Dennis Wise (Newcastle)
Some of the transfer dealings done during Dennis Wise's tenure as 'executive director' were awful.
James Milner was sold to Aston Villa late on in the transfer window and no replacement could be found.
Added to sale of Milner were the awful signings of Xisco and Ignacio Gonzalez. The former cost £7 million, played 13 games and scored once.
Newcastle were relegated at the end of Wise's nine months in the role.