Arsenal fans do not have many club legends to celebrate since the 'Invinicble' era of 2004 - and yet Wilshere can count himself alongside Thierry Henry and Dennis Begkamp as one of the most popular players in Gunners history.
This is despite announcing on Friday that his once-so-promising career is being sadly cut short at the age of 30.
Injuries denied Arsenal fans the full potential of one of their most talented academy products - and, in truth, the end was in sight for Wilshere long before he left the Gunners in 2018.
Nevertheless, his flashes of brilliance and deep connection with the north Londoners mean fans will always look back on his career with fond memories.
And a public disdain for arch-rivals Tottenham probably helps.
Arsenal whizz kid
Wilshere remains the youngest-ever player to feature for Arsenal in the Premier League after making his debut aged 16 years and 256 days old in 2008.
Dizzying heights were expected of the silky midfielder, who wowed fans and teammates alike with his stunning ability from such an early age.
Reflecting on his first days in training with the first team, Arsenal legend Ray Parlour recently recalled: "There were two players who stood out for me, Fabregas was one, and then Wilshere.
"He was only a young kid but he wasn't phased by Thierry Henry or [Robert] Pires or those sort of guys so I thought, 'This kid is going to be very, very good'.
"The thing is when you're 14-years-old, playing with such good players, you're going to be nervous but he wasn't, he looked like he wasn't phased at 14.
"Straight away you knew he had a lot of talent, he had a lot to learn, to improve as a player, and can you handle the big occasion, which he could.
"I thought, 'This kid's going to go all the way,' which he did, in the end he was in the side [at 16]."
Barca star turn
February 16, 2011 was the night that Wilshere truly introduced himself to world football with a sensational display against Barcelona in a pulsating Champions League showdown at the Emirates.
Wilshere, then just 19 years of age, ran the show for Arsenal in the middle of the park as late goals from Robin van Persie and Andrey Arshavin sealed a memorable 2-1 victory on home soil.
He produced a composed and determined performance that belied his tender years - and even joked that Xavi and Andres Iniesta were 'in his pocket' last year.
Speaking to Drive about the match, Wilshere said: "I played pretty much every game up to that. Played in the group stages and the Premier League, but that was definitely a step up to all of that.
"The midfielders were always close to each other, drawing you out and Messi would get it.
"I remember there was one minute in the game and I slid, I think it was on Iniesta, and won it and then took it past Busquets.
"I just felt the crowd lifted and I lifted my game from there."
Goals of the Season
Arsene Wenger famously adored Wilshere - so it's only fitting that he was involved in arguably the Arsenal manager's most beautiful goal.
Seventeen years in the making from Wenger's landing in London back in 1996, 'Wengerball' peaked with one of the game's greatest ever team goals against Norwich in 2013.
Kieran Gibbs harmlessly carried the ball into Norwich's half, offloading it to Santi Cazorla on the left touchline, and the Spaniard quickly decided it was time to get the party started.
Coming inside to find Wilshere, the ball was quickly returned to him, which he instantly sent to Giroud on the edge of the box.
The World Cup winner decided to have some fun with the pass, using his delightful touch to send it off the side of his boot and back to Wilshere first time.
Wilshere then decided to one-up the Frenchman's extraordinary technique, flicking his left boot up while on the run, glancing the ball back to where it came from.
Not to be beaten, Giroud opted to keep the outside of his shoe warm, dinking the return through a four-man crowd of yellow, for Wilshere to deftly guide in the goal of his career.
So good, it even made its way onto adult content websites.
His strike against West Brom in May 2015 wasn't bad either. In fact, Wilshere became the first player in Premier League history to win Goal of the Season twice in a row.
Hates Tottenham
What does Wilshere think of Tottenham?
From the day he led Arsenal's famous chant from an open-top bus, to his recent cameos on talkSPORT, those feelings have endured.
But Gunners fans will never forget the moment he truly cemented his place in club folklore at the 2015 FA Cup victory parade.
In front of thousands, Wilshere grabbed the microphone and asked the crowd what they think of Tottenham, before rather predictably getting their opinion of 's***'.
It led to a chorus of 'It's happened again' - and Wilshere was officially crowned a legend.
FA Cup winner
Besides immense popularity and cult-hero status, Wilshere also retires with a couple of trophies to his name.
The 30-year-old was part of the Arsenal side which ended their long trophy drought with back-to-back FA Cup triumphs in 2014 and 2015.
His career highlights also saw him travel to the 2014 World Cup with England and earn 34 caps for his country.
Despite his career being cut short early, most would settle for his achievements in the game.
Hates Tottenham
Did we mention Wilshere hates Tottenham?
At talkSPORT, we decided to put that to the ultimate test last year.
A presumably-quite-warm Wilshere is wearing lots and lots of different football shirts, all at the same time, in the studio.
Why? Because it was Football Shirt Friday and Wilshere was down for the cause.
To hammer home the message, Wilshere tried to set a new Guinness World Record for most football shirts worn at once.
Little did he know, talkSPORT host Andy Goldstein decided to throw a massive, cockerel-shaped spanner in the works.
The presenter convinced Wilshere the only way to break the record was to don a Spurs shirt, which the boyhood Gooner flat-out refused to do.
The line was drawn at Tottenham. And his stance was so firm, it was even enough to make Goldstein cave.
As the presenter later revealed, it was only a prank.
Arsenal through and through
Wilshere's biggest regret is leaving Arsenal, despite spending years on the sidelines before his eventual move to West Ham in 2018.
A loan spell at Bournemouth was not enough to win the favour of Unai Emery, following Wenger's departure, but Wilshere still wishes he tried harder.
"Honestly, I should never have left," he told The Athletic in 2021.
Wilshere is a rare breed who comes across more comitted to a single club than the game itself - and we mean that in the best way possible.
His return to Arsenal when training without a club and his new role as a coach for the Under-18s, which is set to be announced soon, show how much the Gunners mean to him.
Fans appreciate that kind of stuff.
Hates Tottenham
You get the point. But just in case…
Earlier this month, when asked what he would do if Spurs ever won the Premier League title, Wilshere delivered the perfect answer.
"I'm moving to Australia if that ever happens!"