Left Winger: Cristiano Ronaldo
In an alternate universe, one where Sir Alex Ferguson did not exist, Wenger may have signed Cristiano Ronaldo and won trophies by the dozen. Instead, he lost out on the Portuguese winger in 2003 as the Scottish manager stepped in and worked his magic to bring the highly-rated youngster to Old Trafford.
“My biggest regret: I was so close to signing Cristiano Ronaldo. And not only did I not get him, but he signed for Manchester United. That, of course, still hurts today.” – Wenger in 2014
Ronaldo only need show the trophies he has won ever since to prove how terribly wrong Wenger was to not sign him up quickly. Four league titles, three Champions League trophies, four Ballons d’Or, numerous goalscoring records... Ok, we’ll give Wenger a break at this point.