At the age of 19, Wilshere was named as the 2011 PFA Young Player of the Year, prompting him to be hyped up as the main man for Arsenal following the departure of Cesc Fabregas.
After being honoured with three awards in his first full season at the club, Wilshere was thought to be one of England's brightest prospects.
Five years later, the same individual has gone on to join AFC Bournemouth on loan in a bid to revive his career.
To me it doesn't make sense, staying in the league that relies on physicality which isn't Wilshere's key strength and remaining close to the English media that produces nothing but negative reports towards him.
With Arsene Wenger now having the option of choosing from Granit Xhaka, Mohamed Elneny, Santi Cazorla or Aaron Ramsey as Arsenal's first choice central midfielders, it makes it very difficult for Wilshere to force himself into the team especially considering the bad luck he has experienced with injuries over the past few years.
A lack of game time in recent years is the glaring reason why a temporary move away was needed in order for him to turn his career around.
To many, Wilshere moving to the Cherries was ideal so he can stay in the same culture and competition, but what happens to his career if he fails at Bournemouth? Wenger will have no choice but to sell him next summer if the next nine months do not go as planned.
That is something the Arsenal faithful won't like to see, that one of their one boys isn't quite good enough if he doesn't produce the performances that are to prove everyone wrong this season.
Since completing the fairy-tale rise to the Premier League, Bournemouth's style under Eddie Howe is attractive, pass and move, attacking football which is very similar to when you watch Arsenal – a key point to why Wilshere chose them ahead of other clubs.
The difference is that the former aren't realistically going to dominate games similar to the latter.
Perhaps the 24-year-old should have considered a move to Spain - namely with either Sevilla or Villarreal - which would have got the best out of the Englishman who is recognised as a key man to dictate play.
The midfielder who keeps things ticking, if you will.
Being an English player from a top side like Arsenal, it's easy to receive several Premier League loan offers; at the same time experiencing a different culture over in Spain, or Italy, could have possibly changed the typical attitude that leads him to many problems that the general UK media consistently tend to report.
Wilshere going out of his comfort zone would have helped him in the long run, choosing to play in a league that suits him ahead of the biggest league in the world.
The fact that Wilshere needs to find himself as a player again would suggest a move to a league he can thrive in such as La Liga would have been a clever, yet not quite straightforward choice for him.
Looking back at the performances he has produced over the years when he has been fit, it's clear to see that the 34-time England international hasn't declined but simply hasn't developed, keeping in mind he can still play five to seven years at the highest level of football.
A potential move to La Liga was always going to have Wilshere under pressure, especially after making only ten league starts within the past two years due to injuries.
Alongside that, settling into a new league and new culture may have been tricky for the boy from Stevenage.
Manchester City's Joe Hart left England to play for Serie A side Torino the same day Wilshere moved to Dean Court, so why couldn't the midfielder follow the goalkeeper's example and attempt to benefit from experience abroad?
Barcelona icon Xavi, an individual who has always praised Wilshere, mentioned the midfielder in a recent interview: "He is a young player still, and if he can put the injuries behind him, there is no reason why he still can't be one of the best midfield players in Europe."
Ties should be severed to give all involved a fresh start.
But only if his time on the south coast is a flop as he is really a sublime talent who may yet have a glittering career in North London if he can rediscover his game-changing best with the minnows of the English top flight.