Tying a player to a club for another couple of seasons has to be a difficult job. Just ask Arsenal. Arsenal is known for letting go of players for a bargain or even for free! A player’s value is much less when he is on the last year of his contract compared to when he has a few years left.
Most teams have a tendency to let their players’ contracts go to the last year and then they try to offer them a contract. Some players end up rejecting the offer because it didn’t meet their needs or some accept it if they are satisfied. However, with Arsenal, the story is that they end up offering either too less or too much or sometimes they do not even offer a contract extension until it’s too late.
Some of the finest examples, of this club letting go of World Class players on a free or a bargain, are Aaron Ramsey (On a free to Juventus), Van persie (On a bargain to Manchester United, Alexis Sanchez (Swap deal for Mkhitaryan).
Obviously, signing some new defenders and wingers for the club is the main issue here. But, in my opinion, Arsenal have to really consider this a bigger issue. Imagine Arsenal end up signing a World Class Aaron Ramsey replacement for $50m+ and he turns out to be a great addition. Skip 3-5 years ahead, to the last year of his contract, Arsenal fail to negotiate a contract and lose him for free or on a bargain price. That would be the same story again.
Arsenal need to put the right men to negotiate a contract. They need to prioritise this issue.