Arsenal have had some world-class midfielders over the years, but also missed out on signing some of the best in the position.
In 2008, Arsenal narrowly missed out on the Premier League title, but were blessed with a top-quality midfield.
The quartet of Cesc Fabregas, Mathieu Flamini, Alexander Hleb and Tomas Rosicky was capable of dismantling teams whilst playing some of the most fluid and attractive football of Arsene Wenger’s reign.
However, this could have been upgraded to a title-winning midfield with one more addition. For years, Arsenal lamented the loss of Patrick Vieira, and only now with Declan Rice has his presence in midfield been replaced.
Arsenal could have signed a truly world-class defensive midfielder in Xabi Alonso, and whilst he was of a different mould to Vieira, he could have formed a midfield alongside Fabregas and Hleb which could have become one of the best rosters in the world, and Wenger was remarkably close to securing his signature.

Rafa Benitez reveals Arsenal agreement to sign Xabi Alonso in 2008
Speaking on the Stick To Football Podcast, former Liverpool manager Rafa Benitez revealed that Arsenal had an agreement to sign Alonso during his time on Merseyside, but the move was blocked as he needed to play in a Champions League qualifier.
“When we went for Gareth Barry, it was because he could play in three different positions and then we needed to sell. Xabi had an agreement; he was talking with one club and had an agreement,” Benitez stated.
“The year after, we played Standard de Liege for a Champions League qualifier and we had Javier Mascherano and Lucas Leiva in the Olympic Games, Steven Gerrard had a lower back problem, so we had to play [Damien] Plessis and Xabi.
Xabi had an agreement with Arsenal and didn’t want to get cup-tied.
“I told Jamie Carragher and Gerrard before the game that he had an agreement, and doesn’t want to play, but he must because it is the most important game to qualify for the Champions League.
“Then when you were going out for the warm-ups, you [Carragher] said, ‘Poor Xabi.’ Not poor Xabi, he is playing for our club at this time. During the season he was our best player and didn’t go to Arsenal because he had to play [for us].”
Xabi Alonso could have had huge knock-on effect for Arsenal
The domino effect of Alonso’s failed move to Arsenal was massive. If he had joined, and potentially won a league title, then stars such as Fabregas and Robin van Persie may not have pushed for moves.
Liverpool won the qualifier against Standard Liege, and Alonso stayed at the club. Liverpool would reach the quarter-finals of the Champions League, whilst Arsenal reached the semis in that season, and both teams lost to the eventual finalists Chelsea and Manchester United.
Arsenal finished 14 points behind Liverpool, but this gap could have been shortened if Alonso had moved.
Flamini departed Arsenal, and Alonso would have replaced and upgraded him. In the long-run, this may have meant that the Spaniard never played for Real Madrid, and this would likely have meant that Mikel Arteta never joined Arsenal, before eventually becoming manager.
This one deal therefore had a huge impact by falling through, and we may have seen a very different Arsenal side over the years and now had the move happened.
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