Tottenham Hotspur have spent big in their pursuit of a return to the top, and saw it finally come to fruition under the careful guidance of Mauricio Pochettino.
Joining from Southampton, the tactician quickly went about cultivating not just a squad but an atmosphere worthy of a club their size, helping to usher in a refreshing regime that not only would see them thrive, but also help players feel comfortable enough to play their best football free from burden.
As such, the likes of Toby Alderweireld, Heung-min Son, Harry Kane and Dele Alli were all transformed into some of the Premier League's finest in their roles, whilst even Jan Vertonghen and Christian Eriksen, who were left over from the previous management, were integrated too.
All the years of preparation finally seemed to be geared towards earning that elusive silverware until, spurred on by their failure in the Champions League final and inability to capitalise on the weakness of the division when Leicester City secured the title, Daniel Levy changed directions.
The appointments of Jose Mourinho and Antonio Conte outlined a vast shift in the club's mindset, abandoning steady progression in favour of winning now. However, in brushing aside the journey, when the end result fell short, they were left with little to go back on.
Ange Postecoglou's entrance notes a return to what they know, as they seek to expunge those failures of the past in order to enjoy a brighter future.
Who is Spurs' worst-ever signing?
During that stint, and indeed whilst Pochettino was in charge, there were some true transfer howlers as additional money began being pumped into the game.
The 2017 sale of Neymar to Paris Saint-Germain completely altered the landscape of the transfer market, and since then, anything has become possible.
Selling clubs can seemingly command any fee, with Declan Rice's £105m move, and Moises Caicedo's £115m switch just weeks later, startling proof of this.
Whilst Spurs are yet to be so brazen with their funds, the likes of Tanguy Ndombele, Davinson Sanchez and Moussa Sissoko are all examples of a huge expenditure that offered very little return across their respective periods in N17.
Although his actual transfer fee might not have been as lofty as any of that aforementioned trio, that does not excuse the car crash of an acquisition that Sergio Reguilon was, and still proves to be, with the Spaniard still on Levy's books.
Joining from Real Madrid under Mourinho's ill-fated tenure, the 26-year-old came with an impressive pedigree, expected to offer huge experience down that left flank alongside an injection of dynamism to benefit both ends of the pitch.
After all, in a recent loan spell with Sevilla before moving to England, the 5 foot 8 flop was named the best left-back in La Liga.
However, what they actually received was a nervous defender lacking in confidence, and seemingly incapable of retaining defensive shape or winning a 1-on-1 duel. As such, he was lambasted as recently as 2022 by pundit John Wenham: "He’s so average it’s untrue. I always go back to these constant rumours about Barcelona or Real Madrid being interested in him. There’s always stuff about them paying a premium for him, it’s nonsense.
"He’s just not that good. For me, he is the worst of the bunch."
Having since made 67 senior appearances, it should come as no surprise that Postecoglou was willing to sanction his swift exit in the summer, with the left-back moving on loan to Manchester United.
After all, his debut year in England saw him struggle, losing possession 16.1 times per game whilst being dribbled past 0.9 times per game, and only providing a disappointing 0.6 key passes per game too, via Sofascore.
Little altered as he remained at the club, as his chaotic and somewhat thoughtless presence at full-back was typified through his ridiculous own goal against Aston Villa in May 2021, as he needlessly swung at a clearance under no pressure, only to see the ball slice off his boot and beat Hugo Lloris in goal.
Offering little composure or offensive impetus, it should come as no surprise that he has since been banished.
How much did Spurs pay for Sergio Reguilon?
What makes the deal so disappointing, other than the fact that his woeful form has seen fans' expectations shattered given they were taking a young star from the Spanish giants, is the financial side of it.
Per Game
£559k
Per Minute
£7400
Per Goal
£18.75m
Per Assist
£4.1m
Per Yellow Card
£3.4m
After all, they were forced to unload a mouth-watering £32m to secure his services, in a deal that was somewhat overshadowed by the loan return of Gareth Bale.
This would perhaps explain the lack of uproar surrounding such foolish spending, which is made all the more laughable given Los Blancos inserted a buy-back clause into the deal, suggesting that they obviously had some faith that he could flourish.
What is Sergio Reguilon's salary at Spurs?
Whilst with big acquisitions an equally large salary usually follows, Reguilon strangely bucked the trend, likely due to the negotiations of the ever-frugal Levy.
As a youngster yet to truly prove his quality at a consistently elite level, a £53k-per-week deal made perfect sense, allowing for plenty of scope for improvement should he fulfil his potential.
However, that has obviously failed to occur, and it is now the Red Devils who are being forced to unload that figure as he sees out his season-long loan at Old Trafford.
Amid his failure to make Erik ten Hag's struggling and threadbare first team due to injury, his parent club are shining, although they have already forked out £5.5m on his wages previously.
Does Sergio Reguilon deserve to earn £53k-per-week?
It's certainly fair to say that Reguilon has done little to merit either his wage or transfer fee, given the lack of positive input offered.
After all, he was acquired by Mourinho in an effort to usher in a prosperous, trophy-laden era for a club, and obviously failed in that venture given they are still going 15 years and counting without tasting silverware.
To combine the initial money spent to tempt him from Madrid with the two full years he has actually spent playing for the Lilywhites, and the defender has actually snagged a frustrating £37.5m from Levy's pocket.
A truly woeful piece of business that arguably typifies a period completely devoid of any long-term strategy.
