10 Summer Transfers of the Past 10 Years Arsenal Fans Wish Had Not Happened

The summer transfer window is ostensibly an exciting time, but there are still moments of pain along the journey.

In this piece, we reflect on 10 transfer deals of the past decade that have given Arsenal fans some cause for regret. Join us as we count down through a list of deals Gunners supporters wish had never gone through.

10. Park Chu-Young to Arsenal

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Park Chu-Young was a relatively harmless addition to the Arsenal squad, given that he barely figured in a competitive game.

However, had he not joined, perhaps Arsene Wenger would have recruited a more competent striker. As it was, Park was simply a waste of money.

9. Sebastian Squillaci to Arsenal

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Sebastian Squillaci was so bad at Arsenal that he was almost a cult figure. Despite arriving with a reputation as a reliable central defender and regular France international, he never looked at home in the Premier League.

He is perhaps most commonly remembered for charging into his defensive partner, Laurent Koscielny, with such force that he nearly knocked him clean out.

Squillaci was a disastrous signing, and Arsenal fans were left feeling they would have been better off without him.

8. Mathieu Flamini to AC Milan

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In 2007/08, Mathieu Flamini grew from a mere understudy to an essential part of the Arsenal first team. However, at the end of the season, he left to join AC Milan on a Bosman transfer.

That was a massive blow to Arsenal, who thought they'd discovered a successor to Gilberto Silva at the base of their midfield. Although Flamini has since returned, he has never quite been the same player.

7. Mikael Silvestre to Arsenal

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When Arsenal signed Mikael Silvestre from Manchester United, he ought to have brought experience and authority to their defence. Instead, he largely brought chaos.

Silvestre played as if he were a secret agent deployed by Sir Alex Ferguson to ensure Arsenal could not mount a credible title challenge. The reality is he was simply over the hill. Arsenal supporters will wish Wenger had brought in a younger player without such strong ties to a rival club.

6. The Ashley Cole-William Gallas Swap Deal

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In the swap deal involving William Gallas and Ashley Cole, Arsenal definitely came off worse.

Cole went on to lift the Champions League with Chelsea, while Gallas was a disastrous captain at Arsenal. His post-match tantrum against Birmingham City in 2008 is still seen as the genesis of the Gunners' collapse in that season's title race.

Although it initially seemed like a fair exchange, time proved that Chelsea undoubtedly got the better end of the deal. Also, the loss of Cole was a big shame for Arsenal: Although the relationship soured, he was an academy product and ought to have remained in north London for his entire career.

5. Eden Hazard to Chelsea

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Arsene Wenger admitted to BeIN Sports (h/t the Daily Mail) that he had Eden Hazard's agent at the time, John Bico, around at his house but could not get the deal over the line.

What a blow, then, that he chose to join Chelsea, propelling Arsenal's London rivals to great success in the process. Had Arsenal found the funds to secure Hazard, the past few seasons might have turned out somewhat differently.

4. Thierry Henry to Barcelona

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Seeing a legend depart is always difficult, and Arsenal fans were understandably stung by Thierry Henry's move to Barcelona.

Although he later returned to the club on loan, Gunners fans would surely rather he had never gone away. This transfer was part of the steady flow of stars away from the Emirates Stadium that happened after the decision to leave Highbury.

3. Robin van Persie to Manchester United

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Losing your best player is always hard. Losing your captain? Even harder. Losing both to a hated rival and then watching him win the title in his first season there is horrific. Just ask Spurs, who went through the same thing when they lost Sol Campbell to Arsenal in 2001.

Robin van Persie's defection to Manchester United made Arsenal fans sick to their stomachs. His reputation in north London has been tarnished beyond repair.

2. Cesc Fabregas to Chelsea

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If seeing Cesc Fabregas leave for Barcelona was bad enough, seeing him return to join rivals Chelsea was arguably every bit as bad.

The pain was exacerbated by the fact that Arsenal declined to exercise their first-option clause on the midfielder. It was understandable the Gunners felt they didn't need another creative midfielder, but Cesc and the Arsenal fans shared a great bond, and it was traumatic to see him sign for Chelsea.

Seeing him turn out in blue remains a painful experience for Arsenal fans.

1. Cesc Fabregas to Barcelona

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This might be the most regretful transfer dealing of the past decade for Arsenal fans.

Cesc Fabregas was an idol at the Emirates Stadium but broke Gunners supporters' hearts when he decided to return to Barcelona.

The switch set Arsenal back some way and ultimately led to Fabregas returning to the Premier League with Chelsea. It was the most painful and pivotal transfer in Arsenal's recent history.