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How it took them 72 days, and six candidates, to make a hire

It took 72 days, thorough discussions with at least six different candidates and one strong fan backlash, but Tottenham Hotspur finally have themselves a new head coach.

Nuno Espirito Santo was appointed last Wednesday, receiving a two-year contract at the end of a protracted and frankly calamitous search that began with Jose Mourinho’s sacking on April 19.

Chairman Daniel Levy is widely regarded as one of the shrewdest football administrators around, building arguably the best stadium in the world while creating an environment in which Mauricio Pochettino led Spurs to four successive top-four finishes and the 2019 Champions League final. Yet Tottenham’s chaotic attempt to find someone to take them back to that level — and ultimately beyond — after Mourinho’s disappointing 17-month tenure, was a world apart from the typical business savvy with which the club usually operates.

It’s a consequence of bad timing, pursuing frustrating dead ends and a confused thinking arising from the appointment midway through the process of new managing director of football, Fabio Paratici, who was hired in the wake of Mourinho’s departure. Santo has a huge task in taking Tottenham forward, one undermined at least initially by the knowledge that he wasn’t even close to being first choice for the role.

Spurs have played down the strength of their interest in certain names linked with the post but there were overtures made to Hansi Flick, Pochettino, Antonio Conte, Paulo Fonseca and Gennaro Gattuso, amongst others. That’s not to say Santo cannot succeed, of course, but the circumstances that brought about his arrival are far from ideal.

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Additional reporting by Julien Laurens

Super League, Mourinho and bad timing around first four targets

In Nov. 2019, there were 10 hours and 59 minutes between official club announcements that Pochettino had been sacked and Mourinho would be his successor, but this was no 11th-hour appointment.

Levy did not want to remove Pochettino. The pair had their disagreements — particularly earlier that year, when Pochettino argued furiously for significant investment to improve the squad that lost 2-0 in the Champions League final to Liverpool — but their bond remained strong. However, the alarming downward spiral of results — Spurs picked up just 25 points from Pochettino’s final 24 games — had extended through most of 2019, masked largely by that remarkable run in Europe, and Levy recognised that perhaps the era had come to an end after five-and-a-half years.

Talks with Mourinho were swift and sources told ESPN that Pochettino was only axed once the Portuguese had given a clear indication he would take charge.

The situation in 2021 was very different. The players had grown frustrated by Mourinho’s conservative approach in matches, repetitive training sessions and the alienation of certain popular individuals including Dele Alli and Gareth Bale. Yet Levy wanted to wait until it had been determined which (if any) European competition Spurs would qualify for.

Levy was acutely aware of Mourinho’s reputation when making the hire. He accepted there would be a degree of tension inside the club — a marked departure from the unity Pochettino had fostered — but the pay-off would come from Mourinho’s track record of delivering trophies: 25 of them during his time at Porto, Chelsea, Inter Milan, Real Madrid and Manchester United, including two Champions League and two Europa Leagues, something his predecessor had failed to achieve.

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Then came the launch of the Super League, a new competition shattering the existing UEFA structure of which Spurs would be a founder member. Within 12 hours of the formal launch on April 18, Mourinho was sacked.

A theory given credence by more than one agent who has a long-standing relationship with Levy is that Mourinho was sacked when he was because European qualification was rendered irrelevant by the Super League announcement. Moreover, they could potentially have the pick of any manager not in charge of one of the breakaway 15 clubs. Why else would you do it at the start of a week that ended with Tottenham in an actual cup final, and the chance to end a 13-year wait for a trophy?

Of course, Manchester City were strong favourites to win the EFL Cup over Tottenham, but Mourinho’s remarkable form in showpiece occasions — 12 wins from 15 finals — would surely have given Spurs every chance of success. Yet Ryan Mason, a 29-year-old interim boss with no managerial experience and later dubbed “Ryan Mates-on,” given his fondness of picking players he knew, led the team out at Wembley and they were beaten 1-0, registering two shots in 90 minutes. The expected goals for that final was 0.06 vs. 3.63.

A further reason for parting with Mourinho before the EFL Cup final was that a potential successor with time-sensitive availability was already lined up.

Two days before Mourinho was sacked, on April 17, Flick announced he would be leaving Bayern Munich. Flick was widely expected to replace Joachim Low as manager of the Germany national team, as Low’s departure after Euro 2020 was already public knowledge. Sources have told ESPN that Spurs discussed the vacancy with Flick, but the 56-year-old was always considering the Germany job as his next step.

During this period, Spurs are believed to have sounded out three other candidates: RB Leipzig’s Julian Nagelsmann, Ajax’s Erik ten Hag and Leicester’s Brendan Rodgers. The quartet (including Flick) are of varying ages, but they all fit the profile of a progressive coach succeeding with attacking football. However, Nagelsmann was earmarked as Flick’s replacement at Bayern and quickly accepted the job. Ten Hag showed interest in leaving Ajax, but neither the manager nor Levy was truly sold on the other and he extended his deal at the Eredivisie side to firmly end any discussion.

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Meanwhile, Rodgers has a contract at Leicester City until 2025. Levy was reluctant to pay high compensation and with Rodgers unwilling to push for an exit, their search turned elsewhere. And to make things more difficult, the Super League project collapsed as quickly as it had been announced, meaning Spurs would be viewed by interested parties on their current turbulent state, not the moneymaking potential that the new frontier had offered.

