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#3 Sale of Patrick Vieira to Juventus
Patrick Vieira was considered one of the best players of his generation and was among the best midfielders in the Premier League during his nine-year spell at Arsenal.
The Frenchman joined Arsenal in 1996 and became the club captain in 2002 following the retirement of Tony Adams.
Vieira famously led the Gunners to the historic 'Invincible' Premier League season in 2003-2004, in which the London club avoided defeat all season. But he was surprisingly sold to Juventus in 2005 after reports claimed Arsenal were ready to let him go.
The midfielder won ten trophies during his time in North London before moving to Italy, where he achieved more success.
It would remain bewildering why Arsenal opted to sell a player who was included in the Premier League Team of the Season on six consecutive occasions.
#2 Signing of Willian from Chelsea (Free)
Arsenal announced the signing of Willian on a free transfer from Chelsea earlier in the season. But it came as a surprise why Arsenal seemed to have inculcated the habit of signing ageing players from Chelsea.
Willian joined the likes of Peter Cech and David Luiz, who made the same move following their spell with the Blues.
The Brazilian spent seven seasons at Chelsea, and while he achieved moderate team success, individually, he was glaringly inadequate.
The winger never hit double figures in the league in all seven seasons at Stamford Bridge, scoring just 37 Premier League goals in 234 games for Chelsea.
Arsenal, who obviously needed more firepower coming into the season, oddly opted to sign an ageing player known for his unproductivity.
The winger has gone on to make 30 appearances for the Gunners this season but still awaits his first goal for the club.
#1 Alexis Sanchez - Henrikh Mkhitaryan (swap deal)
Perhaps the most bizarre swap deal in recent Arsenal history, Alexis Sanchez moved to Manchester United from Arsenal while Henrikh Mkhitaryan headed the other way. But it turned out to be a move that somehow failed to work out for either the clubs or the players.
The move ultimately turned out to be a horror show for both players, as Sanchez scored an abysmal five goals in 45 games for the Manchester side, while the Armenian netted just nine in 59 games for Arsenal.
Both players subsequently moved on to Italy, with Sanchez going to Inter Milan, and Mkhitaryan moving to AS Roma. Both cases were initial loan deals that were later made permanent.
Fortunately for the two players, their moves away from the Premier League have helped them regain their mojo as both men are now key players for their respective clubs.
