2. Cristiano Ronaldo (Arsenal and Liverpool)
Arsene Wenger stated that missing out on Cristiano Ronaldo in 2003 was his biggest transfer regret at Arsenal. The Gunners were reportedly the first to be attracted by the talented then Sporting Lisbon player and invited him to their training center at the age of 15. However, the deal fell through due to the fact Arsenal did not have the funds to meet the asking price.
A few months later, Manchester United secured the services of the player. “My biggest regret? I was so close to signing Cristiano Ronaldo, and not only did I not get him, he signed for Manchester United. So that of course still hurts today,” Wenger revealed during an interview in 2014.
The Gunners were not the only English club that snubbed the Portuguese. Liverpool were the pioneers. Gerard Houllier, who managed the club from 1998 to 2004, admitted that he saw Ronaldo during an Under 21 tournament in 2003, some negotiations took place but the deal ultimately fell through due to wage demands.
1. Zlatan Ibrahimovic (Arsenal)
Oh boy – Another of the many Arsenal snubs. They snubbed him by putting him on a trial, so he snubbed them – classic Ibra. The Swedish ace felt insulted by Arsene Wenger’s insistence he “audition”, so he moved to Ajax instead. After signing for the Dutch giants in 2001, Zlatan revealed: “I’d like to show them what they missed.”
Back to the present day and Ibrahimovic has not forgotten famously posing with the Arsenal No9 jersey 16 years ago. He told Sky Italia: “I went to London for an appointment with Wenger, who asked me to audition for the Gunners “I told him ‘I will not do a trial: either you take me or not, I’m not here to waste time’.
“I already had that kind of trust, because in my mind I was the strongest of all even when I was young. I met Wenger because I expected him to tell me to start with them right away. But Ibra does not test. When I was young, in my mind no one was better than me”, he ended.
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