Roberto De Zerbi declared what he expected from this summer transfer window in the moments after he and his Tottenham players had kept the club in the Premier League.
“From tonight we have to start to build a new team. I don’t think we have to change too many players,” he said on May 24. “We have 10, 11, 12 players good enough to stay and then we have to complete the squad with the top level of players.”
In the end Spurs changed many players. De Zerbi was handed 10 new signings in the window – every one of them with Premier League experience – while seven big names departed from his first team and there were loans and transfers galore from around the fringes of the squad.
In all a whopping 54 ins and outs took place across De Zerbi’s first team squad and Wayne Burnett’s U21s during the summer with the doors at Hotspur Way constantly revolving.
The north London outfit committed £394million to De Zerbi’s new recruits and that could eventually reach £469million, with the option to add another £75million next summer with on-loan Ukrainian winger Mykhailo Mudryk, the ninth arrival of the club’s window.
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It was also a summer in which Tottenham learned how to sell properly, or at least in bulk, and they could recoup a potential £264million from the outgoing deals agreed, helping them with the profit and sustainability rules.
De Zerbi already knew what he wanted this summer back in March, during his early discussions with Spurs’ sporting director Johan Lange and CEO Vinai Venkatesham as well as the club owners, the Lewis family. The Italian made it clear that if he saved them all from relegation then major improvements were required and he met an organisation more than willing to change after decades of doing things the same way, a way which had not produced results on the pitch.
The new regime had promised actions not words and they needed to deliver. Tottenham moved quickly and decisively in the transfer market in the early weeks, the recruitment staff and De Zerbi putting off their post-season holidays until things were in motion.
With De Zerbi’s ideas at its core and his player profiles clear to fit his brand of football, Spurs’ summer recruitment was led by the three-pronged team of Lange, Venkatesham and new director of football operations Rafi Moersen.
Those who know Lange and dealt with him in recent months say the Dane appeared happier and unshackled this summer. The club’s improved wage structure and the backing of owners Vivienne Lewis and her son-in-law Nick Beucher enabled him to move for the targets at the top of his recruitment list rather than battling for bargains in the tiers below.
De Zerbi would later praise the sporting director for the “solutions” he would come up with to get some of the deals over the line during a hectic window. Venkatesham had previously admitted he would be looking to bring in another sporting director-type to fill the gap left by Fabio Paratici alongside Lange after the window to share the load, most sides now operating with two people in those positions in the modern game and many of them with long notice periods.
This summer the trio at the top utilised their contacts at clubs across the Premier League, working to their different strengths. Venkatesham leaned on his relationships at West Ham and Newcastle among others to get some huge transfers done and Moersen would prove instrumental in the club’s big double deal with his former employers Manchester City.
De Zerbi was more than happy with the already-begun discussions over free transfers for Andy Robertson and Marcos Senesi, well aware that they would suit his brand of football and agreeing with Lange on placing importance in adding more leaders into the club.
With captain Cristian Romero and goalkeeper Guglielmo Vicario having told De Zerbi in their first meeting with him that they both wanted to leave the club, he set about preparing for their exits. Antonin Kinsky had already proved his worth and the head coach informed the young Czech stopper that he would become his new number one between the sticks with a new contract swiftly following.
De Zerbi was keen to reunite with his Brighton centre-back Jan Paul van Hecke, another leader who played similar line-splitting passes as Romero. Others were interested in the Dutchman but he made it clear that he wanted the reunion just as much and during the World Cup Tottenham eventually paid exactly what the Seagulls wanted – £52million for a player in the final year of his contract.
It set the precedent for a summer in which Tottenham just tried to make things happen rather than hope they might.
De Zerbi wanted a new dynamic midfield engine room and Spurs smashed their transfer record twice to give the 47-year-old his two top choices – first £85million for Mateus Fernandes from West Ham and then £92.5million + £7.5million in add-ons for Newcastle’s Sandro Tonali.
The Lilywhites saw off competition from Manchester United to sign Fernandes and the Portuguese is the player probably causing the most excitement behind the scenes at the club, with the recruitment department believing they have signed a midfielder who will soon be among the game’s best.
