Jack Wilshere recalls season that could have led to Arsenal immortality

Having had a career that didn’t quite deliver on the early promise, Jack Wilshere could be forgiven for spending his days wondering what might’ve been.

Excellent performances for Arsenal‘s academy inevitably led to early opportunities for the first-team as manager Arsene Wenger gave a then 16 years and 256 days old Wilshere his first team debut in September 2008.

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That made Wilshere the Gunners’ youngest ever league debutant at the time and he became a first-team mainstay two seasons later.

There was seemingly no looking back for this precocious talent with a full England debut following later that campaign.

At the end of his playing career, in 2022, Wilshere finished with two FA Cup winners’ medals, a Community Shield and 34 England caps, while also playing for West Ham and Bournemouth.

It’s a career most pros would bite your hand off for, however, somebody of Wilshere’s talent may have expected more out of the game.

Wilshere’s not a case of a wonderkid who took his eye off the ball. Sadly, the football gods weren’t looking down on him kindly.

The midfielder was dogged by injuries throughout his career, with his knocks and strains keeping him sidelined for a combined three-and-a-half years of his 14-year playing career.

His constant injury setbacks culminated in retirement at 30 years old with Wilshere turning out for Danish top flight club AGF in his final act as a player.

No regrets – but one thing I think about

Now off the pitch for four years, Wilshere insists he has no regrets from his career but admits one thing he never achieved still occasionally plays on his mind.

Before Mikel Arteta’s Arsenal side were challenging for and eventually winning titles, Wenger’s men had one or two flirtations at glory after their Invincibles season of 2004.

One of them came in the 2015/16 season, the most iconic Premier League campaign of the lot where Leicester defied the odds to claim glory.

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The Foxes took advantage of all Chelsea‘s horror start as well as sloppy results for Manchester City and Manchester United to win with a couple of games to spare.

But amid all the outpouring of love across the country and world for Leicester, fans of those nearest to them rued the unprecedented opportunity.

It plays on the mind of Wilshere, with his Arsenal side the ones to come second in the table.

“I don’t really believe in regrets,” Wilshere told talkSPORT.com ahead of eBay Live’s 7 vs 10 showdown on Sunday.

“But I probably sometimes, like when you’re driving a car or you’re thinking about something on your own, it’s probably that year when Leicester won the league.

“I really felt like that was our year. We came close, I think we finished second, but there was a moment we beat Leicester at home. Danny Welbeck scored a header and I really felt like we can go on now and take it and we didn’t.

“So if there was one which I don’t like to believe in, it’s probably that.”

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New chapter

Not that Wilshere regularly has these thoughts, he’s got plenty on his mind as manager of League One Luton Town.

Taking the job in October 2025, the early parts of his spell at Kenilworth Road has been impressive with Wilshere’s men winning the EFL Trophy and miss out on a play-off spot by just a point.

There’s an innocence to Wilshere’s move into the management game as he explained: “I think back to my career now and I had some amazing highs, I had some tough lows as well. 

“But one thing that never went away from me and probably why now I’m pursuing the career that I am in, in coaching and management, is the love of the game. 

“My love for the game was always there and if anything, those low moments only made me want to do things more.

“Unfortunately, I had to stop my playing career because my body started to say no. But I’m really passionate and hungry to succeed in coaching and management. I think without those lows, maybe I wouldn’t be as hungry as I am to go on and do that.”

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Hosted by Jack Wilshere and Landon Donovan on Sunday at 2:30pm GMT, fans can tune in on eBay Live to bid live on curated memorabilia, football shirts, cards, and collectables tied to legendary No. 10s and No. 7s.