He might be sitting in the dugout of another Premier League club at the moment, but Mauricio Pochettino's time at Tottenham Hotspur still defines his career more than any other job he has since held.
He managed to get the Lilywhites regularly challenging for major honours, and one of the core reasons for that was some of the brilliant signings he made at the club.
However, as savvy as he was, Pochettino was still guilty of a few transfer clangers.
With that in mind, Football FanCast has turned the clocks back and created a list of Mauricio Pochettino's worst signings as Tottenham boss.
10 DeAndre Yedlin (£2.5m)
Right, so kicking off our list of the ten worst signings made in the Pochettino era is American full-back DeAndre Yedlin.
Now, some of you may wonder, 'When did Yedlin ever play for Tottenham?'
Which is our point exactly.
Before he was regularly turning out for Newcastle United, the Seattle-born player was, for a brief time anyway, a Tottenham player. He was actually just the fourth signing that Pochettino would make as Spurs boss, when the club paid a fee of around £2.5m to MLS side Seattle Sounders for his services in August 2014.
There was quite a bit of excitement around the youngster at the time, especially after he had just performed admirably at the 2014 World Cup, but he would ultimately last just a year in N17.
In all, the American international would make just one singular appearance for the club before he was sold to the Magpies a year later. The only reason he isn't any higher on this list is the fact that he cost very little in the grand scheme of things.
And hey, things have seemingly worked out for Yedlin as well, considering he is now lining up with Lionel Messi every week for Inter Miami.
9 Ryan Sessegnon (£25m)
You might have two reactions to this inclusion, either that it is too harsh or that you totally forgot that Ryan Sessegnon was still a Tottenham player, and we'd forgive you for the latter.
The rapid winger come wing-back has been a Spurs player for over four years now following his £25m move from Fulham in August 2019, and in that time, he has failed to really do anything if we're being brutally honest.
Granted, he did spend the 2020/21 season on loan with Bundesliga outfit 1899 Hoffenheim, but even in Germany, he was simply just okay. In the three seasons he has spent in north London, he has made just 38 Premier League appearances, scored just two league goals and provided two assists.
In his defence, he has suffered from a string of injuries in N17, which must make it hard to develop any sort of form. Still, even so, for £25m and four years in which to prove himself, he has not shown anywhere near enough for his move to be considered anything other than a flop.
Luckily for him, he is still just 23, so he has plenty of time to prove the doubters – like us – wrong.
8 Serge Aurier (£23m)
Spurs spent £23m to sign Serge Aurier from Paris Saint-Germain in 2017, which was quite a bit of money for a full-back at the time, and so there was a general expectation that he was going to be the man to take Tottenham's defence up a level.
In reality, he proved himself to be a liability both for his pretty abysmal defensive awareness and his absurd ability to lose his head over the smallest of things on a football pitch.
Now, this wouldn't have been such a problem for the club had they not sold the far better Kieran Trippier just two years after buying Aurier, meaning that the Ivorian had to play more.
He somehow made 110 appearances for Spurs across all competitions before his contract was terminated by mutual consent in September 2021.
While he certainly isn't the worst player on this list and has actually looked quite good for Nottingham Forest recently, he was a poor signing, especially for £23m.
7 Benjamin Stambouli (£5m)
Okay, so we have moved from the pretty bad transfers to the undeniably rubbish now, and first on that list is French midfielder Benjamin Stambouli.
The Lilywhites signed Stambouli from Ligue 1 side Montpellier in the summer of 2014 for a fee believed to be in the region of £5m, and there was some excitement around the deal; after all, he had been a part of a league-winning team just two years prior.
However, he would last just a single season in England, making 25 appearances across all competitions and scoring just a single goal. He somehow wrangled a move to PSG in 2015, but he also lasted a year there.
6 Federico Fazio (£8m)
Another of Pochettino's first signings makes it onto our list next, and boy, he really didn't have the best judgment during that first summer in charge, did he?
Federico Fazio joined the club from La Liga outfit Sevilla for a fee of around £8m and ultimately failed to make any sort of positive impact at the club.
