Tottenham were open to recruiting a left-winger in the summer transfer window - on top of the arrival of Xavi Simons - but club chiefs were unable to broker the right deal for Thomas Frank
Ademola Lookman's time at Atalanta once appeared to be the perfect marriage. In May 2024, the Nigerian's remarkable Europa League final treble to down unbeaten Bayer Leverkusen in Dublin saw him become the first player to net a hat-trick in a major European final since 1975.
But since then, it's been a bumpy ride in Bergamo for the 28-year-old former Charlton, Everton, Fulham and Leicester winger.
Last week, in the closing stages of the club's Champions League group phase clash against Marseille, Lookman was subbed by now-sacked boss Ivan Juric and the pair came to blows as the attacker left the field.
Atalanta later snatched a winner at the death through Lazar Samardzic and while the altercation was seemingly skated over because of the victory, Juric was sacked following his side's 3-0 Serie A defeat to Sassuolo last weekend.
Lookman wanted out of Atalanta in the summer and despite long-winded transfer negotiations with Inter Milan, a deal could not be struck to bring him to San Siro and he eventually stayed put.
Atletico Madrid were also attentive to his situation but with Lookman now swiftly approaching the final 18 months of his contract in Bergamo, there's a lingering sense that his future is likely to be resolved soon as his value is rapidly decreasing.
At 28, he does not fit Tottenham's usual transfer criteria but nobody can dispute he remains one of the best left-winger options currently available on the market.
He may also personally feel as if he has unfinished business in the Premier League after taking his game to the next level in Italy.
The left flank has been somewhat of a problem position for Spurs this term, despite Thomas Frank having a number of options within his current squad.
Tottenham looked at Antoine Semenyo in the summer but were put off by Bournemouth's excessive demands. Though looking back, the figures that were quoted at the time by the Cherries probably now look slim following Semenyo's explosive start to the campaign.
Mathys Tel, Wilson Odobert and Brennan Johnson have all shown flashes of promise but no player has really locked down the role and grabbed it with both hands. Xavi Simons has also been utilised on the wing at times, alongside centre-forward Richarlison.
However, if Tottenham are to kick on under Frank, it's clear they need a consistent source of goals and assists from the left flank, like they've had in previous times in Son Heung-min.
The South Korean icon is a legend in N17 and in many respects, remains irreplaceable but perhaps Lookman is an option that is worth considering, given he now appears to have entered the final chapter of his story with Atalanta.