Manchester United’s deadline-day loan of Sergio Reguilon is the club’s first straight dealing with Tottenham since 2008, when former manager Sir Alex Ferguson had problems with the north London club.
United were forced to enter the market in the last days as they sought a temporary solution at left-back. Erik ten Hag was left with Alvaro Fernandez as his sole natural left-back when Luke Shaw suffered a muscle injury.
Tyrell Malacia has also been ruled out, and Ten Hag started Diogo Dalot at left back against Nottingham Forest due to a lack of experience. The Dutchman had identified a number of loan candidates, including Marc Cucurella and Marcos Alonso, to approach in the final week of the transfer window.
United’s initial choice was Cucurella, but the club refused to accept Chelsea’s expectations. Instead, they contacted Tottenham Hotspur, and Reguilon’s season-long loan was finalised on Friday.
It’s been 15 years since the two teams last negotiated a move, with Ferguson and David Gill refusing to work with Tottenham because their approach to selling Dimitar Berbatov irritated them. United had been in talks with the Bulgarian all summer but were dissatisfied as Daniel Levy kept shifting the goalposts and raising his expectations.
Levy delayed negotiations until the deadline, forcing United to pay £30.75 million for the striker. Ferguson later decided not to pursue Luka Modric, characterizing conversations with Spurs owner Tom Hicks as “more painful than my hip replacement.”
“You can’t discuss both sides of the issue with Daniel,” stated the former Reds manager. “It’s about him and Tottenham, nothing else, which is a good thing for his club.”
In the 13 years since, United has shown an interest in a number of Tottenham players but has never pursued them. Christian Eriksen said that Louis van Gaal, Jose Mourinho, and Ole Gunnar Solskjaer all wanted him at Old Trafford in 2017, with Mourinho also interested in Eric Dier.
Reguilon’s approach was likely aided by the fact that he was surplus to needs at Tottenham, whilst Berbatov and the other targets were star players at the time.
