Gray's move to Griffin Park was so advanced in the summer of 2024 that he underwent a medical with Brentford before Tottenham hijacked the deal at the eleventh hour, eventually paying £40m to make him the fourth most expensive 18-year-old in football history.
Tottenham have shown no appetite to let him go this time, having already turned down interest from Newcastle earlier in the window.
Gray, now 20, has started the season at right-back rather than his preferred central midfield role, lining up there in the opening-day defeat at Brentford and again in Saturday's home loss to Newcastle.
That positional mismatch may be part of what has caught Brentford's eye, given competition for a midfield berth at Tottenham has intensified sharply this summer with the arrivals of Sandro Tonali for £100m and Mateus Fernandes for £85m, joining an already crowded engine room featuring Rodrigo Bentancur, Lucas Bergvall, Conor Gallagher and Gray himself.
Whether Brentford's interest develops into a formal offer remains to be seen, and even if it does, Tottenham's resistance to selling their young captain is expected to hold.
Gray became Spurs' youngest ever competitive captain when he wore the armband in that opening-day defeat at Brentford - the very fixture that offers a neat symmetry to his old suitors' renewed pursuit.
Gray's versatility, having played across midfield and both full-back positions since coming through Leeds' academy as a child, has always been central to his appeal, but it has also occasionally worked against him at Tottenham, where manager Roberto De Zerbi has preferred to use him as defensive cover rather than in his favoured deeper midfield role.
For now, a move remains speculative rather than advanced, with Tottenham giving no indication Gray is available at any price this window.