Arsenal’s 10 biggest transfer sale mistakes

Nicholas Hughes
Vieira confirms Daniel Ek will keep attempting to buy Arsenal from Stan Kroenke

Arsenal have been a household name in European football for some time, being one of the continents true powerhouses at the beginning of the 21st century.

With the territory comes some of the world’s best players, and Arsenal have had some stellar names lining up at Highbury and at Emirates Stadium over the years.

While the Gunners have historically not been the most willing of spenders in the transfer market, there have been plenty of deals involving some top players, and the club haven’t always got it right.

Sales of top players have been transacted, and mistakes have been made along the way. Here is a list of the 10 biggest transfer sale mistakes that Arsenal have made.

Emiliano Martinez – Aston Villa, 2020 (£17m)

Emiliano Martinez was afforded a first-team opportunity in 2020 when Bernd Leno suffered an injury after the Premier League’s return from the COVID-19 shutdown.

The Argentine was outstanding to close the season for the Gunners and was instrumental in Mikel Arteta’s side claiming a famous FA Cup final victory, as well as the Community Shield soon after.

It came as a big surprise when he was allowed to leave for Aston Villa a matter of weeks after that Community Shield success, and for a quite minimal fee of around £15.6 million.

The signing of Aaron Ramsdale for almost double what they recouped for Martinez makes the sale all the more curious, and particularly given Martinez’s outstanding debut season at Villa Park.

Alexis Sanchez was a great goal scorer for Arsenal

Alexis Sanchez was a great goal scorer for Arsenal

Alexis Sanchez – Manchester United, 2018 (swap for Henrikh Mkhitaryan)

Alexis Sanchez was near untouchable at times for Arsenal. Joining from Barcelona in 2014, the Chilean was brilliant to watch on the left wing and had Arsenal as close to a league title as they had been in some time.

But the issues of old remained, and Sanchez saw a chance to move on in search of what he thought was a greater likelihood of success.

As it turned out, Sanchez’s stint at Manchester United was underwhelming at best, but Henrikh Mkhitaryan was nowhere near matching Sanchez’s levels when he came across the other way in the move.

Letting Sanchez go to Man Utd was a critical mistake, it pushed Arsene Wenger closer to the trap door and Arsenal have not been the same team since he left.

Serge Gnabry – Werder Bremen, 2016 (£4.5m)

Hindsight would not have seen Serge Gnabry quite developing the way he has done, but this sale is a monumental error from Arsenal’s point of view.

Gnabry was hardly given a chance at Arsenal, playing just 10 times in the Premier League before a loan spell at West Bromwich Albion.

The Gunners sold Gnabry to Werder Bremen in 2016 for a measly £4.5m, and after scoring 11 Bundesliga goals, he moved on to Bayern Munich just 12 months later.

He has gone on to become a Champions League winner, three-times Bundesliga champion and a staple in the German national team, leaving Arsenal red faced over his premature sale.

Van Persie left Arsenal in pursuit of silverware

Van Persie left Arsenal in pursuit of silverware

Robin van Persie – Manchester United, 2012 (£24m)

While this was a sale that Arsenal did not want to have to make, Robin van Persie made it very clear in the summer of 2012 that he wanted out in order to challenge for a league title.

Much to the fury of the Gunners faithful, van Persie made the switch to Sir Alex Ferguson’s Manchester United, and sure enough he had a Premier League winner’s medal around his neck to show for it.

While Arsenal replaced RVP with Olivier Giroud, who proved a successful signing of not spectacular, the Gunners have struggled to recover since seeing their captain walk out the doors.

Samir Nasri – Manchester City, 2011 (£25m)

Samir Nasri emerged as one of the league’s best players at Arsenal, but as was becoming a trend for the Gunners at the time, the Frenchman saw titles elsewhere.

Pushing for a move in the summer of 2011, Arsenal were forced to sell Nasri to Manchester City for around £25m, and once again, he won the Premier League after just one season away.

Arsenal lost left-back Gael Clichy to City in the same window, another example of the club strengthening Premier League rivals due to their limited chance of winning silverware.

Another sale that was perhaps out of the club’s control, but one that has gone down as a big mistake nonetheless.

Fabregas was one of Arsenal's most gifted players

Fabregas was one of Arsenal's most gifted players

Cesc Fabregas – Barcelona, 2011 (£30m)

The summer of 2011 was a painful transfer window for Arsenal, and the one that hurt the most was the loss of their captain and star midfielder as Cesc Fabregas returned home to Barcelona.

This sale marked the first of the sales already mentioned that saw star players leaving for better opportunities elsewhere, and all for relatively low sums of money.

Fabregas was integral to Wenger’s side and any chance they had of winning trophies, and allowing him to leave so easily was one of the biggest transfer blunders in the club’s history.

Adding insult to injury, Fabregas would return to the Premier League just three years later and played a starring role for bitter rivals Chelsea, winning two Premier League titles with the Blues.

Thierry Henry – Barcelona, 2007 (£16m)

Still arguably the Premier League’s greatest-ever player, Thierry Henry was allowed to move to Barcelona in 2007 in a huge mistake from Arsenal.

Henry had given Arsenal two Premier League titles and taken them to the cusp of the Champions League, but a move to Barcelona was unavoidable as he chased the next step in his career.

The Frenchman won two La Liga titles and the coveted Champions League to justify the move on his part, but Arsenal’s transaction of the sale was a major mistake.

Ashley Cole left Arsenal in pursuit of trophies at Chelsea

Ashley Cole left Arsenal in pursuit of trophies at Chelsea

Ashley Cole – Chelsea, 2006 (£5m plus William Gallas)

Arsenal fans never really forgave Ashley Cole for pushing for a move to Chelsea, as the left-back jumped ship to the Gunners’ great rival.

The minimal transfer fee and the exchange of a player four years Cole’s senior made the deal all the more errant, with Gallas never really recapturing his best from while at the Emirates.

Cole went on to win one more league title with the Blues and lifted the Champions League in 2012, and the topic of his sale continues to be a touchy one for Arsenal fans.

Patrick Vieira – Juventus, 2005 (£18m)

This sale might be the most bizarre on the list. At 29 years of age, Patrick Vieira was still competing at a high level, having made the PFA Team of the Year every year from 1999 to 2004.

But the Frenchman was curiously allowed to join Juventus in 2005 and was replaced only by a very young Alex Song in what proved to be a massive mistake from Arsenal.

Vieira did only last a year at the Old Lady, but that was because he upgraded to Inter where he went on to win four Serie A titles in a row as well as a Champions League title in 2010.

Arsenal spent years trying to replace Vieira

Arsenal spent years trying to replace Vieira

Andy Cole – Bristol City, 1992 (£1.35m)

Possibly the most bizarre sale on the list, Arsenal let a 20-year-old Andy Cole leave their ranks in 1992 without so much as a single Premier League appearance.

Cole was sold to Bristol City for £1.35m before leaving for Newcastle United the following year, where he netted a stunning 34 goals in his first season of Premier League football.

Cole would of course go on to score 187 goals in the English top flight, holding the second-best record all-time for many years before he was overtaken by Wayne Rooney.

Continuing the trend of players winning trophies away from Arsenal, Cole lifted the Premier League five times and won the Champions League with Manchester United.