#1 Lionel Messi (Age: 16)
The only spurned signing that hurts more than Ronaldo is Lionel Messi. In 2003, Wenger tried to sign a promising trio from Barcelona’s La Masia. Thinking that he wouldn’t see much time in Catalonia, Cesc made the difficult decision to leave home and head for England.
Gerard Pique and the precocious Lionel Messi, however, found Barcelona too cosy to leave at such a young age.
Some within the media will tell you that Arsenal’s failure to find a home for Messi’s family led to the failure of the deal.
But Wenger believes that Messi simply had finally made himself comfortable in a foreign country and wasn’t ready to uproot himself so soon after settling in Spain.
Had Messi pledged his allegiance to Arsenal at 16 and showed the same commitment he’s shown Barcelona, Wenger wouldn’t currently be having a three-quarters life existential crisis.