After 72 days of discussions with at least six candidates, and one fan backlash, Tottenham Hotspur finally has a new head coach.Nuno Espirito Santato was appointed last Wednesday. He received a two year contract after a long and difficult search that began with Jose Mourinho being fired on April 19.The chairman of Tottenham, Daniel Levy, is widely regarded as one the most intelligent football managers around. He built the stadium that's arguably the best in the world and created an environment where Mauricio Pochettino was able to lead Spurs to four consecutive top-four finishes. But Tottenham's chaotic search for someone to lead them back to that level, and eventually beyond, after Mourinho's 17-month disappointing tenure was an extraordinary departure from the usual business acumen with which the club operates.It is a result of poor timing, following frustrating dead ends, and confused thinking. The appointment of Fabio Paratici as new managing director of football was made midway through the process. Paratici was appointed in the wake Mourinho's departure. It is a daunting task for Santo to take Tottenham forward. He was not even close to being the first choice.Spurs declined to express interest in certain names, but overtures were made to Hansi Flick and Pochettino as well as Antonio Conte, Gennaro Gattiso, Paulo Fonseca, Pochettino, Antonio Conte and Antonio Conte. Santo's arrival was not inevitable, however, the circumstances surrounding it are not ideal.Julien Laurens also contributed additional reportingSuper League, Mourinho, and poor timing around the first four goalsThere were 10 hours and 59 mins between official club announcements that Pochettino was resigned and Mourinho would take his place, but this wasn't an 11th-hour appointment.Levy didn't want Pochettino to be removed. Although they had some disagreements, especially in that year's Champions League final loss to Liverpool, Pochettino was determined to invest heavily in his squad. However, their relationship remained strong. The alarming downward trend in results, Spurs picking up only 25 points in Pochettino’s 24 final games, continued through 2019, but was largely masked by the remarkable run to Europe. Levy recognized that maybe the era was over after five-and a half years.Mourinho was in quick talks with Mourinho. Sources told ESPN that Pochettino was only fired after the Portuguese gave clear indications that he would be taking charge.In 2021, the situation was quite different. Mourinho's strict approach to matches, repetitive training sessions, and alienation of some popular players like Dele Alli or Gareth Bale had caused frustration among the players. Levy was determined to wait until the European competition Spurs would qualify for, if any.Levy was aware of Mourinho’s reputation before he hired him. Mourinho knew there would be tension within the club, a departure from the unity Pochettino fostered. But the payoff would come from Mourinho’s track record of delivering trophys: 25 during his time at Porto and Chelsea, Inter Milan and Real Madrid, as well as two Champions Leagues and two Europa Leagues. This was something that his predecessor failed to do.The Super League was launched, a new competition that shattered the existing UEFA structure in which Spurs were a founding member. Mourinho was fired within 12 hours of the official launch on April 18.After a long and chaotic search, Nuno Espirito Sante was finally confirmed as Tottenham boss. Tottenham Hotspur FC/Tottenham Hotspur FC via Getty ImagesOne agent with a long-standing relationship to Levy suggests that Mourinho was fired because European qualification was made irrelevant by the Super League announcement. They could also have the chance to pick any manager who is not the head of one of the 15 breakaway clubs. It's a great way to start a week that saw Tottenham win the cup final and end the 13-year wait for a trophy.Manchester City was the clear favourite to win the EFL Cup, but Spurs would have been able to capitalize on Mourinho's extraordinary form in showpiece events -- 12 wins from 15 finals - if they had Mourinho. Ryan Mason, a 29 year-old interim manager with no managerial experience, took the team to Wembley. He scored two goals in 90 minutes and led them to defeat. It was expected that the final would see 0.06 goals against 3.63.Another reason Mourinho parted ways with him before the EFL Cup finals was that a possible successor was already in place with a time-sensitive availability.Flick, two days after Mourinho's resignation, announced that he was leaving Bayern Munich. Flick was widely expected as the manager of Germany's national team. Low's departure was known. ESPN has been told by sources that Spurs discussed the vacant position with Flick but that the 56-year old was always thinking about the Germany job.Spurs were believed to have sounded three more candidates during this period: RB Leipzig's Julian Nagelsmann and Ajax's Erik ten Ha, as well as Leicester's Brendan Rodgers. Flick is among the quartet, although they are all of different ages. However, they all match the profile of a progressive coach who excels at attacking football. Nagelsmann, however, was quickly offered the position of Flick's replacement at Bayern. Ten Hag expressed interest in leaving Ajax but neither Levy nor the manager were sold. He extended his contract at the Eredivisie side to end all discussion.Rodgers still has a contract in Leicester City for 2025. Rodgers refused to negotiate for an exit and Levy hesitated to pay a high amount of compensation. To make matters worse, Super League collapsed just as soon as it was announced. This meant that interested parties would only be able to view Spurs based on their current state and not the potential for moneymaking.Spurs boss Levy was uncertain of the right person to replace Jose Mourinho. He eventually hired a director for football to help him. Jon Bromley/ MI News/NurPhoto via Getty Images"Flirting” with Pochettino to win over Conte and the Fonseca/Gattuso messDespite the 2019 split, Pochettino still has a strong connection to Tottenham. In a rare interview with the newspaper from December 2018, a month after the Argentine's