Arsene Wenger was relatively unknown when he left Nagoya Grampus in Japan. The Frenchman made his way to Highbury to replace the iconic George Graham, who had been dismissed for financial misconduct.
Both Stewart Houston and Bruce Rioch were unsuccessful in holding managerial reins for long. Arsenal chairman Peter Hill-Wood turned to the Frenchman in September 1996 to steer the ship.
Wenger, who had also managed Monaco, was quick to make an impact with the Gunners. He soon transformed an Arsenal side known for its lethargic style of football and defending 1-nil leads into a dynamic unit that was among the most exciting to watch in Europe.
Missing out on Cristiano Ronaldo and other top targets
To play the way he did, Wenger had to attract the best talent. In his early years, he brought in many top names. Players such as Thierry Henry, Patrick Vieira, Lauren, Kolo Toure, Denis Bergkamp, Freddie Ljungberg, Emmanuel Petit, and Marc Overmars. That included Nicolas Anelka, who was Wenger's first signing in 1996.
Seven years later, Wenger achieved the unthinkable by lifting the 2003-2004 Premier League trophy while going all season unbeaten. It is a feat that has not been replicated since.
However, during the Frenchman's tenure, there were also many famous names that came close to joining Arsenal only for them to slip through their hands.
Cristiano Ronaldo, N'Golo Kante, Lionel Messi, Luis Suarez, Ibrahimovic and more recently, Kylian Mbappe were all at once linked to make the move to North London only for the deal to fall through at the last minute.
Such close misses have often been attributed to the Frenchman's lack of urgency in the transfer market.
The FIFA executive recently expressed how much he regrets his languid approach. But one name sits atop the list of Arsenal's would-have-beens.
Wenger shares his deepest regret
In a sit-down with former Arsenal striker, Ian wright, on Sportbible’s YouTube channel, Wenger addressed the issue once more.
It was during the course of the invisible season that Wenger had a chance to sign a soon-to-be world-beater for Arsenal.
The then 18-year-old Ronaldo was being eyed by the top teams in Europe. He visited both Highbury and Carrington, but it was Wenger's nemesis, Sir Alex Ferguson, who eventually got the coveted teenager.
Ferguson later admitted that it was United's players who had urged him to sign the Portuguese international.
They were on the receiving end of Ronaldo's impressive repertoire of talent when the young forward ran all over the likes of Rio Fedinard and John O'Shea in a pre-season friendly with Sporting Lisbon.
As a result, they wanted Ronaldo at Old Trafford.
While answering fans' questions to promote his biography "Arsène Wenger – Invincible", Ian read out a question seeking to know which player Wenger regrets not signing the most. Wenger responded by saying:
“Certainly Cristiano Ronaldo. I thought it was possible. And if we had been a fraction quicker…a few days because we had agreed and Man United came in 5-6 days later. I would say at the start of my career; Cristiano Ronaldo. At the end of my career; N’Golo Kanté.”
It's seemingly a regret that creeps up to haunt the legendary former Arsenal boss every now and then because this is the umpteenth time he's opened up about his closest transfer misses.
Wenger has been agonising over Ronaldo's botched transfer for the longest time
In 2018 while speaking to Arsenal.com in a fan Q&A session Wenger said:
“The obvious player [that we missed out on] that comes to mind is [Cristiano] Ronaldo. He was here with his mother and we were very close. Then Man United came in and they had Carlos Queiroz, who was their coach at the time. United played against Sporting Lisbon and Ronaldo was outstanding and they signed him. You could imagine at the time what it would have been like to have Thierry Henry and Ronaldo together. Later Man United had Rooney, Ronaldo and Van Nistelrooy together, they had an exceptional football team, and Giggs and Scholes together. That would certainly have changed a little bit the history of my stay here as well.”
Four years earlier he had also shared his grief in another Arsenal interview.
Wenger told Huawei, Arsenal's official smartphone sponsor at the time:
"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,"
Cristiano Ronaldo was one of many players who slipped through the hands of Arsene Wenger and Arsenal and went on to flourish at other clubs.