In Tonali, Spurs could have their first £100million signing if the 26-year-old unlocks all the add-ons and they saw off Manchester City to bring in the Italian. De Zerbi played his part in convincing all of the new faces to join him over the competition and his previous relationships with both Van Hecke and Tonali helped, having met up frequently over the years with the latter in the northern Italian city they both loved – Brescia.
When the deal was finally sealed for Tonali, Venkatesham rang De Zerbi with a video call, the CEO telling his head coach the news with the biggest grin.
De Zerbi was a constant presence in negotiations with players, talking to their agents and occasionally leaning on his own long-standing relationships.
He texted Van Hecke an expletive-filled message after that final game of the season against Everton, telling him he had to sign after playing his part in trying to get the club relegated with his last-gasp assist for Georginio Rutter’s equaliser at the Tottenham Hotspur Stadium the previous month.
With experienced goalkeeper Martin Dubravka also brought through the doors, De Zerbi had six signings in place as he started to get to work with his players in his first pre-season at Hotspur Way. That was unheard of at the club and a sure sign that he was getting his way.
Savio celebrates what would ultimately be Ben Davies’ goal during the Carabao Cup second round match between Tottenham Hotspur and Charlton Athletic
Even though he rarely has much of it, De Zerbi knew that patience would be required for his attacking signings as he was confident they would arrive. The Italian was so sure he would get Savio eventually that he began to plan for life with the young winger, discussing with his staff on the tour to New Zealand and Australia how he would best utilise the 22-year-old and turn him into a star.
The Brazilian agreed that the Spurs boss was perfect for him and set his heart on the move, even if he knew City were not desperate to let him go and would need a replacement first. He immediately told new coach Enzo Maresca that he wanted to head to north London in the hope of getting the ball rolling.
Tottenham had struggled before to get the Manchester side to allow Savio to leave, trying in two previous transfer windows and it was not until August 25 when they finally got their man with a £75million bid that could rise by another £10million with add-ons. The price tag surprised many, but it reflected just how good City believe the winger will become when he adds the end product to his remarkable dribbling ability.
De Zerbi had another passion project though he wanted from City in Omar Marmoush. The 27-year-old had starred at Eintracht Frankfurt and in his first half-season at the Etihad Stadium. The Egyptian then spent a season stuck in the shadow of Erling Haaland but De Zerbi was certain that the explosive attacker could be a big player within his system, adding more pace to Savio’s and bringing the pressing game that was vital to his attack.
A loan deal was agreed with an easily achievable obligation to buy Marmoush for £50million with another £10million in add-ons, making it a potential £145million double swoop on the Manchester club.
That money had to be balanced out through sales and De Zerbi made it clear that if players wanted to leave his project then they could go, apart from one player, Lucas Bergvall. The Spurs head coach believes the Swede can become a star if developed properly and the player eventually softened his desire to leave, simply wishing to be trained as a number eight after a mess of a previous season under Thomas Frank and Igor Tudor.
Approaches were turned away for the 20-year-old but others departed. Djed Spence asked to leave as he knew Pedro Porro would always be first choice ahead of him and Spurs sold both the England full-back and Romero within a couple of days to Inter and Atletico Madrid respectively.
Pape Matar Sarr wanted to go and eventually went on to Juventus on a £2.4million loan with obligation to buy for £23.5million. That all three departed for around the £30million mark showed the chasm between what the Premier League will spend and the rest of Europe, hence why so many English clubs looked to sell to each other this summer.
Tottenham’s fourth biggest sale in their history came with the departure of Luka Vuskovic, a talented 19-year-old centre-back who had never played in the Premier League but went to Brighton for a £50million package. The Croatian made it clear that he did not want to go out on loan again and uncertainty over his lack of pace for the English game led to Spurs eventually cashing in their chips and accepting the Seagulls’ bid. Time will tell whether it was a grave error or the right choice.
The most problematic of those who asked De Zerbi to leave was probably Kevin Danso. Most inside the club thought the Austrian would accept his role as a squad player but when he was not named in the starting line-up for the Carabao Cup game against Charlton, and Sunderland came knocking, the popular defender asked to be allowed to make the move.
