[19] Due to his tactical knowledge, charismatic and controversial personality, and a reputation for prioritising results over attractive football, he has drawn comparisons, by both admirers and critics, with Argentine manager Helenio Herrera.

The Carnation Revolution leading to the fall of António de Oliveira Salazar's Estado Novo regime in April 1974 also led to the family losing all but a single property in nearby Palmela.

[26] When his father returned to Rio Ave, Mourinho did not go with him and continued to play in the lower levels of the Portuguese football league system, first with Sesimbra, and then for Comércio e Indústria, where he finished his career.

[33][34][35][36][37] Mourinho dropped out of business school on his first day, deciding he would rather focus on sport, and chose to attend the Instituto Superior de Educação Física (ISEF) to study physical education.

[25][38] After 1989, the Higher Institute of Physical Education (ISEF) became the Faculdade de Motricidade Humana (FMH), or Faculty of Human Kinetics, in English, and since then it has been a part of the Technical University of Lisbon that would award a honoris causa doctorate degree to Mourinho in 2009.

[24] After leaving his job as a physical education school teacher,[42][43] Mourinho looked for a path into professional football management in his hometown and became youth team coach at Vitória de Setúbal in the early 1990s.

[41] The Porto team, consisting of players like Ljubinko Drulović, Domingos, Rui Barros, Jorge Costa and Vítor Baía, went on to dominate Portuguese football the following years.

[45] Mourinho gradually became a prominent figure of the club's staff by translating at press conferences, planning practice sessions and helping players through tactical advice and analyses of the opposition.

He quickly identified several key players as the backbone of what he believed would be a perfect Porto team: Vítor Baía, Ricardo Carvalho, Costinha, Deco, Dmitri Alenichev and Hélder Postiga.

Porto lost the 2004 Taça de Portugal Final to Benfica in May 2004, but two weeks later, Mourinho won a greater prize: the UEFA Champions League, with a 3–0 win over Monaco in Germany.

[76] Under Mourinho, Chelsea secured their first top-flight domestic title in 50 years, setting a string of English football records in the process, including the most points ever achieved in the Premier League (95) and the fewest goals conceded (15).

Their opening game in the UEFA Champions League saw them only manage a 1–1 home draw against the Norwegian team Rosenborg in front of only 24,973 (an almost half-empty stadium), which included an unimpressed owner Roman Abramovich.

Despite his domestic successes in winning the Scudetto by a 10-point margin, Mourinho's first season in Italy was viewed as disappointing by some Inter fans, as the club failed to improve on the performances of his predecessor Roberto Mancini in the Champions League.

Mourinho signed Argentine striker Diego Milito, who fell just one goal short of winning the top scorer award with Genoa, as well as Thiago Motta and Wesley Sneijder, to bolster the midfield.

Mourinho's team improved dramatically after that, as he built a formidable midfield with Sneijder at the heart of it and the likes of new signing Thiago Motta and veterans Javier Zanetti and Dejan Stanković.

Mourinho was sent off in the December Derby d'Italia away fixture after he sarcastically applauded the referee for what he felt was a dubious free-kick given to Juventus and Inter went on to lose 2–1, courtesy of a Claudio Marchisio winner in the second half.

On 5 May 2010, the team won the Coppa Italia, defeating Roma 1–0, and on 16 May 2010, Inter beat Siena 1–0 to secure the domestic double, accomplishing the feat of winning all trophies available for a manager in the Serie A.

[116] On 30 November 2010, Mourinho was fined £33,500 for appearing to instruct Xabi Alonso and Sergio Ramos to attempt to receive a tactical second yellow card in the 4–0 Champions League win against Ajax.

At the Bernabéu, Real's Pepe was dismissed in the 61st minute and Mourinho was sent to the stands for protesting; afterward, Barça's Lionel Messi scored two late goals to take control of the tie.

[140] Mourinho was also criticised[141] for controversial incidents, including poking Tito Vilanova (then assistant coach at Barcelona) in the eye during a brawl, continual complaints about refereeing bias, clashes with journalists and Real officials, and frequent hints that Barça received favourable treatment from UEFA.

[142] Three days later, Real Madrid president Florentino Pérez announced Mourinho would leave the club at the end of the season by "mutual agreement", a year after signing a contract extension to 2016.

This match marked the first competitive action for new signings Diego Costa, Cesc Fàbregas and Thibaut Courtois, the latter starting in goal after a three-year loan spell at Atlético Madrid.

[222][223][224] In order to reinforce the team for the second part of the season, in the winter transfer window, Roma signed Ainsley Maitland-Niles and Sérgio Oliveira, both on loan from Arsenal and Porto, respectively.

After enduring a difficult start to the season, with the club near the relegation zone, on 17 September, Mourinho registered the biggest win in Serie A since April 1961, when Roma thrashed Empoli 7–0 at home.

This forced United manager Alex Ferguson to move Danny Welbeck from the midfield to that flank, thus freeing Xabi Alonso, and two quick goals turned the game in Madrid's favour.

[322][323] On 20 December 2008, after Maicon scored the late winning goal in a difficult away match against Siena, which ended 2–1,[324] Mourinho wildly ran in front of the tiers reserved to Inter supporters to celebrate, hugging the Brazilian himself.

At the end of the first half, the Inter manager made a handcuffs gesture towards a camera which was considered by the Italian Football Federation as violent and critical of the refereeing performance, and caused a three-game ban against Mourinho.

[374] On 28 February 2023, Mourinho got yet another red card two minutes into the second half during a 2–1 loss to Cremonese, where he was supposedly spoken to and provoked by the fourth official in a disrespectful manner, which resulted in him having the reaction that had him penalised.

[378] In collaboration with DAZN, in 2019 Mourinho appeared in The Making Of series, a 3 part documentary which relives the significant games that helped define football's greatest modern icons.

[388] Widely known for his strong personality, refined dress sense,[389] and quirky comments at press conferences,[390] Mourinho has experienced fame outside of football circles, featuring in European advertisement campaigns for Samsung, American Express, Braun, Jaguar and Adidas, amongst others.