It was after 2pm when the call came granting him permission to start a medical at Leeds United on deadline-day and make good his transfer from Swansea City.
Ten minutes before FIFA’s 11pm cut-off came the cold realisation that the move was dying a death.
James was in Yorkshire in plenty of time having been driven from Wales in the days earlier as Leeds and Swansea haggled over a fee and his early arrival implied that a deal was inevitable but there are orderly, scheduled deadline-day moves like the one Tyler Roberts completed from West Bromwich Albion 12 months prior and deals like James’ which hang in the balance for too long.
Leeds rarely see a signing go so close to the wire in January and have rarely been so angry about one falling apart.
For several days it appeared that Swansea were playing hard to get, knowing as they did that James wanted to take the offer Leeds were making him.
A source close to the winger told the YEP earlier in the week that the deal would “100 per cent get done” but discussions between the clubs went back and forward.
What began as a £5m up-front offer from United became a loan to the end of this season with a commitment from Leeds to sign James for a fee in excess of £5m if they won promotion from the Championship.
A loan fee was necessary to bring negotiations to a close. At that stage no-one saw the chaos ahead.
James passed a medical in good time at Thorp Arch and was driven to Elland Road around 6pm on deadline-day to complete the paperwork and go through the process of media interviews and photographs.
A late complication arose over United's initial intention to pay the £1.5m loan fee in June but sources at Elland Road insisted they were ready to commit to a revision of the scheduling and transfer an immediate sum of £750,000.
Leeds claimed to have been met with silence from Wales in the last hour-and-a-half of the window, creating the suspicion that the transfer was about to go under.
Swansea were in a delicate state, moreso than ever after their relegation from the Premier League, and it shaped up to be the deadline-day-from-hell for them.
By early afternoon they looked poised to relinquish James, Wilfried Bony, Leroy Fer and Jefferson Montero, an exodus which was asking for mutiny amongst their support.
Swansea owner Jason Levien is understood to have approved the sale of James directly with Andrea Radrizzani as part of an attempt to ease financial pressure and cut City’s wage bill but some in the boardroom at Swansea were opposed to the prospect of losing players as prominent as James and Fer.
Shortly after it emerged that James’ transfer had fallen through, the plug was pulled on Fer’s proposed switch to Aston Villa. Midnight passed and City released a statement claiming they and Leeds "could not agree suitable terms".
There were various attractions for James at Elland Road: an invitation to join from a club who were top of the same division as Swansea, were 17 games away from promotion to the Premier League; the chance to work with Marcelo Bielsa and the realisation that of all the wide options put to Bielsa before the January window open, the Argentinian singled out him; and roots in East Yorkshire where James was born, grew up and played academy football with Hull City.
Swansea, despite the interest he was receiving, allowed his contract to enter its final 18 months without attempting to discuss an extension five months ago and haven't since.
The 21-year-old was a schoolboy when Hull had him, snared by Swansea for £75,000 in 2014, but he has grown into a Championship winger who Bielsa believed he could hone and improve.
Bielsa called it a “significant transfer” as he waited for it to go through and was sold on what he saw of James in video clips given to him by Leeds: pace to burn and a will to attack as an out-and-out winger should.
It was on that basis that United put their eggs in one basket in the final week of the window.
The club’s scouting team identified alternatives to James but, with discussions with Swansea at a crucial stage, Leeds were set on signing him and no-one else.
Bielsa was ready to go empty handed, rather than see United pay too much for a winger who was in his first full season with Swansea.
James had 18 Championship appearances behind him at that stage and went on loan to Shrewsbury Town last season without playing once. Bielsa, as he likes to do, sized up his potential and advised Leeds to test Swansea’s resistance.
United’s head coach spoke at the time about the player Leeds were expecting to sign.
“Victor Orta (Leeds’ director of football) chose James and I accepted the player shown to me,” Bielsa said. “I agreed with the fact that this player has the features the team needs and responds to the needs of the team.
“The most important element is how he plays. After that comes his age. He comes into the group to compensate experience with youth. We have enough experienced players already.”
The signing of James would have tied in with the reshuffle Bielsa undertook after Samuel Saiz surprised Leeds in December by asking to quit the club and go home to Spain.
Saiz had been in and out of Bielsa’s starting line-up but, on his day, was a high calibre number 10.
Swansea’s decision to bring down James’ departure was not taken with impunity.
James was set on leaving before the deadline and went back to Swansea deeply disappointed by the club who blocked his transfer and left him sat at Elland Road while the grains of sand slipped away.
City chairman Huw Jenkins resigned in the following days over his role in the saga.
Leeds want to revisit the transfer in the summer should Premier League football come to Elland Road through the play-offs but James, for all his future potential, was a player Bielsa intended to unleash during the Championship run-in.