Now, five years later, he finds his career at a crossroads following yet more loan misfortune.
Last week’s scrapping of the National League campaign aborted May’s latest bid to kickstart his football.
At the start of the season, Swindon had been earmarked as the League Two stage for the midfielder to shine through regular first-team involvement.
The scheduled season-long stay represented a precious opportunity for the Academy product, eager to prove his worth in the Football League following two previous non-league loans.
Disappointingly, the outcome was just 13 appearances for the promotion challengers, of which one start arrived in league action, naturally prompting his Fratton Park recall in January.
Since February, Boreham Wood has been May’s home, yet that has also now been ransacked.
The 22-year-old is out of contract at the end of June – and faces a battle to remain on the south coast irrespective of when next season begins.
Certainly this term’s frustrating loan spells will have done little to convince Kenny Jackett to extend the Pompey stay of a player who has made 30 appearances for the club.
May, of course, still possesses that potential. The midfielder is blessed with an elegant on-pitch demeanour, capable of accurate eye-catching long-range passing, an attribute perhaps lacking from the current side.
There have been first-team glimpses too, his magnificent display in the 2-1 Checkatrade Trophy triumph over Arsenal under-21s in December 2018 immediately springing to mind.
Then there was involvement at Fleetwood in February 2018, striking the bar from distance with a sumptuous strike which would have capped an impressive League One performance for Jackett’s men.
It was under caretaker boss Gary Waddock when May was handed a debut from the bench in April 2015 during a 1-0 home defeat to Bury.
Aged 17 years, four months and 13 days, he became the latest Academy product given senior recognition that term, following in the footsteps of Close and Chaplin.
The pair, admittedly weighing in at least a year older than May, have progressed to each register in excess of 170 appearances for Football League clubs.
Meanwhile, May has fallen considerably behind Jackett’s central midfield options and, as a consequence, his make-or-break campaign is heading towards a heartbreaking finale.
Unless the manager has one last shot at a now prodigiously talented 22-year-old finally blossoming.
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