It would be the most unexpected twist if Archie Gray dropped down to the Championship with Tottenham Hotspur just two years on from his decision to depart Leeds United.
In his mind, the versatile midfielder was leaving to progress his career. He was heading to a top-six Premier League club to play in a free-flowing Ange Postecoglou side at the time.
Two years later, however, Leeds sit above Tottenham in the top flight and Gray may be regretting his decision.
At 19 years old, however, the future is still bright for the former Leeds graduate even if those in North London continue to struggle in the Premier League.
Will Gray regret Leeds departure?
Whilst Gray does have a Europa League medal to his name, he would have been expecting to put relegation scraps behind him after leaving Leeds in 2024.
As it turns out, though, there wasn't a worse time to join up with the Lilywhites, who paid £30m to secure his signature from Elland Road. In the space of two years, the teenager has already played under three different managers, with Igor Tudor the latest coach tasked with navigating the club out of danger.
For Leeds, Gray's exit followed the heartbreak of missing out on promotion in the 2023/24 campaign. It spelt the end for one of their best academy graduates and the end for a third-generation Elland Road star.
There's no doubt that he would have a place in Daniel Farke's current side. After all, Gray is capable of playing right-back, defensive midfield and central midfield - featuring in all three roles at Spurs despite his tender age.
There will still be some regrets over his departure, but it could be argued that it was another young player who slipped through Leeds' grasp.
Whilst the focus is often on Gray, Charlie Cresswell's recent rise suggests that the Whites made a mistake without even realising it at the time.
Charlie Cresswell should be Leeds' biggest regret
When Cresswell swapped Leeds for Toulouse in 2024, he left Elland Road without ever really receiving a consistent opportunity.
He was not like Gray, who was a mainstay in Farke's matchday squad. Instead, he was on the periphery and featured just 14 times for the first team.
The central defender proved that he could cut it in the Championship, too. Cresswell impressed on loan at Millwall. Yet, still, his chance didn't arrive at his boyhood club.
Now, fast-forward two years, and the 23-year-old is worth more than every player at Elland Road right now. He has gone from Leeds struggles to one of the most promising young defenders in France, who's on the radar of Liverpool and others in the Premier League.
After impressing for England U21s on their way to victory at the Euros last summer, Cresswell has only kicked on even further. Reportedly valued at around £26m at Toulouse, there's every chance that Leeds could be bumping into a familiar face in the Premier League this summer.
To put that price tag into context, no player in the Leeds squad, according to Transfermarkt even comes close. Indeed, Anton Stach and Ethan Ampadu come out on top at Elland Road, worth around £17.5m each.
A bully of a defender, no player has made more clearances than Cresswell in Ligue 1. The Englishman has taken France by storm ever since arriving and, with every impressive performance, Leeds' feeling of regret continues to grow.
Although it was Gray who stole the headlines with his departure in 2024, Cresswell is arguably proving to be an even greater loss at Elland Road.