Spurs rejected the initial loan move but would later agree a £2.5million temporary deal on deadline day only because it came with an obligation for Sunderland to buy Danso for £22.5million if they stay up. The problem was that it continued a flood of right-sided centre-backs leaving the club.
Romero, Vuskovic and Danso had all gone. Radu Dragusin also left for Fiorentina on loan with a £21.4million obligation to buy with even Ashley Phillips leaving for Middlesbrough in a £20million package and Kota Takai sealing a loan to Japanese-owned Belgian side Sint-Truidense VV.
That left Van Hecke as the only senior centre-back able to play on the right side of defence. Spurs began looking for what was a difficult profile of player, a homegrown defender to replace Danso in that category of the squad list but also one who would accept that they would have a fight on their hands to displace De Zerbi’s main man in Van Hecke.
Tottenham signed Tosin Adarabioyo from Chelsea on transfer deadline day(Image: Brendon Thorne/Getty Images)
Spurs had long kept an eye on Tosin Adarabioyo, trying to get him during his Fulham days and then when he became a free agent, only for him to choose Chelsea as he feared being unable to get past Van de Ven and Romero back then.
Now felt like the right time for both parties and a loan deal was discussed for the 28-year-old, one of the best friends of Spurs striker Dominic Solanke. That would soon have to be shelved though for a different kind of deal.
That’s because of Tottenham’s pursuit for one more attacker to bolster De Zerbi’s squad. It would be a chase in which Manchester City would switch from friend to foe.
Spurs had beaten the Citizens to signing Tonali earlier in the window but then handed them the £145million for Savio and Marmoush that would end up arming the Manchester side with the money to cause the north Londoners all kinds of problems.
Junior Kroupi was a big target for Spurs but Bournemouth’s reluctance to sell and eventually the Frenchman’s injury scuppered any chance of him moving to the capital.
De Zerbi had Liverpool’s Cody Gakpo high up on his attacking wishlist and Tottenham looked to make that a reality. Andoni Iraola was not that keen on letting the Dutchman go and especially not without a replacement. Time ticked on and while everyone waited, City made the decision to go for the 27-year-old themselves and his head was turned.
Frustrated but not done, Spurs turned to another on their list in Everton’s Iliman Ndiaye, a different kind of winger but one who could also play as a number 10 through the middle. They started to progress with talks with the Toffees only for City to find themselves running into the same quicksand as Tottenham did with Gakpo, Liverpool just not in the position to sell him.
So the Lilywhites could only watch on in horror as City once again turned to their target and took Ndiaye off the table. After a summer spent upsetting the traditional big boys with big fees and increased wages, Spurs found themselves back in their place in the transfer food chain.
That meant Tottenham had to drop further down their wishlist, De Zerbi maintaining that Plan Bs or Cs are not lesser players, simply different players. However, it was a blow to the club, who had managed to secure all of their top targets until those 72 hours or so from hell.
What came next was all the proof needed that the Italian holds the power at Spurs after saving them from a costly £250million relegation. In their discussions with Chelsea over Adarabioyo, the club enquired about De Zerbi’s former Shakhtar starlet Mudryk. As with the move for Adarabioyo, it felt like a panic move at the end of an otherwise well planned and patient window.
Mudryk has not kicked a ball in anger in a competitive match for almost two years due to a recently-ended doping ban for an “adverse finding” for banned substance meldonium. The Ukrainian contested the suspension throughout and appealed with the Court of Arbitration for Sport.
He is a player De Zerbi knows well – he calls him “Misha” – and once declared would be a future Ballon D’or winner before he struggled to impress at Chelsea. Mudryk was a superstar in the making at Shakhtar under the Italian, who used him off the left to great effect, not only domestically but also in the Champions League after he had transformed his young winger’s habits off the pitch and on the training ground.
Spurs and De Zerbi decided that if – and it’s a very big if – they can get him firing again then he could end up being a sleeper hit of this summer. Mudryk calls the Tottenham boss his “footballing father” so they were always going to be the top choice for the player once they entered the fray.
To negate the risk of taking on a player just returning to football, it had to be a loan move and that ruled out such a deal for Adarabioyo, as a Premier League side cannot loan two players from another side in the division.
