During the first half of Arsene Wenger’s 22-year reign as Arsenal manager, it was almost unheard of for the club to be selling players for big money. Just three high-profile players left Highbury for fees over £13,500,000 before Thierry Henry exited the Emirates for Barcelona in June 2007.
That isn’t to say that the Gunners didn’t get rid of players during the early Wenger years. Nicolas Anelka, nicknamed Le Sulk by the tabloids, was the first big money outward transfer of the iconic manager’s reign when he left for Real Madrid in August 1999, sold for 45 times the outlay.
Dutch winger Marc Overmars moved to Barcelona for a reported £25,000,000 the following summer, a record fee received by Arsenal that would stand for over a decade. The injury-prone Netherlands wideman generated a fourfold profit on how much he cost to bring in from Ajax three years earlier.
Wenger and the Gunners resisted selling anyone for a sizeable fee for five years after Overmars. Club captain and influential midfielder Patrick Vieira departed for Italian Serie A giants Juventus in the summer of 2005. Henry then followed in Overmars’ footsteps by joining Barca for £16,000,000.
What is notable about the high-profile departures during the first half of the Wenger years is Arsenal sold to overseas clubs and not to domestic rivals. That all changed in July 2009, however, when Manchester City splashed out around £40,000,000 to take both Togo striker Emmanuel Adebayor and Ivory Coast defender Kolo Toure north to the Etihad.
Barcelona still brought in Gunners to the Nou Camp, with Cesc Fabregas setting a new record fee received in August 2011 then fellow midfielder Alex Song following for half the price 12 months on. Belgium defender Thomas Vermaelen also moved from North London to Catalonia for an initial £15,000,000 over the summer of 2014.
While Samir Nasri followed Adebayor and Toure to City in 2011, selling players Manchester United would’ve been unthinkable at the height of the touchline rivalry between Wenger and Sir Alex Ferguson. Nonetheless, in August 2012, Netherlands striker Robin van Persie left the Emirates for Old Trafford for £22,500,000 up front and Arsenal fans had to watch him fire the Red Devils to the Premier League title.
Humbling as that was, the Gunners would get the better of a high-profile swap deal involving United during the infamous winter window of 2018. Armenia winger Henrikh Mkhitaryan moved south and Chile forward Alexis Sanchez, one of the greatest Premier League transfer flops ever, went the other way. So prolific in an Arsenal shirt, the South American star simply didn’t do the business for United.
In January 2018, there was a real changing of the guard for the Gunners in attack. Not only did Sanchez leave the Emirates but Theo Walcott went to Everton in a £20,000,000 deal and France striker Olivier Giroud moved across London to Chelsea, where he has since lifted the FA Cup, Europa League and Champions League.
Arsenal’s biggest sales have been to clubs on Merseyside. Nigeria’s Alex Iwobi followed Walcott to Goodison Park in August 2019, but two years earlier the record fee received was set by Liverpool brokering a deal potentially worth £40,000,000 including add-ons for Alex Oxlade-Chamberlain. His record with injuries meant the offer for the England midfielder was too good to turn down. The Gunners’ last major sale was the £20,000,000 transfer of Argentina goalkeeper Emiliano Martinez to Aston Villa during September 2020.
