A little over two years ago the youngster was sent back to Swansea after failing to make an impact in League One at Shrewsbury Town.
Fast-forward to this summer and speed demon James, 21, is now a full Wales international having scored on his debut and shone for the Swans in the Championship – almost sealing a £10m January switch to Leeds.
All of this after he failed to break into Paul Hurst’s first-team plans at Shrewsbury and – last summer after not making any splashes at his parent club – almost left to join League Two Yeovil on loan.
But why did James not stay at Montgomery Waters Meadow to win a place in Hurst’s side?
Had James blossomed in League One, he might have been the added X Factor that helped Hurst’s heroes over the line to automatic promotion to the Championship.
Yorkshire-born James was 19 when he sealed a season-long loan to Salop on June 30, 2017, his first loan move for a taste of senior football.
He was in the final stages of recovering from a double hernia operation.
He featured in a couple of friendlies and showed flashes of his speed.
He was just the second of what turned out to be six loan deals through the door that summer – Hurst only wanted the five eligible to feature in an EFL matchday squad.
Shrewsbury had five loans in their ranks in the form of James, Ebou Adams, Dean Henderson, Carlton Morris and Niall Ennis before a sixth target suddenly became available late in the window.
Highly-rated Norwich youngster Ben Godfrey had been a target of Hurst’s, like Henderson and Morris, in previous windows and Town tried and tried again for his services.
The Canaries’ answer remained ‘no’ until August 22, three games into the League One season – Shrews had won them all.
Town had just won a behind-closed-doors friendly against Walsall – ironically James caught the eye of staff and team-mates in front of an empty Meadow that day – and Hurst had finally had the green light from Norwich on Godfrey.
But with five loans in, Hurst was told there was no room in the budget to accommodate for Godfrey.
Meanwhile, young James had struggled to settle in Shropshire. He was behind on fitness and struggling to integrate before becoming frustrated with his form.
Hurst and Chris Doig knew the flying winger – now said to be as quick as French superstar Kylian Mbappe – had speed to terrorise third tier defences, but had not managed to adjust to his move.
Town’s management were desperate to bring in versatile youngster Godfrey, who had played right-back and centre-half for his parent club but would go on to dominate in a different position for Salop.
So Shrewsbury chairman Roland Wycherley decided Godfrey would be a worthwhile addition to the 2017/18 group and sanctioned the move – only if one loanee was to leave and free up space in the kitty.
Godfrey checked in on Thursday, August 24, and made his debut two days later at Oxford where he ran the midfield and immediately looked every inch a tailor-made midfield enforcer.
Incidentally Shrews put in one of the best displays of a memorable season despite drawing 1-1 that day.
And that was that for James, who made way for Godfrey in Town’s squad, with the winger returning to south Wales before the window closed on August 31.
What he went on to achieve for Swansea and his nation could not have been foreseen, but Town are right to wonder what could have been.