That scenario failed to materialise for the gifted former Arsenal playmaker whose career has been disrupted by injury and sees him as a free agent at the age of 28 following his release on transfer deadline day by West Ham United.
Now the prospect of Wilshere linking up again with Gerrard, his ex-international team-mate and someone he once described as his ‘role model’, is gaining significant traction.
While reports claiming talks between Rangers and Wilshere are ‘at an advanced stage’ are being played down by Ibrox sources, The Scotsman understands the move cannot be ruled out as the player weighs up his options.
Gerrard remains an admirer of Wilshere, just as he was when they were in the England squad together.
An example to follow
"Jack is so good I am sure when he gets to my age he will be in my position with the armband on talking about another 100-cap player,” said the Rangers manager back in 2013.
"It's his quality, his example in training every day. He wants to learn, he loves England.
"He ticks a lot of boxes when it comes down to other players following his lead. I'm really paranoid about putting too much pressure on any player but he is that good there is nothing for him to worry about."
Wilshere, in England’s squad alongside Gerrard at the 2014 World Cup Finals, has gone on to win 34 caps but has not represented his country since their calamitous Euro 2016 finals campaign in France.
His move to West Ham two years ago has failed to reignite his career but Wilshere insists he still has plenty to offer at a high level.
Wilshere: I still have lots to offer
"I'm still only 28 and feel fit, strong and ready to play,” he said this week. "I am still incredibly hungry, ambitious and desperate to play football and achieve success.
"Despite all my best efforts and intentions, it has not worked out as I expected (at West Ham). I have been fully fit for a large period of time at the club, including over the course of the last eight months - training hard every day - but unfortunately have not been given the opportunity to play.
"Although of course I am frustrated that I was not fully able to showcase what I am capable of at West Ham I remain convinced I can still contribute at the very top of the game.
"I'm now looking forward to the future and hope to be able to make an announcement about the next stage of my career in due course."
Wilshere’s next move ‘imminent’
While Gerrard expressed his satisfaction at the business conducted by Rangers during the transfer window, culminating in the deadline day capture of South African international midfielder Bongani Zungu on loan from Amiens, there is obvious appeal in adding the creativity of Wilshere to his options in that department.
Wilshere has suggested a decision on his next move is imminent and the lure of European football under Gerrard could prove decisive.