When Trent Alexander-Arnold announced that he would be leaving Liverpool, shortly after helping the Reds win the Premier League title, many felt his imminent move to Real Madrid would catapult him to new heights as a player.
Fast-forward to now, however, and the 27-year-old's decision to roll the dice by leaving his beloved Merseyside for the sunny shores of Spain appears to be backfiring.
Alexander-Arnold was a key player for Liverpool during his time there. He became a regular under both Arne Slot and Jurgen Klopp, established himself at international level and won countless titles such as the league, Champions League, FA Cup and Carabao Cup.
Earlier this year, however, he decided it was time to pursue a new challenge elsewhere. When Real Madrid come calling, players tend to listen. Alexander-Arnold, clearly, heard enough to convince him that the Bernabeu - rather than Anfield - was the place to be.
On Tuesday evening, the England international returned to his old home for the first time since controversially flying the nest. Rather than be welcomed back with open arms, however, it was quite the opposite.
Liverpool fans booed and jeered as his name was read out prior to the clash, the success he was pivitol in forgotten. When he came off the bench, with mere minutes remaining, the hostility continued.
To make matters worse, Real were a shadow of their usual selves as they slumped to defeat. Kylian Mbappe was flat, Jude Bellingham uninspiring and Vinicius Jr subdued. In the end, a header from Alexis Mac Allister in the 61st minute proved to be the difference, giving the hosts a huge victory while rubbing salt into the wounds of their former soldier.
Trent Alexander-Arnold is hoping to win the Champions League with Real Madrid
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Trent Alexander-Arnold endured a tough return to Liverpool on Tuesday night
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Even prior to the match, a mural featuring Alexander-Arnold was vandalised in Liverpool. It was never going to be a straightforward return from that moment on.
It compounds what has been a difficult start to life in his new surroundings for the right-back.
Alexander-Arnold joined Real shortly before the Club World Cup, with the LaLiga giants forking out £10million to secure his signature early so he could play in that tournament.
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Trent Alexander-Arnold came off the bench during Real Madrid's Champions League defeat to Liverpool
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But Real's hopes of glory were ended by Paris Saint-Germain in the semi-finals, with the Ligue 1 team winning 4-0 courtesy of a brace from Fabian Ruiz and further efforts from Ousmane Dembele and Goncalo Ramos.
In LaLiga, Xabi Alonso's men have been soaring.
They have won 10 of their 11 matches, with a defeat to fierce rivals Atletico Madrid the only blot on their record.
Yet Alexander-Arnold's own campaign has been marred by injury.
Before last night's epic European fixture, his last appearance for the club had been in a 2-1 Champions League victory over Marseille. Even before that, however, he'd started to fall behind Dani Carvajal in the club's pecking order.
Carvajal, even at the age of 33, is far from finished. He remains one of the best right-backs in world football and, rather than shy away from the challenge of keeping his spot in the team, he's embraced it.
Dani Carvajal and Federico Valverde are currently above Trent Alexander-Arnold in the Real Madrid pecking order
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But even when the veteran isn't picked or available, Alexander-Arnold doesn't appear to be the next-highest in the pecking order.
Instead, that honour has gone to Federico Valverde. A midfielder by trade, he has filled in at right-back in the past and done an admirable job.
There is, of course, no sign of Alexander-Arnold leaving Real just yet. The hopes is that, when he's fully fit, he can kick on and become a key figure for many years to come.
So far, that's yet to happen. Whether he can silence the boy boos by returning to form in the coming weeks and months remains to be seen.