departure, Levy suggested that Pochettino could return to Tottenham. It was unexpected, however. Pochettino was only able to re-enter management at Paris Saint-Germain in January. He won the 14th Coupe de France. However, he missed the Ligue 1 title to Lille. Manchester City knocked him out of the Champions League semifinals.According to one source, Pochettino is "something of an flirt" when he meets admirers from other clubs.Pochettino lived in Paris with his family while he was working for PSG. Pochettino would often complain to his former colleagues back in England about various frustrations. Spurs made contact with him around May 27 to find out if those teething issues were enough to make him leave. ESPN has learned that sources claim that Pochettino was not worried about his future and was actually in constant dialogue with Nasser Al-Khelaifi, the president of PSG, discussing next season's transfer targets.PSG was able to trigger a one year extension to Pochettino’s contract. This connected him to the club until 2023. However, his focus on improving team performance only served to reassure club hierarchy that a return to Spurs was not something that he was willing to push through. PSG has been one of the market's most proactive teams. They closed a deal with Liverpool midifelder Georginio Wijaldum on a transfer for free, and set up the same for Sergio Ramos, AC Milan goalkeeper Gianluigi Donarumma, and completed a 70m deal to sign Inter fullback Achraf Hakimi.Levy switched to Conte at the beginning of June. After securing Inter Milan's first Serie A title in 2009-10, Levy, the former Chelsea boss, was out of work. This may have been due to financial problems at the club. The long absence of a manager caused internal discussions about whether it was possible to restructure senior positions at Tottenham.Levy had previously appointed a director for football in the past. Frank Arnesen, Damien Comolli and Franco Baldini all served this role. The idea of delegating important football decisions appealed to Levy.Paratici immediately started to assist in the search for a new manager. Filippo Alfero – Juventus FC/Juventus FC via Getty ImagesParatici, a high-calibre candidate, was readily available after he decided to leave Juventus. He had 11 years of success and boasted impressive credentials, including nine straight Serie A titles, five Italian Cups, and nine consecutive Serie A titles. Paratici could be a support for Spurs' manager search and even maintained good relations with Conte during their time at Juventus. Although Conte can be a volatile character and can be difficult to manage at times, Paratici's presence helped the 51-year old to feel that he could get the support and freedom he desired.Paratici was confirmed as the "Managing Director, Football" on June 12. Paratici was due to officially start on July 1 but had an input in the discussions about the new head coach. Talks with Conte were already stalled by the time he was officially involved.Depending on who was involved, the reason these negotiations ended in a stalemate will vary. Conte's camp has suggested that it was money. He refused to pay his wage demands and he did not invest in the squad. Sources close to Spurs deny any financial complications. They insist that there were different visions about the club's future.Spurs were forced to rethink their plans after this setback, with Paratici still part of the decision-making group. Paratici suggested Fonseca around June 13-14, ignoring the awkward fact that they were about to talk to Roma's man who was sacked to make room for Mourinho, who had been deemed unfit for Tottenham.ESPN has been informed by sources that Fonseca met with Levy in Rome for an initial virtual meeting. They shared a common vision for the club. Levy stressed the importance of Spurs playing attacking football and promoting young players. Fonseca met Paratici in Milan. The talks were positive but the content of the conversations was not as good. Paratici apparently expressed their divergent priorities. However, a verbal agreement was reached and early in the morning of June 17th, a draft contract was delivered to Fonseca's agent for final comments.Play 0:56 Gab and Juls say Nuno Espito Santo to Spurs makes absolutely no sense Gab Marcotti, Julien Laurens, and Julien Laurens ask about Nuno Espirito Sante's chances at success at Tottenham.Spurs offered a two-year contract with an optional third season. Sources claim Fonseca was thrilled at the chance he was about to be given. Even a meeting was scheduled to discuss Fonseca's United Kingdom work permit. Fonseca did not consider the issue of his coaching staff a problem, but it was not discussed.Paratici called Fonseca later that day to inform him of the cancellation. Fonseca was not given any explanation and sources say that he is still unsure of what happened.Paratici was made aware by Gattuso's abrupt departure from Fiorentina 22 days after he had agreed to assume the role. Paratici was impressed by Gattuso's performance in a meeting, and Levy could clearly see the logic behind his appointment. He didn't anticipate that fans would be so hostile to Gattuso’s arrival, not due to his mixed managerial history, but because of previous comments he made about racism, sexism, and homophobia.Tottenham Hotspur's Supporters Trust officially raised opposition to the Italian, as #NoToGattuso became a trending topic on Twitter. Spurs were back at square one after Levy pulled out of the deal.Sevilla claimed that they declined an approach from Julien Lopetegui as their head coach. Spurs, however, considered another move to Ten Hag considering the fact that earlier talks had been left open.Paratici brought up the possibility of Levy considering Santo, despite his reservations about his conservative style. This was especially true as he neared the end of his four year tenure at Wolves. Paratici had been interested in Santo, another Mendes client, to Juventus during his time there. Once Levy was convinced of the benefits, negotiations moved quickly to a two year contract.Tottenham must now get to work. Harry Kane's future is a priority. It has been a long journey, but they are now at the top of their game.