2019 is a significant year for Tottenham – they reached the Champions League final that season yet surprisingly, it was also the year Mauricio Pochettino was dismissed.
Despite all the remarkable work Pochettino did in north London, including transforming players like Dele Alli and Harry Kane into true stars, he left the Lilywhites without a single trophy.
So, what did Levy do next? He brought in one of the most successful managers of the 21st century, Jose Mourinho.
The self-styled Special One has proven himself in English football. A multiple Premier League and FA Cup winner, he’s also lifted the Champions League.
Surely he was the one to bring Spurs the trophy they longed for? Not quite. It all ended in disappointment.
Mourinho lasted only 86 games, with a points-per-match average of 1.77 – the third lowest of his career. That pretty much summed it up.
Mourinho’s Initial Signings at Spurs
The summer of 2020 held more promise. Despite the global pandemic, Mourinho brought in two players from Real Madrid to join the club.
Mourinho played a key role in bringing Gareth Bale back to English football, securing the Welshman’s return on a loan deal. Despite years of excellent service at Madrid, including scoring in a Champions League final and winning three La Liga titles, Bale was pushed out of the club.
Bale wasn’t the only player to arrive from the Spanish capital. Left-back Sergio Reguilon also made the move and began his Spurs career with a strong start.
In fact, analyst Raj Chohan acknowledged that the Spaniard was “unstoppable” at times, especially after delivering a top-notch assist for Bale’s goal in the 2-1 victory over Brighton.
Incredibly, after loan stints at Atletico Madrid, Manchester United, and Brentford, he remains contracted to Tottenham.
Why It’s Time for Reguilon to Leave
It’s been four years now—some might say challenging years—since Reguilon arrived under Mourinho’s management.
In his debut season, he proved to be a great signing, providing five assists across all competitions from the left side of the defense.
In 2021/22, he continued to make an impact in attack, scoring twice and providing three assists. However, Antonio Conte, known for his ruthlessness, wasn’t keen on him and sent him out on loan in 2022/23. Since then, the 27-year-old has struggled to make a lasting impression.
United only brought him in on loan due to a shortage of available left-backs, but the deal was terminated in January 2024. Brentford showed interest, and he played regularly there, but it wasn’t enough to secure a spot in Ange Postecoglou’s plans.
Reguilon, earning £53k per week, remains on Tottenham’s books but is essentially just taking up space at this point.
He hasn’t played a single minute this season, and for the benefit of all parties, he surely must depart in the January transfer window. Despite being included in the club’s 25-man Premier League squad, he was left out of their Europa League roster.
The Spaniard has gone from being a key figure under Mourinho, hailed as unstoppable at times, to someone with little to no chance of earning minutes at Spurs. His decline has been steep, and his future at the club looks increasingly bleak. Once a valuable asset on the left side of the defense, he now finds himself relegated to the sidelines, with his role at Tottenham seemingly non-existent.
For Tottenham, the only silver lining is that Reguilon’s contract expires next summer. With no real place in the squad and no future under the current manager, it appears that the end of his Spurs journey is finally in sight. The club can soon move on from this chapter, and for Reguilon, a fresh start may be on the horizon.
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