This month marks 20 years since Arsene Wenger missed out on bringing Cristiano Ronaldo to Arsenal.
The Portuguese star went on to sign for Manchester United six months later and well, the rest is history. But just how close did the Gunners come to bringing Ronaldo to Highbury?
At the age of 17, he broke through Sporting Lisbon’s academy and into the first team, making his debut in the Primeira Liga in September 2002.
And it took just two months for then-Arsenal manager Wenger – who led the Gunners to three Premier League titles and seven FA Cups amongst other accolades – to notice him.
The Frenchman built up a long list of missed transfer targets during his management career, but none more famous than Ronaldo, who describes as his ‘biggest regret’.
The Gunners were in talks with then-teenage Ronaldo while he was still in Portugal with a view to get him to make the permanent switch to north London.
Wenger even met the emerging talent at Arsenal – the then-reigning Premier League champions – in November of that year and introduced him to his coaching staff.
And according to journalist Guillem Balague, Ronaldo’s agent Jorge Mendes has confirmed the Gunners nearly signed his star that January.
However, with the construction of the Emirates in the works, the club were short on funds and it wasn’t possible to make the move happen.
Fast forward to August, and less than a week after Ronaldo impressed Sir Alex Ferguson in a pre-season friendly against Man United, he was a Red Devils player, signing for £12million.
During his years at Old Trafford, Ronaldo won the first of his five Ballon d’Ors thanks to his ludicrous goal tally of 42 in 49 appearances in the 2007/08 campaign, as well as being a key player in the Man United sides that dominated English football in the 2000s.
And Ronaldo himself has previously revealed just how close he was to signing for Arsenal, instead.
In an ITV interview with Piers Morgan in 2019, he revealed: “It’s true. Very close. One stop, incredible. Seriously. It didn’t happen but, Arsenal, I appreciate what they did for me.
“Especially Arsene Wenger – but you know football and in football you never know.”
And Wenger has admitted missing out on Ronaldo is a source of frustration.
Speaking in 2014, Wenger said: “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.”
Before Ronaldo’s then-world record £80million move to Real Madrid in 2008, Wenger was forced to watch on in envy as his former target netted 118 times for Man United.
The end of Ronaldo’s second spell at Old Trafford certainly left a sour taste in the mouths of those that have spent the last two decades seeing him as a Man United icon.
The star recently completed a £177-million-per-year move to Saudi Arabian side Al-Nassr after his explosive TalkTV interview with pal, Morgan, which saw him have his Man United contract mutually terminated.
But who knows what route the 37-year-old’s career could’ve taken had he ended up playing in Gunners red over Man United’s two decades ago.
Ronaldo playing in the ‘Invincibles’ with Thierry Henry, Robert Pires and Dennis Bergkamp? Oh what could have been.