José Mourinho was never destined for a quiet exit from the spotlight. This truth will likely feel like an ongoing torment for Real Madrid as they get ready to confront Benfica, with their UEFA Champions League aspirations hanging in the balance.
Having witnessed the “Special One” transform into the “Normal One” over three contentious years at the Bernabéu between 2010 and 2013, Madrid is familiar enough with Mourinho to anticipate a final twist when they face his Benfica squad for a spot in the round of 16 over the coming eight days.
Mourinho has already revisited his former club to vex them this season by orchestrating Benfica’s astonishing 4-2 league-phase triumph last month – secured by goalkeeper Anatoliy Trubin’s remarkable header in stoppage time – which pushed Madrid into the playoffs and kept the Lisbon team in contention. The two sides were subsequently drawn against each other to meet again this Tuesday at Estadio da Luz, prior to next Wednesday’s return leg in Madrid.
However, with Mourinho rumored to take over from Roberto Martínez as Portugal’s coach after the 2026 FIFA World Cup, each Champions League fixture could potentially be the 63-year-old’s final one. This particular encounter couldn’t be a more appropriate occasion for Mourinho to postpone his Champions League farewell – a match in the competition that established his reputation, played against the club that undermined it.
Would Mourinho be the kind of individual to derive immense satisfaction from exacting retribution against Madrid, 13 years post-Bernabéu departure, by eliminating them from the Champions League? Without a doubt.
It is accurate that, since his three-year tenure as Madrid coach concluded in 2013, having secured only one LaLiga title, one Copa del Rey, and one Supercopa, Mourinho has garnered more significant accolades than most other managers. Yet, he has consistently been one to benchmark himself against the elite, rather than the rest.
He claimed a Premier League championship with Chelsea in 2015, the UEFA Europa League with Manchester United two years later – additionally winning League Cups during his stints at Stamford Bridge and Old Trafford – and the UEFA Conference League with AS Roma in 2022. Nevertheless, the truly monumental achievements on Mourinho’s resume occurred before he arrived at the Bernabéu and engaged in the dual challenge of managing a skeptical locker room while simultaneously contending with Pep Guardiola’s Lionel Messi-driven Barcelona side.
Prior to assuming leadership at Madrid, Mourinho was a consistent victor – Champions League triumphs with FC Porto and Inter Milan (the latter as part of a Treble), numerous domestic cups in Portugal, England, and Italy, and six league titles in eight years with Porto, Chelsea, and Inter.
He accumulated 17 trophies during those eight years, but only nine in the 16 years since, with Madrid, Chelsea (again), United, Tottenham Hotspur, Roma, and Fenerbahce. The decline began at Madrid.
At the Bernabéu, conflicts arose with powerful and influential senior players, including Iker Casillas and Sergio Ramos, and he also lost his aura of invincibility during a fierce rivalry with Guardiola. Having previously commanded unwavering loyalty from prominent players at Porto, Chelsea, and Inter, Mourinho lost that bond at Madrid, and it never resurfaced, leading to comparable disputes with star players – Eden Hazard (Chelsea), Paul Pogba (Man United), Dele Alli (Spurs) – during subsequent managerial positions at other clubs.
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Was José Mourinho Fortunate in Benfica’s Playoff Advancement?
Gab Marcotti and Julien Laurens analyze the dramatic conclusion to Benfica’s encounter with Real Madrid, where goalkeeper Anatoly Trubin shocked everyone by netting a last-minute header to propel Benfica into the Champions League playoffs.
Sources who collaborated with Mourinho during his two stints at Chelsea assert that he underwent a character change in his second tenure. His period at Real Madrid left lasting imprints, rendering him a more confrontational, less favored figure within both the team’s locker room and the executive board. Mourinho has also been unable to restore his reputation for winning major trophies, despite coaching at some premier clubs, and consequently, his coaching opportunities have diminished in appeal with each rotation of the managerial carousel.
Publicly, Mourinho has declared his time at Madrid a highlight. He stated to Portugal’s Channel 11 in 2019: “Real Madrid represented my peak experience due to what I assimilated as a coach and as an individual, from the lessons I gained in my career and in my personal existence. It stands as the finest memory of my professional journey; it was magnificent.” However, circumstantial evidence suggests a different scenario.
While it was the most significant role of Mourinho’s career, it concluded with a sense of unfulfillment and a failure to meet the success benchmarks anticipated by both him and Real; his time at the Bernabéu will forever be associated with a feeling of “what could have been.”
Regardless of his previous workplaces, Mourinho has consistently retained the knack for generating headlines, and the 4-2 triumph against Madrid last month exemplified classic Mourinho. Had he not instructed his goalkeeper Trubin to advance in a desperate final gamble, Benfica would have failed to score the pivotal goal necessary to enter the playoff round, thereby precluding this week’s two-match series with Madrid.
Mourinho has not managed a team at the Bernabéu since his departure in 2013 – though he led Inter to Champions League glory against Bayern Munich at that very stadium in the 2010 final – so his return to Madrid for the second leg next week is set to stir a myriad of feelings, both for Mourinho and the home fanbase.
Therefore, Real Madrid has ample reason to approach their re-encounter with Mourinho with caution. He just might seize one final moment in the Champions League limelight.
