It has been more than eight years since Jack Wilshere burst onto the scene as a highly promising 16-year-old. Wilshere’s performances as a teenager led many to believe that he would be the long-term replacement for Cesc Fabregas at Arsenal and a mainstay in England’s central midfield. However, Wilshere’s form, injury proneness and, arguably, his attitude have all played their part in stalling his development; culminating in this season’s loan switch to Bournemouth and question marks over his Arsenal future. This uncertainty hasn’t gone unnoticed and various clubs are keeping a close eye on Wilshere’s situation, most notably Italian giants AC Milan. A move away from the Emirates seemed unthinkable a year or so ago, especially overseas, but could a move into the continent be the remedy to revive Wilshere’s floundering career?

Now, most pundits and fans would probably argue that the most sensible option for Wilshere is to get a full season under his belt at Bournemouth, sign a new contract with the Gunners, and then fight for his place back in the team. That does make logical sense; Arsenal are at the top level, he’s loved by the fans, and he will comfortably fit back into familiar surroundings. However with too much comfort comes less desire to drive on, and as the famous business quote goes “growth is always made outside of the comfort zone”. Arsenal as a club are in a state of plateau, and it is this safe culture that could hinder Wilshere’s development even further. A move to a club with a more intense and aspirational mentality could provide Wilshere with the step change that his career so badly needs.

This is where Milan come in. Currently, you’d be hard pushed to find a more intense and aspirational club than AC Milan. Although still, the most successful club in Italy, Milan have fallen from grace quite dramatically in recent years. The match fixing scandal of 2006, ownership issues and the general demise of Italian football have all greatly impacted Milan’s capabilities of both signing and retaining top class players. The Rossoneri have just 2 Serie A titles to their name since 2004, the last coming in 2011, and since that glory, they have fallen well behind the likes of Juventus, Roma and Napoli. However, a powerhouse club like AC Milan with their incoming Chinese billionaire owners could match any club for wages, and there are legitimate reasons why Wilshere should consider the advances of the Italians.

Since slipping out of Europe’s elite, Milan have been in a busy rebuilding process and are on a steep upward curve. The squad is young and the 42-year-old manager Vincenzo Montella has the team playing a style of football that is well suited to Wilshere’s own technical game. Following some investment in 2015, Milan finished 7th last season and after 17 games this season find themselves in 5th place – just 2 points off 2nd place. So it could be that next season we see the return of AC Milan to Europe’s premier competition – Champions League nights in the San Siro, there can’t be many better experiences in football than those.

When it comes to looking at Wilshere personally, he has all the characteristics and qualities to make this move and transition into another club. Wilshere’s technical ability has always been excellent, but he also possesses the drive, passion and confidence to blend into any team and any set of teammates. Wilshere would also arrive as one of the more senior players in this Milan side and would be one of the first names on the team sheet. Yet despite Wilshere’s highly regarded reputation, he’s still somewhat of a rough diamond, still capable of building his game by adding goals, improving his range of passing and authority on the ball. Therefore, joining Milan as an integral cog with the team built around him would provide the freedom Wilshere requires to flourish and develop into the true player he is meant to be. Wilshere really would be a big fish in an even bigger pond.

Jack Wilshere is at a crossroads in his career. Like Arsenal as a club, Wilshere is stalling and going through the motions. If Wilshere really wants to achieve his potential, then something needs to give. The supposedly safe option is to stay at Arsenal and fight for his place; but what if it continues to not work out and this opportunity passes by? A real change needs to happen for Wilshere to truly re-ignite his career and grasp hold of his destiny as a footballer. The loan move to Bournemouth looks to be giving Wilshere his mojo back and, hopefully, the confidence to make a big leap out of the cosy crèche of Arsenal and into the ambitious, fiery cauldron of San Siro. Jack, andare a Milano.