This article is part of Football League World's 'Terrace Talk' series, which provides personal opinions from our FLW Fan Pundits regarding the latest breaking news, teams, players, managers, potential signings and more...
Leeds United supporters will always wonder what could have been with Archie Gray, who left for Tottenham Hotspur over the summer after just one season in the first-team fold.
The Whites ultimately fell short in their ambitions of returning to the Premier League at the first time of asking last season, losing out in the Championship play-off final to Southampton. Leeds' player retention power was subsequently weakened tenfold, with Gray departing in a hectic summer transfer window alongside the likes of Glen Kamara, Crysencio Summerville and Georginio Rutter.
A member of the vaunted Gray dynasty at Elland Road, the teenager had long been poised for a glittering future during his progression through Leeds' academy system and eventually vindicated just that.
He enjoyed a stunning breakout season during the 2023/24 campaign and made 52 appearances across all competitions, the majority of which came at right-back as opposed to his favoured central midfield position.
Gray, who was just 17 years of age for the majority of his first and only season in the Whites' first-team, promptly earned a move to Tottenham Hotspur at the start of July. The deal was reported to be worth £30 million, with Joe Rodon heading the other way on a permanent basis after spending the previous season on loan with Leeds - the entire package was said to be worth around £40m to Leeds.
Leeds United, Archie Gray regret claim
We caught up with our resident Whites fan pundit, Kris Smith, to ask if there was one past player he wished to have seen more often for his club.
"I think a player every Leeds fan wishes they saw more of before he left was Archie Gray, because there's no telling how far he could go in the game and how little we're actually going to end up seeing of his career," Kris explained to Football League World.
"£40 million is obviously an awful lot of money in the Championship and you can't really turn that down, especially in our position after missing out on [promotion through] the play-offs.
"But he's going to be worth a hell of a lot more soon enough if he keeps developing the way he is. He's already showing his quality at Tottenham in any position he's played in, whether it's left-back, right-back or even in central midfield.
"The fact we only got to see him for one season is such a shame, and it was a season where he was playing at right-back instead of central midfield as well, and he was 17 for most of it.
"There's a strong feeling of jealousy with Leeds in terms of watching on and seeing him play for Tottenham at the moment.
"I think it comes from the fact that we know we could and should have been in the Premier League this season and having Gray developing as one of our own into someone that is destined to play for England and start every week."
Leeds United will regret 23/24 promotion failure
The Whites are sure to be among the promotion reckoning once again this time around, but their failure to complete the objective last term dealt them with devastating consequences.
Of course, there can be no absolute guarantees that they would have been able to retain the likes of Gray, Rutter and Summerville had they achieved promotion. However, Leeds undoubtedly would have stood a much better chance.
They would not have been forced into generating as much money in player sales as they did, while having a status as a Premier League team could well have convinced their prized assets to stay put in West Yorkshire.
The optimists may attest that Leeds deserve credit in the first place for developing talent and returning profits in the first place, and that line of thinking is far from false. However, supporters will always be haunted by the nagging thought of what could have been, which may only ring harder if Gray develops according to expectation at Spurs.