Marc Overmars
© Offside
This was an example of Wenger putting his trust in a clearly talented individual, as Marc Overmars had suffered injury problems with Ajax prior to joining Arsenal for £5.5m in 1997.
The Dutch winger required little time to leave a mark, scoring the opening goal in the FA Cup final en route to lifting a league and cup double in his maiden campaign at the club.
Overmars gave his best years to Arsenal, failing to light up Barcelona in quite the same way when making a £25m switch in 2000 - a mammoth profit on a player who would announce his retirement four years later due to a persistent knee injury.