His arrival from Aston Villa in June 2011—for a fee of £17 million according to BBC Sport—was greeted with a fair degree of fanfare by pundits who were keen to stress the versatility, set-piece delivery and potential greatness of the then 25-year-old as a top four starter.
There was even talk of how Young's signature was part of a master-plan—along with Luka Modric and Wesley Sneijder—to better Barcelona, according to David McDonnell for the Mirror football blog. Apparently he was also following a similar development trajectory to a young Cristiano Ronaldo, with his role likely to be through the middle rather than out wide.
For a while at least, the player who impressed at Villa Park, both on the wing and in a central role as a second striker, did show signs that his expensive summer switch may have turned out to be a solid piece of business for Sir Alex Ferguson.
In his league debut against West Bromwich Albion he was made Man of the Match for assisting Wayne Rooney and forcing an own goal, and opened his own account just two weeks later in United's 8-2 demolition of Arsenal, firing home two goals.
He was soon injured, however, and has never since quite matched the promise shown during his first few months at Old Trafford, although he hasn't always been as poor as his critics have suggested.
Unfortunately for Young, his position on the left wing could be considered hallowed ground for a sizeable number of United supporters who have grown accustomed to watching Ryan Giggs—the Welsh wizard himself—dismantle opponents down that flank on a regular basis.
Considering too the other heroes who have dominated that side of the pitch, from Jesper Olsen in the 1980s, to Giggs' fellow '90s wonder boy, Lee Sharpe, and even the injury-ravaged Jesper Blomqvist; all were taken to heart by the Stretford End for their spectacular wing play.
Later on in the 2000s, as Giggs sought to reinvent himself, the left flank was the stage upon which Crisitano Ronaldo announced himself to the club while Nani has also occasionally delighted the crowds on his less favoured side.
Even Park Ji-Sung endeared himself to the crowds from the left with his big-hearted, big-game displays even if he lacked the magic, grace and individual brilliance of his more outlandish colleagues.
While these crowd favourites may have come and gone, United fans have grown fond of being presented with such talents, brimming with confidence and class, as they ply their glamorous trade down the left wing.
How Young Can Win Back the Fans and His Place
Regain His Confidence and Cut Inside
Ever since his injury Young has struggled to live up to United's left sided lineage, with his right-footedness—the source of his two goals against Arsenal as he cut inside and shot from range—becoming a hindrance as he began to play within himself.
Once his head dipped, so did his courage, and he came to prefer to take the ball to the byline rather than venturing into the channels or central areas.
Rather than being able to unleash his right peg against opposition keepers, or thread a first-time through ball into the box for a runner, out wide his need to take a touch, turn around and reposition himself in order to deliver a cross with his stronger foot makes him all too easy to defend against.
It seems unlikely to come about considering his struggle to secure a regular run of games these days, but Young would likely fire himself straight back into contention if he were suddenly able to forget about his failures and rediscover the perkiness he showed in 2011.
A regular goal-scoring threat from out wide would be greatly received by David Moyes, who currently needs all hands to the pump if United are to finish in the Champions League places this season.
Young's loss of adventure when going forward has also affected how well he combines with his fellow players too.
Work on His Link-Up Play
Again, there is a precedent that he is expected to somewhat live by, or at least measure up to: Giggs' understanding of his treble-winning midfield colleagues Roy Keane, Paul Scholes and David Beckham, one of the most naturally balanced ensembles ever to grace a football pitch.
That midfield—so complete and well-rounded—was a classic of its genre; the game's answer to the effortless chemistry of Friends or Seinfeld and their ensemble casts, whose traits and personalities melded together with an almost effortless and irresistible chemistry.
Sadly, while Giggs has gone on to revitalise himself as United's elder statesman in central midfield—like Larry David and his post-Seinfeld success with Curb Your Enthusiasm—Young's attempts to follow in Giggs' footsteps have instead gone the way of Joey Tribbiani: a misguided spin-off.
Rumours suggest that he may be sold off in January according to David McDonnell of the Daily Mirror, it appears that the winger has been written out of his production's script like so many other failed protagonists thrust upon a series.
After all, The Simpsons did away with psychiatrist Marvin Monroe, Harry Enfield and his character Dermot Povey lasted just one series on Men Behaving Badly, and Emily Waltham—Ross Gellar's English love interest in Friends, as portrayed by Helen Baxendale—was hated by the show's fans.
The reaction to Young's appearances this year, both in the starting line-up or off the bench, has been one of groans of dismay rather than cheers of joy and hope.
Compare his deflated attempts to assert himself with the fearlessness of Adnan Januzaj, who has been a mini-revelation down the left when given the chance to play.
With his head up, attention focused and hunger for success yet to be sated, the Kosovar-Albanian has slotted into an inconsistent situation well, combining with Wayne Rooney, Robin van Persie and Patrice Evra to great effect.
Young has found it hard to strike up such a rapport on the field of late, even though he remains a popular member of the squad judging by the brief, behind-the-scenes footage drip fed by the club's official site and social media campaigns.
Such a yardstick for measuring his relationship with his teammates is hardly scientific, but there doesn't seem to be any malice or hesitation to play Young into games either. The bigger problem is the winger's reluctance or inability to make sufficient space for himself or take up the best positions to encourage greater inter-play.
Build on His Existing Relationship With Supporters
Adding further disappointment to Young's decline since joining the club is the sense that, off the field, the winger really does get what it means to be a United player.
During his injury lay-offs Young has often been spotted in amongst the fans on away days with his presence noted at St James' Park and the Etihad that year.
United fan and news site, The People's Person, carried the story of his surprising appearance in the stands during a game at Newcastle United in 2012, with the sidelined new signing even joining in with the chants.
His presence off the pitch at another away match at the Etihad, alongside Tom Cleverley and Darren Fletcher, was captured on video.
Recently too Young has garnered something of a goodwill boost after responding directly to a request to help a terminally ill fan visit Old Trafford to catch a game.
Even more impressively, Young's reply was only his 31st tweet with the original help message sent out completely unsolicited and without the player being tagged into it, which suggests he must have either been searching for the right term at the right time or is an avid follower of fan activity online.
While continuing to impress supporters with his attitude as an ambassador for the club is unlikely to have any bearing on Moyes' team selections, getting the fans on his side could be a vital first step in rebuilding that confidence which is so key to the previous two points.
If All Else Fails, Play Like Park
Considering Januzaj's emergence it's unlikely Young would be the most exciting left winger in the squad even if he were to rediscover his form.
With Shinji Kagawa and Wayne Rooney wrestling over the No. 10 role, it's unlikely that the former Villa support striker would get a look-in in the hole.
Do you see a future for Ashley Young at Manchester United?
Yet there is a niche that is yet to be filled within the current United squad, and it could be one that feeds directly into Moyes' cautiousness and tendency to trust in hard-workers rather than unreliable flair players.
The man signed by Sir Alex to add greater flexibility to his attack should become a defensive forward player in the mould of Park, harrying and harassing opponents to win the ball high up the pitch while covering for Patrice Evra's constant attacking on the overlap.
Based on his usual displays, Young is already a fairly diligent player who is happy to track back if not throw himself into tackles at every opportunity.
Should he decide he wants to stay at Old Trafford at all costs, honing that side of his game into a right-footed, left-wing destroyer rather than creator could see his stock rise in the eyes of his new, pragmatic manager.