at Highbury.
He scored just eight goals during three years with the Gunners. He struggled with form and fitness issues before being sold at a significant loss to Charlton.
