With his current deal expiring at the end of the month, Jack Wilshere has reportedly been offered a contract to stay under Unai Emery at the Emirates, but there are certain conditions to reflect his current standing in the game.
Given his injury record, the 26-year-old could suffer up to a £20,000 per week pay cut, and will only receive a bonus if he completes a certain amount of games per season, with bonuses, too, based on conditions as deep as minutes played.
Considering his questionable fitness, it seems unlikely that he will meet the conditions to gain the bonus, therefore putting him in a difficult position in the build-up to crunch-talks with newly appointed Emery.
Wilshere’s indecision suggests that he could still look for a move away from the Emirates to reinvigorate his career, but where?
1 AC Milan
Wilshere has been linked with a move to the Serie A, and Gennaro Gattuso's AC Milan appear to be leading the inquisition.
I think he can play in any league... I don't know how he's going to end up with his contract but I always admire him for his quality. -Gennaro Gattuso.
In the build-up to their clash against Arsenal in last month's Europa League quarterfinals, he stated that he "liked" him a lot, because he combines "English grit with Spanish technique" and can "play as both a support striker and a playmaker."
If Wilshere was to be snapped up by Milan, he would play in a more attacking, central position, giving him the licence to thrill further up the pitch, a position that has reaped him goals in the past for Arsenal.
The Serie A champions are also in the hunt for Wilshere's signature and have allegedly offered the English midfielder £4.5 million per season.
They turned their attention to him after having completed the signing of Liverpool's Emre Can and are now looking to snap up Wilshere on a free transfer too, to partner the German in the centre of midfield.
Wilshere would be a breath of fresh air in an ageing midfield and possesses both attacking flair and an eye for forward passes.
However, question marks loom over Wilshere's defensive discipline, a key aspect of the Old Lady's style of football. Moreover, Wilshere will have to compete against a well-stocked midfield, including the likes of Can, Miralem Pjanic, Sami Khedira and Blaise Matuidi.
From Wilshere's perspective, he's unlikely to see much game time in Turin.
The Merseyside team are looking to pounce on the fact he's not happy with his pay cut, and want to entice the Arsenal midfielder away from the Emirates, by convincing him they can break the top six and challenge for Champions League football- something Arsenal have struggled to do in the last few seasons.
If he was to make the move, he would join ex-teammate Theo Walcott and fellow England international Wayne Rooney in their efforts to enhance the attacking potency of Everton's attack.
Again, Wilshere will have to compete with a saturated midfield department, with Marco Silva still keen to get the best out of £40m-man Gylfi Sigurdsson.
Moreover, Silva's football is defensively minded and primarily counter-attacking, a style that Wilshere has not yet played in, hence there are no guarantees his skillset will suit it, or he has the fitness to match Silva's demands.
4 West Ham
West Ham appear to be the favourites to sign Wilshere.
If he makes the move from North to East London, it will provide him with what ex-Arsenal footballer Paul Mariner calls a "new challenge," allowing him to work with other attack-minded individuals, such as Marko Arnautovic and Manuel Lanzini.
I would like to see Jack go to a new club. I think at West Ham there are in a little bit of rebuild phase, new manager comes in. Get yourself out there, Jack. Show everybody what you have got. - Paul Mariner
Manuel Pellegrini, West Ham's new boss, is an attack-minded manager that enjoys possession of the ball, a style of play that will suit Wilshere given his time spent learning from Wenger.
Wilshere also went on loan to Eddie Howe's Bournemouth, another possession-based team, though the 26-year-old failed to make much of an impression, despite given licence as the Cherries' key figure in the middle.
What might be more beneficial is exposure to a completely new style of play, demonstrated by the revival in former teammate Alex Oxlade-Chamberlain's career, who flourishing since linking up with Jurgen Klopp's Liverpool.
These clubs, however, must remember that Wilshere comes with a risk.
His injury-prone nature has seen him miss an average of 12 games a season, due to a resurfacing ankle injury and several injuries to his calf muscle.
Wilshere has missed a third of games in each of his seasons in the Premier League, and unless these teams can keep him fit, he may cause them more damage than good, especially for the sort of wage packets reported.
The 26-year-old may have the potential to perform well at any of these teams, but he will need to be carefully managed to ensure that his history with injuries does not repeat.
Listen to the RealSport football writers discuss Group D in Kremlins in the Basement: RealSport’s daily World Cup podcast.
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