The first, the old and the new Jack Wilshere

Published by

Jack McRae

on

16th Oct 2025

_{^{Jack Wilshere spent most of his career at Arsenal and played alongside the current Gunners boss Mikel Arteta. Photograph: Wikimedia Commons / joshjdss}}

Who is this Jack Wilshere? A question many would have asked when I first saw him kick a ball in a pre-season friendly against a Real Madrid midfield of Wesley Sneijder, Lasanna Diarra and Guti. The diamond of Hale End was only 16 when he entered the Emirates pitch and a world of gleeful expectation.

That first Jack Wilshere, the one who had been shaped and moulded by the Gunners’ academy from the age of nine, had been shielded from the spotlight and scrutiny. That chapter would be quickly closed when, at just 16 years and 256 days old, he made his competitive debut for Arsenal, becoming the club’s youngest-ever league debutant in a 4-0 win over Blackburn.

The next Jack Wilshere, the one who would go from a teenage sensation to a man gripped by injuries and failed promise, would become the epitome of Arsenal’s nearly-men, dreaming of what could have been. A time brought to a spluttering stop by his own body, forced to hang up his boots at just 30-years-old and turn to coaching.

Now, 17 years and 18 days on from that game at Ewood Park, Wilshere enters the third stage of his life. Named on Monday as the new manager at Luton Town, he insisted: “This is a new Jack Wilshere, a different Jack Wilshere, who is hungry to achieve great things.”

What can we expect the third Jack Wilshere to achieve in the next 17 years? It is hard to predict. Just as he did his playing career, Wilshere enters the coaching world as one of the youngest on the block, only Brighton’s Fabian Hürzeler and Southampton’s Will Still are younger in England’s top four divisions, with a tricky challenge on his hands.

*_{^{Jack Wilshere broke into the Arsenal side as a teenager before injuries stalled his career. Photograph: Wikimedia Commons / Wonker Wonker.}}*

Wilshere has been tasked with halting the Hatters’ dangerous slip and slide down the football league before they find themselves back in League Two for the first time since 2018. The gamble Luton are taking cannot be overstated: they are trusting a man who has just two games of senior football as an interim head coach at Norwich to turn their sinking ship around.

That is not to say it won’t work. While he is a different man to the 19-year-old who fearlessly bossed a midfield of Xavi, Sergio Busquets and Andres Iniesta, being thrust under the digital magnifying glass with every minor scruple blown up to the max is not new.

Nor even is coaching. He drew countless plaudits when overseeing 60 games in charge of Arsenal’s under-18s side, working with the likes of Ethan Nwaneri and Myles Lewis-Skelly, and guiding them to the FA Youth Cup final. When Mehmet Ali left the under-21s this summer, Arsenal wanted to bring Wilshere back to take over the vacancy.

Appointing novice coaches is also a well-trodden ground in League One and Two, with the hunt to find the next Kieran McKenna bringing mixed results. The Ipswich boss was Manchester United’s assistant manager, with only 50 games in charge of the Red Devils’ under-18s, when he was named as the Tractor Boys’ permanent boss. McKenna then oversaw back-to-back promotions and took Ipswich back to the Premier League for the first time in two decades.

League One is littered with forgotten, familiar faces in the dugout. Conor Hourihane, Lee Grant, Noel Hunt are all in their first gigs as managers at Barnsley, Huddersfield and Reading, respectively. Stevenage’s Alex Revell and Cardiff’s Brian Barry-Murphy are in only their second spells as full-time bosses and occupy two of the top three spots in the division.

Of course, just because the McKenna blueprint has worked in some places, does not mean it will work in others. Wilshere is a far more prominent name than any of those managers mentioned above and the sheer volume of media coverage that comes with him simply being associated with the job adds a heavy weight of expectation.

*_{^{Jack Wilshere’s antics after FA Cup successes cemented him as a hero amongst Arsenal fans. Photograph: Wikimedia Commons / DSanchez17.}}*

Everyone has their idea of who Jack Wilshere is. From the boy with the world at his feet, to the Jack-the-Lad figure goading Tottenham to the eventual broken journeyman clinging onto the last drops of lost potential squeezed out ruthlessly by crippling injuries.

Unlike 16 years ago, ‘Who is this Jack Wilshere?’ is not a question many will ask on Saturday. It is not quite Real Madrid, but when the young coach takes the Kenilworth Road dugout against Mansfield, he enters a new, different world.

But, as he says, this is a new, different Jack Wilshere.

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