Between them, Real Madrid manager Carlo Ancelotti and Manchester City boss Pep Guardiola have lifted the European Cup as player or coach a remarkable nine times. When this greatest competition in the history of club football reaches its 70th birthday in three seasons’ time, the profiles of the Italian and the Catalan — each born in tiny communities whose combined population wouldn’t fill a third of the Santiago Bernabeu — will be written into Champions League history books as the greatest the competition has ever seen.
Ancelotti, even though he might one day be overtaken by Zinedine Zidane or Guardiola himself, has won more European Cup finals (four) than any other coach. Ever. Guardiola will be on that pantheon in three years’ time because it’s his Barcelona side of 2011 that is widely hailed as having produced the most magnificently complete performance in any Champions League final — although some who witnessed Madrid’s 7-3 defeat of Eintracht Frankfurt in 1960 might argue otherwise.
Despite all this, the men who meet in Tuesday’s semifinal first leg (and then again in the return leg in eight days’ time) also have a deeply quixotic, angst-ridden and painful relationship with the competition. For them, this trophy is the definition of a love-hate relationship; can’t live with it, can’t live without it.
For example: Guardiola was in charge of Bayern Munich when, in the 2014 semifinals, they suffered their heaviest-ever home defeat in the history of the competition. Coincidentally, it was to Carlo Ancelotti’s Madrid.
As a player, he’d have been able to add another title to the nine he and the Italian have, were it not for the agony of the equal-biggest thrashing any team have taken in a European Cup final. Johan Cruyff’s Barcelona were in their second European Cup final in two years, and a supposedly under-strength Milan — missing a clutch of stars — smashed the Catalans 4-0 in Athens, heralding the end of the Dream Team era and presaging Cruyff’s departure two years later.
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Guardiola has coached six losing semifinal teams in his 15-year managerial career. It is an absolutely stellar record in terms of “you can’t win it unless you’re in the mix in the decisive stages,” but ultra painful in the “close but no cigar” stakes.
Equally, his teams’ eliminations in the final four have often been remarkable, bordering on the bizarre.
There was that 4-0 home defeat to Real Madrid nine years ago, which he still calls the greatest tactical mistake of his career. Beaten by the eventual winners.
Then there was the volcanic eruption in 2010 that meant his Barcelona team had to undertake the journey from Catalunya to Milan by bus because flights were grounded. Inter Milan eked out a 3-2 aggregate victory, with 10 men in the second leg. Beaten by the eventual winners.
Barcelona missed a penalty (well, Lionel Messi missed a penalty, to be more precise) to go 3-2 up on aggregate against 10-man Chelsea in the 2012 semifinals. Beaten by the eventual winners.
Then, the mother of all results: last season, Man City were leading 5-4 in Madrid with 91 minutes of the semifinal second leg played, and they still got knocked out. You know the payoff: beaten by the eventual winners. Again.
People make a lot out of this. Some choose to highlight these stumbles at the penultimate hurdle rather than, first, acknowledging that Guardiola is already, demonstrably, one of the all-time great coaches. He has been a revolutionary, game-changing, inspirational, successful coach across three very distinct footballing cultures.
He’s had a very different problem to either Ancelotti or, indeed, any Real Madrid coach.
Guardiola, throughout his time at City, has actively had to try to convince the English players, in particular, that the Champions League matters as much, if not more, than winning the Premier League. Kevin De Bruyne stated recently that being champion of England mattered more to him. Even Guardiola himself said a year ago that if he had to “sign right now” for one of the two trophies, it’d be the Premier League.
That’s not the case at Madrid, nor has it been emblematic of Ancelotti’s career.
His two principal homes, Milan and Madrid, are the two clubs that have won the European Cup most often: 14 times and seven, respectively. At each club they view the trophy as part of their birthright, Madrid particularly so. Dominating the noisy neighbours — winning Serie A or LaLiga, at the expense of Inter and Atletico Madrid — still matters very much, but sitting on the European throne and lording it over a continent is something Ancelotti has thrived upon at both clubs.
Six times he’s worn that crown: as a midfielder for the Rossoneri in 1989 and 1990, as their coach in 2003 and 2007, and then in charge of Los Blancos in 2014 and 2022. It’s a victory arc that’s stretched across 33 years. Pretty impressive.
Despite that, he too has been damaged, frustrated and taunted by this competition and the iconic trophy that everyone yearns to own — even if only temporarily.
Ancelotti’s first experience of how quixotic football’s holy grail can be was sitting in Rome’s Stadio Olimpico, injured, having helped steer AS Roma to the 1984 final, only to see Liverpool win on penalties.
In 1991 he stood to win a consecutive hat trick of European Cup finals if Milan could beat Marseille in the semifinal. Losing 2-1 on aggregate in the closing minutes of the second leg, the State Velodrome floodlights cut out. Fifteen minutes later they flared back into life but Milan’s CEO, Adriano Galliani, refused to let his team play the remainder of the match and appealed to UEFA to hand the tie to the Rossoneri. He, his fans and Ancelotti were distraught to find that it was they, instead, who were kicked out of the competition by the governing body.
Ancelotti’s most famous night of dread came in Istanbul, at the same Ataturk Stadium where this season’s final will take place, when the 2005 final was lost to Liverpool (them again!) despite his team leading 3-0 at half-time. Righting that wrong became an obsession for the Italian, such that he admits to supporting two teams (Liverpool and Milan) in 2007, in the fervent hope they’d meet in the final again that season. They did. He won.
However, this competition is so elusive, dangerous and demanding that it’s not only in the ultimate knockout stages that it can wound you.
Ancelotti wrote in his book “Quiet Leadership” that in December 2012, with his Paris Saint-Germain side second in the title chase (they’d ultimately coast to Ligue 1 victory) and with their Champions League group already won, “… the president [Nasser Al-Khelaifi] and [director of football and former Milan player under Ancelotti] Leonardo came to tell me: ‘if you don’t beat Porto in the next game, you will be sacked. They came again, the day before the match, and both told me: ‘Win tomorrow or the sack.’ We won, played well, beating Porto 2-1, so I wasn’t sacked … but they’d made my position untenable so I told Leonardo, who I’d thought was a friend, that at the end of the season I would go. It should never happen like that in football.”
They are different faces of the same coin, Ancelotti and Guardiola.
The Italian is king of all he surveys: Spanish, European and world champion right now. He is the absolute master of man-management, the player whisperer, and someone who happily admits that his choice of playing style and tactics should be “like a tailor-made suit — made to measure for the players at your disposal.”
The Catalan is crown prince, on the verge of landing the fabled treble (winning the league, the domestic cup and the European Cup), and in the process would become the only coach ever to achieve it twice with two different clubs. He is a tactical genius but not necessarily addicted to arm-around-the-shoulder player whispering, someone for whom the playing style and tactics are paramount, for whom it’s the players who must adapt and change.
Neither of them will talk about obsession this week. Neither of them will hark back to the brutal, sleepless, agonising nights the quest for this trophy has dealt them. But now you understand their dark fears and their daring dreams. And here they go again.