He made just 20 Premier League appearances in north London and picked up one straight red, which was honestly the most notable thing he did in White.
The unfortunate thing for Spurs fans, though, is that when he was on loan at Roma, he was actually really quite good, and when the move was made permanent in 2017, he remained so.
Sometimes, a player and a team just don't mesh for whatever reason, and this was undoubtedly an example of that.
5 Georges-Kevin N'Koudou (£11m)
Now, if you thought £8m for 20 appearances was bad, wait til you hear about Georges-Kevin N'Koudou.
The club were on the lookout for offensive reinforcements in the summer of 2016, and so they opted to spend £11m on the relatively unproved, but still exciting, French winger, N'Koudou.
Flash forward three years, and he had just been sold to Besiktas for £5m after just 11 Premier League appearances no goals, and one assist to his name.
4 Clinton N'Jie (£12m)
In August 2015, Tottenham were in need of a new striker to replace the outgoing disaster that was Roberto Soldado, and instead of signing an experienced backup to Harry Kane, they opted to go down the unproven route, a decision that backfired massively.
They ended up paying Lyon £12m to sign their young forward Clinton N'Jie, and to say that he was a flop would be kind.
In his first season as a Spurs player, he would make just 14 appearances across all competitions, failing to score a single goal and providing just one assist.
He would be loaned to Marseille the following season and then sold to the French side in the summer.
3 Giovanni Lo Celso (£55m)
The first big-money signing on the list, and despite showing glimpses of genuine ability and form during his time in N17, it just hasn't worked out for Giovanni Lo Celso.
The Argentine arrived on loan at Spurs in the summer of 2019, but the loan fee combined with the payment to make it permanent in January 2020 cost the club around £55m.
What did Spurs get for that enormous fee? Well, honestly, not very much at all.
During his four years as a Tottenham player so far, Lo Celso has made a grand total of 56 Premier League appearances and 86 across all competitions. He has only scored eight goals and provided six assists in that time, and it's hard to see him improving that record once he returns from injury.
The only reason Lo Celso isn't higher up on this list is that there is a slight chance he could still turn things around, although, who are we kidding, he isn't going to, is he?
2 Vincent Janssen (£19m)
Coming in as the runner-up in this list is potentially one of the most disappointing striker signings in the league's history, not just for Spurs.
Signed from AZ Alkmaar in the summer of 2016 for around £19m, Vincent Janssen was supposed to be the perfect player to act as a backup, or even challenge, Harry Kane.
He had just come off a season in which he won the Eredivisie Golden Boot after scoring 27 league goals, so the expectation was that he would thrive in England.
That expectation ended up ever so slightly missing the mark.
Across his entire Tottenham career, Janssen made 42 appearances and scored just six goals. He was so bad that he was sent out on loan to Turkey in his second season, and when he flopped there, he was sold to Mexican side Monterrey in 2018.
While his fee wasn't massive, we can't think of many strikers who failed to live up to the hype quite as dramatically as Janssen.
1 Tanguy Ndombele (£63m)
Here we are then, the worst signing that Mauricio Pochettino made as the manager of Tottenham Hotspur, and it is quite the corker.
Tottenham were in a spending mood in the summer of 2019, and alongside signing Lo Celso, they also smashed their transfer record to bits by signing Lyon midfielder Tanguy Ndombele for an eye-watering fee of £63m.
There was a lot of excitement around this deal; after all, the Frenchman was a wanted man at the time and had been one of the very best players in Ligue 1 for a couple of years, so there was an expectation that he would flourish under Pochettino.
Unfortunately for the Spurs faithful, he did not flourish and instead regressed into a shell of the player he once was, making a grand total of 91 appearances for the club.
He has spent most of his time as a Spurs player either on the bench, injured or on loan to other clubs, and has seemingly fallen out of favour with every manager he has played under at the club.
There was some hope that Ange Postecoglou could revive his career, but the fact that he was sent on loan to Galatasaray in the summer has since quashed that hope.
Yes, he is still a Spurs player, so he could technically turn this all around, but come on, there is very little hope that he will ever come good.
Ultimately, he is the worst transfer that Pochettino made as Spurs boss.