A permanent deal for the centre-back was negotiated instead which will cost Spurs £10million with another £2million in add-ons and made him the first player to move permanently between the two clubs since Carlo Cudicini in 2009.
So Mudryk could now be loaned but also Tottenham did not want to simply help Chelsea reinvigorate their £61million signing from 2023 out of the kindness of their heart. An option to buy him next summer had to be negotiated and that the figure would end up being £75million was testament to the fact that Chelsea remain wary he could indeed spark to life with the right coaching.
Mykhailo Mudryk has joined Tottenham Hotspur on loan from Chelsea(Image: Courtesy of Tottenham Hotspur)
Either way, if Mudryk tanks at Tottenham then they do not need to keep him and if the Ukrainian becomes a star again under De Zerbi’s tutelage then the fee will become worth it in today’s swollen Premier League market if Spurs do not look to haggle it down.
So De Zerbi got his ninth and 10th signings of the summer to complete a remarkable transfer window that has strengthened Spurs in most positions apart from that diluted right-sided centre-back area and at right-back, where young midfielder Archie Gray will need to continue to deputise despite his displeasure at playing in the role. Tottenham rejected a number of approaches for the 20-year-old, slapping a not for sale or loan sign on him that stuck throughout the summer.
Two problems remain for De Zerbi. One is Richarlison, who refused to be sold to Everton if it was not on his terms, posting an unhappy monologue on social media about the situation after a summer in which his head coach said he constantly asked to leave the club.
Spurs have one too many foreign players to register in their Premier League squad and De Zerbi will have to decide between the Brazilian striker, who will be behind Marmoush and Solanke in the pecking order, and Xavi Simons, who is determined to be back far earlier than many expect from his ACL injury.
With the Saudi and Turkish transfer windows remaining open, all eyes will be on what comes next for Richarlison if he is told he will not be registered in De Zerbi’s squad. Danny Rose once sat out an entire season with his contract at the club in such circumstances but can the 29-year-old afford to do that at this stage of his career?
The other issue for Tottenham is the lack of a pathway for the younger players. Vuskovic departed, as did talented young striker Will Lankshear to Middlesbrough in a £20million deal and Alfie Devine to Preston for just £6million, while 19-year-old Mikey Moore was shipped off to Koln on loan and left-back Souza to Porto.
Teenager Tynan Thompson left for Manchester United for £4million plus £4million in add-ons amid a tough year in his personal life, coupled with never really getting a first team look-in.
The final transfer of Spurs’ window and the only player who required a deal sheet submitted to the Premier League before the 11pm deadline was Dane Scarlett. If anyone showcases the club’s pathway problems it’s the young striker. At 16, he was heralded by Jose Mourinho and then Antonio Conte as being one of the great hopes of English football.
Yet it never happened for Scarlett, sent out on four different loans by Tottenham, and on Tuesday his time at the club came to a close at the age of 22 with a permanent move to League One side Leyton Orient.
The hope for Tottenham’s future lies now with 17-year-olds Luca Williams-Barnett and Jun’ai Byfield, and 18-year-old defender Malachi Hardy among others, but it’s difficult to see how they will breakthrough in a squad now packed with senior stars in most positions and so few fixtures to come in a season without European football.
For years Spurs have always looked to the future and struggled to compete in the present. Now De Zerbi is leading a charge that will take them to the other end of the scale.
The money has been spent and until the window’s final days, everything the club went after, they got in an unprecedented summer of recruitment. Now it’s over to De Zerbi to work his magic with the strongest squad a Spurs manager has had for a purely domestic campaign in decades.
It’s not perfect but it’s a Tottenham Hotspur now packed with pace, skill and leaders and after years of Frankenstein’s monsters of squads compiled for a string of ever-changing managers, it’s one that suits the Italian’s brand of football more than he could have possibly imagined when he first joined.
De Zerbi has admitted that this transfer window has been beyond his wildest expectations and now after those opening two Premier League defeats he needs to get everything back on track, gelled together and moving in the right direction.
The knives are out for the club for daring to spend like the big boys and the narrative is already being shaped by the critics. The old Spurs would have crumbled. De Zerbi must ensure his new-look Tottenham Hotspur instead write their own story.
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