Tottenham Hotspur chairman Daniel Levy has a well-earned reputation as a tough negotiator.
Manchester United certainly knows how much of hard ass he can be. The club endured long, protracted negotiations for Michael Carrick in 2006 and Dimitar Berbatov in 2008 — the latter was such an ordeal that Sir Alex Ferguson later said it was more painful than his hip replacement surgery.
In subsequent years, Levy seemingly went out of his way to make sure his players didn’t end up at United, playing hardball for the likes of Gareth Bale, Luka Modric, Eric Dier, and Toby Alderweireld. Just this summer, United abandoned their pursuit of Harry Kane because they figured there was no point getting into a long, drawn-out back-and-forth with Levy, who would probably just squeeze every last drop out of them and then try to get even more.
When it came to loaning out left back Sergio Reguilón, though, Levy barely put up a fight. Heck, if reports are to be believed, Spurs aren’t even getting a loan fee and United can break the deal in January if they wish. United are covering his wages, but at £53,000 a week, he’s not even making as much as Brandon Williams was.
So what happened to Daniel Levy, master negotiator? Did he get played by United’s crack team of brilliant, forward-thinking innovators?
Or was he too busy doing a celebratory dance and high-fiving his fellow executives for getting a rival club to take a completely unwanted player off their hands and cover his wages? If anything, he was probably trying to make sure he didn’t do anything to blow the deal.
So, the fact that Daniel Levy did everything short of pack this guy’s bag for him means we’re getting hosed right?
How quickly things can change. Going into the 2020-21 season, Reguilón was very much a player in demand. Reguilón, who had spent the just-completed season playing on loan at Sevilla, was named best left back in La Liga and had helped his team win the Europa League.
In fact, United had been heavily linked to the Real Madrid left back, but reportedly balked at Madrid’s demand for a buyback clause.
Instead, it was Tottenham Hotspur that won the race, paying a fee of £27.5 million (potentially rising to £32 million) to acquire the talented Spaniard.
A big reason why the deal went through was because of then-manager Jose Mourinho. The Special One had kept tabs on his former youth team player, watching him during the 2018-19 season and praising him for his performances against Barcelona that season. “I say, from my perspective too, one of the players that could show that Real Madrid’s traditional desire to compete against Barcelona was a kid like Reguilón, who had a very good approach in both matches [against Barca],” Mourinho said at the time.
As such, Reguilón became an important player during his inaugural season at Tottenham. He made his league debut during Spurs’ 6-1 demolition of Manchester United and went on to start 36 out of 45 matches in all competitions, including 26 out of 31 in the league. Reguilón finished the 2020-21 season with 6 assists in all competitions— matching Luke Shaw’s total for that season.
He also earned a £500 leg of ham after Mourinho challenged him to keep Riyad Mahrez quiet and Reguilón did so, helping his club beat Manchester City 2-0 in November 2020.
However, his fortunes took a turn once Mourinho left. In the 2021-22 season, he started nine of 10 league matches under Nuno Espírito Santo before the former Wolves manager was sacked. New manager Antonio Conte played a completely different defensive system, utilizing three center halves in the back, so Reguilón had to make due with rotating with Ryan Sessegnon as left-sided wingbacks. The results were mixed, and Reguilón didn’t help his cause by missing time towards the end of the season with a groin injury.
The following season, Conte froze him out, leaving him off the preseason tour and making him available on the transfer market. Ultimately, Reguilón joined Atletico Madrid, where he only made 12 appearances all year before returning to North London in the summer.
This season, Reguilón has yet to make a single matchday squad as it’s clear new Spurs manager Ange Postecoglou has no use for him. He didn’t even make the bench for Spurs’ midweek defeat to Fulham in the League Cup — although that might have been to preserve his market value by making sure he didn’t get cup-tied (something Chelsea didn’t do with Marc Cucurella, reputedly ten Hag’s first choice).
So who’s to blame for Reguilón’s fall from grace? Is it his fault for not living up to his potential? Or does the fact that he’s had four permanent managers in three years have something to do with it?
It’s probably a bit of both. But what’s clear is that he’s still young and, with the right manager, could still make an impact.
Erik ten Hag clearly believes in him, so that should bode well for him. Based on this scouting report, he often takes up a position in the center of midfield to help build up attacks — something ten Hag likes to do with Shaw. He also has pace, which always comes in handy.
So what are his weaknesses? Well, defending for one. There’s a reason why Mourinho felt the need to challenge him to keep Mahrez in front of him. For a club that’s been as shaky at the back as United so far, Reguilón doesn’t exactly inspire confidence. Especially with Raphael Varane joining United’s injury list this week.
He’s also not a great crosser, which means opposing defenses will hardly be quaking in their boots at the sight of Reguilón and Aaron Wan-Bissaka coming at them (although the latter does have an assist from a cross this year).
Ultimately, Reguilón will probably just be a stopgap until Luke Shaw and/or Tyrell Malacia are healthy. Clearly, ten Hag wasn’t happy with the prospect of playing Diogo Dalot out of position on the left and didn’t think Alvaro Fernandez was ready to fill the void, so he went out and got an experienced, natural left back.
Here’s hoping Reguilón shows some of the form that once made him one of the most exciting prospects in Europe. Otherwise, we’ll have to cross our fingers and hope that Shaw comes back sooner, rather than later.
