From Messi to Ronaldo: 10 deals Arsenal could have completed under Arsene Wenger

Arsenal's French coach Arsene Wenger crouches on the sideline during the UEFA Europa League semi-final second leg football match between Club Atletico de Madrid and Arsenal FC at the Wanda Metropolitano stadium in Madrid on May 3, 2018.. / AFP PHOTO / PIERRE-PHILIPPE MARCOU

If Arsene Wenger's Arsenal tenure can be summed up by anything, it's his track record of signing relatively obscure players and turning them into world-beaters.

There were players like Dennis Bergkamp and Patrick Vieira, both highly rated, but never at the level they reached under the Frenchman.

Thierry Henry was a struggling winger when he arrived at Arsenal, before turning into the most deadly striker in European football.

Then there are names like Cesc Fabregas, Emmaneul Adebayor, Kolo Toure - the list goes on an on.

During his 22-year spell at the club, Wenger won three Premier League titles as well as a staggering seven FA Cup winners' medals.

But it wasn't just the players that ultimately signed for Arsenal, that showed Wenger's foresight in the transfer marlet. There is a 'who's who' of generational talents that could have joined Wenger's revolution in North London.

Arsenal pulled off a major coup in the summer of 2003, signing Cesc Fabregas from Barcelona’s famed La Masia academy. But it could have been an even more memorable summer, with Fabregas’ teammate, Lionel Messi ‘tempted’ by a move to England.

Wenger admitted Arsenal were in talks with the diminutive Argentinian youngster, but he opted to stay in Spain – with former Gunners scout Francis Cagiago revealing work permit issues aso blocked the move.

“With Messi, work permit issues ensured we couldn’t get as close as we would have liked,” Cagiago explained. “And that’s all I can say on that. A lot get away - two, three, four a year - but I prefer to look at the ones we did get.”

Cristiano Ronaldo

Serie A - Juventus v Atalanta - Allianz Stadium, Turin, Italy - July 11, 2020 Juventus' Cristiano Ronaldo celebrates scoring their first goal [REUTERS/Massimo Pinca]

A front three of Ronaldo, Thierry Henry and Dennis Bergkamp anyone?

Well it almost came to be back in 2003, in-fact Wenger admitted that the Portuguese sensation even had the Arsenal shirt ready for a transfer.

“Maybe the closest was Cristiano Ronaldo, when he signed for Man United,” Wenger said earlier this week.

“We had an agreement with Sporting and Man United took Carlos Queiroz as assistant coach, and they just outbid us quickly and took Ronaldo. But we had an agreement basically.

“He had the shirt of Arsenal, I had lunch with him and his mother at the training ground!

Ultimately he would opt to join Man United...it seemed to work out, for everyone but Arsenal.

Gerard Pique

Similarly to his Barcelona teammates Messi and Fabregas, a young Pique was in talks over a move to north London in 2003.

Like the move for Messi, it broke down, with the central defender instead opting to join Manchester United.

It wouldn’t work out too well for him, returning to the Camp Nou in 2008, where he would go on to win every trophy available to him.

In a period where Arsenal struggled to recreate their miserly defence from the 90s, Pique is one that still hurts.

Juan Mata

Arsenal had two bites at the cherry to sign Juan Mata and failed on both occasion.

Firstly as a youngster, Cagiago revealed they were “very,very close” to signing the Spain international.

And then when Cesc Fabregas was leaving the club in 2011, Arsenal’s chief negotiator was sent to Spain to sort a deal for the then Valencia star.

“Juan definitely wanted to come to Arsenal, there was no question about that,” Law explained.

The Gunners would ultimately baulk at his £37m fee, leaving the door open for Chelsea to sign him.

Zlatan Ibrahimovic

AC Milan’s Zlatan Ibrahimovic celebrates after scoring scores his side’s first goal during the Serie A soccer match between Inter Milan and AC Milan at the San Siro Stadium, in Milan, Italy, Saturday, Oct. 17, 2020. (Spada/LaPresse via AP)

Another player who had the Arsenal shirt, only to not become an Arsenal player.

In fairness to Wenger, the precocious Ibrahimovic was right at the start of his career and it would be another three years before he truly burst onto the scene with Ajax.

A 17-year-old Zlatan had a trial with the Gunners before not signing, but it’s one decision that doesn’t keep Wenger up at night.

Asked if he had any regrets, he said: “Not really, because he was a 17-year-old boy playing at Malmo in the second league in Sweden. And nobody knew him. We gave trials to many players at 17 - it was absolutely normal before you make a decision.”

Yaya Toure

Since Patrick Vieira decided to end his illustrious spell with the club, every central midfielder signed since has been dubbed the “new Vieira”.

But two years before he left, Arsenal had the opportunity to sign a player that could have almost certainly filled the void.

Aged just 20, the Ivorian had a trial for the Gunners, even playing in a pre-season friendly.

Wenger revealed that the club had an agreement with the player, only for him to join Metalurh Donetsk instead.

N’Golo Kante

Premier League - Crystal Palace v Chelsea - Selhurst Park, London, Britain - December 30, 2018 Chelsea's N'Golo Kante in action [REUTERS/David Klein]

Another potential heir to the Vieira throne, Wenger admitted they failed to sign the Frenchman on two occasions, instead opting to bring in Granit Xhaka when Kante swapped Leicester for Chelsea.

Asked if he tried to sign him, Wenger said: “Yes. When he was in France, when he was at Leicester. Then again, I cannot explain everything but it's quite obvious when you look where he’s gone.”

Gianluigi Buffon

Before Buffon made the move to Juventus to become the world’s best goalkeeper, the Italian admitted that Arsenal made an approach to sign him.

The move came at the back end of David Seaman’s storied career with the club and little did Wenger know the struggles he would have to replace him.

In the years following Seaman’s exit, Jens Lehmann, Manuel Lamunia, Lukasz Fabianski, Vito Mannone, Wojchech Szcezsny and David Ospina were all tried before Petr Cech’s arrival in 2015.

Had they got a deal over the line for the young Buffon, it could have made that transition a lot smoother.

Vincent Kompany

Arsenal tried to sign the Belgian in 2006, while he was with Anderlecht, only for his agent Jacques Lichtenstein to advise his client against the move.

Lichtenstein said: “I had meetings with Emilio Butragueno at Real Madrid, the club leaders at Barcelona and by Arsene Wenger himself at Arsenal.

“But heading to an absolute top club immediately was not the right solution because Vincent is someone who feels alone in an environment where he is not properly valued. Vincent is not a third or fourth choice.”

Just two years later, he started an 11-year stay in the Premier League, winning the biggest prize on four different occasions.

Didier Drogba

Chelsea's Didier Drogba celebrates after scoring during their English Premier League soccer match against Manchester United at Old Trafford in Manchester, northern England October 26, 2014. [REUTERS/Phil Noble]

A real sliding doors moment for both Arsenal and Wenger. Back in the Ivorian’s youth, he had the chance to sign the striker for just £100,000, he opted against it at that point, only to be reminded of his mistake on a regular basis.

"I would have loved to have managed Didier Drogba, for two reasons," said Wenger.

"One, I missed him when he played at Le Mans in France, not even in the top league. I knew there was a good player there and I missed him.

"And secondly, because he hurt us so much in big games that all this pain would not have happened."

Drogba scored a staggering 13 times in 15 games against Arsenal – and it could have been oh so different.