Arsene Wenger achieved many special things in his career. At Arsenal, he changed the face of English football as he delivered three Premier League titles and seven FA Cups.
One of his best talents was picking up undervalued talent and transforming it into elite footballers. Club icons such as Patrick Vieira, Kolo Toure, and Nicolas Anelka all spring to mind on that front.
One name, however, stands above the rest. Indeed, Thierry Henry is synonymous with Wenger's time in north London as the pair conquered English football together, most famously in 2003/04 during the Invincibles season.
Despite all of his success, the French manager has since admitted that he holds some 'big regrets' about his tenure with the Gunners. Highest on that list, he revealed in 2018, was the failure to sign one Premier League legend to play alongside Henry.
Wenger Wanted Cristiano Ronaldo at Arsenal
Dreamt of having him alongside Thierry Henry
With his talent ID so good, Wenger missed out on many great signings over the years. Indeed, he had his eye on the likes of Raphael Varane, Kylian Mbappe and Yaya Toure when they were all young.
That said, there is one footballer who may well have changed the trajectory of Arsenal had he arrived at Highbury in the early 2000s. That man is Cristiano Ronaldo. Wenger explained:
"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 at the time, who was their coach. 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... That would certainly have changed a little bit the history of my stay here as well."
Cristiano Ronaldo's Record vs Arsenal
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Wenger Explained Arsenal Did Not Sign Ronaldo
"We were very close"
Arsenal's lack of finances during Wenger's reign where often to blame when they missed out on key signings. Once more, this cost them when they were pipped to Ronaldo by rivals Manchester United. The Frenchman explained:
"There is always something you could have done differently, but the problem of negotiations is to know when you give in and when you don't give in.
"Once we were at 4.5 million pounds, we were still in negotiations... so we were very close. But Man United went to 12 million pounds, which we could not afford at the time."
Between them, Henry and Ronaldo scored 278 Premier League goals, won five league titles, and are among the very best to have ever played in the English top flight. Had the five-time Ballon d'Or winner joined, it would have changed the trajectory of football, with Arsenal significantly strengthened and their bitter rivals Man United severely weakened.
One can only imagine what could have been.
Stats via Transfermarkt