“Flirting” with Pochettino, trying to win over Conte, the Fonseca/Gattuso mess

Despite the split in 2019, Pochettino’s connection with Tottenham remains strong and in a rare newspaper interview from December of that year — a month after the Argentine was sacked — Levy left the door open to a possible return for the 49-year-old. However, nobody thought it would come this soon. Pochettino only re-entered management in January, taking charge at Paris Saint-Germain, where he won the club’s 14th Coupe de France, but missed out on the Ligue 1 title to Lille and was knocked out of the Champions League at the semifinal stage by Manchester City.

One source describes Pochettino as “something of a flirt” in situations where he has admirers at other clubs.

While working at PSG, Pochettino was living in a Paris hotel with his family back in London. Often when back in England, he would grumble to former colleagues about various frustrations and, around May 27, Spurs did make contact to see whether those teething problems were painful enough to walk away. Yet sources have told ESPN that while speculation suggested Pochettino was agonising over his future, he was in fact in regular dialogue with PSG president Nasser Al-Khelaifi discussing transfer targets for next season.

PSG had the extra insurance of triggering a one-year extension to Pochettino’s contract, connecting him to the club until 2023, but in any case his focus on improving the team only served to reassure the club’s hierarchy that a move back to Spurs was not something he was prepared to try and push through. It is not a coincidence PSG have been one of the most pro-active teams this early in the market, closing a deal for Liverpool midifelder Georginio Wijnaldum on a free transfer, setting up the same for Real Madrid defender Sergio Ramos and AC Milan goalkeeper Gianluigi Donnarumma, while finalising a €70m move to sign Inter full-back Achraf Hakimi .

At the start of June, Levy turned to Conte. The former Chelsea boss was out of work, having left Inter Milan after securing the club’s first Serie A title since 2009-10, reportedly due to the club’s financial issues. As those talks began, the prolonged period without a manager led to internal conversations as to whether a wider restructuring of senior positions at Tottenham was desirable.

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Levy had adopted a director of football structure in the past with mixed results — Franco Baldini, Frank Arnesen and Damien Comolli have all held the role — and the idea of delegating some important football decisions appealed.

Paratici was an obvious, high-calibre candidate who was available after deciding to leave Juventus after 11 successful years, and who boasted impressive credentials including nine straight Serie A titles and five Italian Cups. Significantly, he could also provide support in Spurs’ manager search, and he even remained on good terms with Conte from their time together at Juventus. Conte is a combustible character who can be difficult to manage, but Paratici’s presence encouraged the 51-year-old that he could receive the support he craved and the freedom to operate in the manner he wished.

Confirmation of Paratici’s appointment as “Managing Director, Football” came on June 12. He was to start work officially on July 1, but inevitably had a say in discussions over the new head coach. However, by this time his involvement was formalised, talks with Conte had stalled.

The reason why these negotiations eventually collapsed differs depending on their role in it. Conte’s camp have suggested it was about money and refusal to match his wage demands or invest heavily in the squad; sources close to Spurs dismiss any notion of financial complications and instead insist there were differing visions over the club’s future direction.

This setback sent Spurs back to the drawing board, albeit with Paratici now part of the decision-making team. Around June 13 or 14, Paratici recommended Fonseca, overlooking the somewhat awkward fact they were about to speak to the man sacked by Roma to make way for Mourinho, who’d been deemed not good enough for Tottenham.

Sources have told ESPN that Fonseca held an initial virtual meeting with Levy from Rome. The pair were aligned on their vision of the club, with Levy stressing the need for Spurs to play attacking football and promote young players. A face-to-face meeting then took place between Fonseca and Paratici in Milan. Although talks were positive, the content of those conversations changed somewhat, with Paratici reportedly expressing their differing priorities. Nevertheless, a verbal agreement was struck and early on the morning of June 17, a draft contract arrived for Fonseca’s agent to examine for final remarks.

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Spurs were offering a two-year contract with an option for a third season and sources claim Fonseca was excited by the opportunity he was apparently about to be offered. A meeting was even scheduled to discuss his United Kingdom work permit. The issue of who would be on his coaching staff had not been discussed, but was not viewed by Fonseca as a barrier to any agreement.

However, later that day and out of nowhere, Fonseca received a call from Paratici stating the deal was off. No detailed explanation was given and sources said that Fonseca is unsure what happened to this day.

Paratici had become aware of Gattuso’s sudden departure from Fiorentina, possibly directly from Gattuso’s agent Jorge Mendes, just 22 days after agreeing to take over. Gattuso impressed in a meeting with Paratici, and Levy could see the logic of his appointment. Yet he did not anticipate fans voicing their fervent opposition to Gattuso’s arrival not because of his mixed managerial record, but because of past comments he’d made on racism, sexism and homophobia.

The Tottenham Hotspur’s Supporters Trust formally raised the opposition to the Italian as #NoToGattuso trended on Twitter. Levy retracted the deal, and Spurs were back to square one yet again.

Sevilla claimed they turned down an approach for their head coach, Julien Lopetegui, while Spurs considered another move for Ten Hag given how earlier talks were left open-ended.

But with preseason fast approaching, Paratici raised the prospect of Levy reconsidering Santo despite reservations about his conservative style, particularly near the end of his four-year tenure at Wolves. Paratici had previously been interested in taking Santo — another Mendes client — to Juventus during his time there and once Levy was persuaded of the benefits, talks progressed swiftly with a two-year contract agreed.

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With Harry Kane’s future a pressing priority and moves in the transfer window to get right, the hard work for Tottenham starts now. But what a journey they have been on just to get this far.

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