Will the Gunners one day wish they'd kept hold of the England Under-21 striker?
Arsenal's decision to sell Benik Afobe to Wolves in January may be a decision Arsene Wenger comes to regret, with the reemergence of Francis Coquelin more than proving that a player can take his chance way into his 20s.
The young striker was long held up as an outstanding prospect at Arsenal, and proved this year that he has the quality to be a regular goalscorer as he first of all starred on a loan spell at MK Dons, scoring 19 goals in 30 games, before stepping up a division with ease as he was sold to Wolverhampton Wanderers.
The 22-year-old has fired Wolves into the playoff picture with his 8 goals in 14 games since arriving at Molineux.
But Arsenal fans should look at the pretty impressive ability Wenger has of knowing whether to let youngsters go or not as a good sign that the striker may not be quite good enough for the Gunners.
The former Monaco boss has often proved himself to have the midas touch when it comes to transfer decisions, particularly when recruiting and selling youngsters, though he may also have a few regrets regarding players that went on to prove themselves in some capacity.
So with Arsenal fans hoping that Afobe won't be one that the club hoped they'd held onto, here are five other Arsenal exits Wenger may just have wished had hung around a little longer:
Matthew Upson - Was sold to Birmingham for just over £1 million in 2003, and went on to prove himself a thoroughly capable Premier League defender over the years on the way to earning 21 England caps. Seeing as though Arsenal went unbeaten the season after, it's a somewhat excusable decision - at least until you see that Pascal Cygan was in that Gunners squad.
Steve Sidwell - Another player who proved himself to be a fine Premier League performer, Sidwell earned a high profile move to Chelsea after impressing at Reading following his release by Arsenal. Would likely never have become a first teamer, but could have been a decent squad player under Wenger.
Sebastien Larsson - A versatile player who never really convinced Wenger, despite getting a couple of opportunities as a youngster. Larsson impressed as soon as he went on loan to Birmingham, and has proved himself to be one of the league's best set-piece takers over the years.
Lassana Diarra - The feisty central midfielder wasn't prepared to bide his time at Arsenal, and in 2008, asked to leave in order to get regular first team football. The Frenchman had proved himself a promising option in the middle of the park, but much like Paul Pogba did at Manchester United, thought he was deserving of more time on the field. Diarra spent a season at Portsmouth before a transfer to Real Madrid, and though Wenger has since said he didn't regret letting the former Chelsea player leave, he must be conscious that Diarra could have been the defensive midfield answer his side needed for so long.
David Bentley - A controversial pick considering the way his career has gone in the last few seasons, but there can be no denying that at one point Bentley looked like one of the more talented footballers England had coming through. Left Arsenal for a reported £1.5 million in 2006, and starred at Blackburn Rovers before gaining England caps and earning a big money return to North London with Spurs. Things started to go downhill for the winger from there, and he is now retired from the sport citing a loss of interest in the game. But Wenger would surely liked to have taken the 30-year-old on a different career path had he have remained under his tutelage.