It was a moment of hugely uncomfortable difficulty, but also one that revealed an awful lot. Far more than Jose Mourinho's repeated insistence he would not be discussing Andre Villas-Boas any further.
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Toward the end of the broadcast section of Chelsea's news conference, after the Stamford Bridge manager stated there had been "enough" questions regarding his Tottenham counterpart, he was asked by a continental journalist about the late Bobby Robson's mentoring of both Portuguese coaches. The English manager first appointed Mourinho as his interpreter at Sporting Lisbon in 1992 before striking up a friendship with his young neighbour in Oporto by the name of Andre. Robson never employed Villas-Boas but did have significant input in his career.
The question was well-meaning and an understandable angle to the first fixture between the two Portuguese. Because English was not the journalist's first language, however, it was rather clumsily phrased. Yet Mourinho's response was anything but clumsy. It was curt and cutting, clearly designed to make a point. The words as written down don't fully reflect the sternness of the tone.
"We know how Bobby Robson has been important in your career and Villas-Boas' too," the questioner began.
"What?" Mourinho interjected.
"Bobby Robson has been important in your career ..."
"He was like a teacher ..."
"Why? I don't know," Mourinho said of Villas-Boas' relationship with Robson. "It's something new you're telling me."
Eventually, after a few moments of many in the room wanting to look away, the journalist asked whether "the spirit of Bobby Robson will be at White Hart Lane."
"Why?" Mourinho again asked. "Where he worked with Andre? I don't understand."
The journalist may have been caught in the crossfire, but the intended target was clear. In their seven years of working together -- from when the Chelsea boss appointed Villas-Boas as his assistant manager at Porto -- the two would have of course discussed their mutual connection with Robson. Therefore, this seemed to be a more painful put-down than any number of comments about behaving like a "kid" or how the "relationship broke down" as Villas-Boas put it. It was also in keeping with a news conference in which Mourinho clearly wanted to be seen as above any public dispute with his old employee but seemed to deliberately leave a number of indirect digs.
Some have argued the Chelsea manager is not especially impressed with how only one of the two makes such public play of their relationship with Robson. This, however, should not be perceived as a battle for the English great's legacy. It has become about so much more.
There are certainly a number of other fractious elements serving to deepen the emotion around Saturday's fixture at White Hart Lane -- not to mention over a century of history. Most recently, Chelsea's hijacking of Tottenham's deal for Willian exacerbated existing tension between the clubs' hierarchies, with Villas-Boas not unreasonably stating that it revealed Stamford Bridge's attention to the evolution in North London. It was one area where the two Portuguese coaches found common ground beyond their own history, as Mourinho described Spurs as "a big contender."
Going further back, there was the manner in which Villas-Boas initially seemed to follow his former boss' career and went from Porto to Chelsea, with many at Stamford Bridge well beyond the playing squad not exactly enamoured at how the younger Portuguese conducted himself. Villas-Boas, for his part, had justifiable complaints at his treatment by the West London side.
That has led to the current faceoff. It has all built up to one of the most basic dramatic narratives, a personal duel between two former friends who used to enjoy a master-apprentice dynamic. As to why that fundamental relationship between Mourinho and Villas-Boas broke down, there are few exact details or fully objective views -- just a number of theories and possible explanations.
The Tottenham manager intimated Thursday that it was down to his overt willingness to better himself.
"Our breakup point was because I was full of ambition to give him something extra [at Inter] and I wanted further involvement for the job I was doing at the time, which was scouting and match preparation," Villas-Boas said.
Mourinho might reasonably point to his warmer relationships with the likes of Brendan Rodgers and Steve Clarke and made a deliberate reference to his respectful exchanges with Louis van Gaal -- who was his boss at Barca -- ahead of the 2010 Champions League final. The Chelsea boss ended up winning that one. He is understood to still see himself as well ahead of Villas-Boas. This, it must be said, is something the Spurs boss recognises.
The news conferences of the past two days were not all discord and difficulty. Villas-Boas praised Mourinho's methods and how much he learned from them.
"I think there is always an influence because, when you've worked so close together for seven years, you learn methods that not only brought Jose so much success but you want to get to know those methods and apply them as well," Villas-Boas said. "There are probably lots of things in my organisation I do similarly to him, of course.
"I don't think there's anything to prove. Jose's career speaks for itself, and I'm very proud of what I've done so far and what I've achieved."
Mourinho's main problem this weekend is understood to be the idea that Villas-Boas would bring it all into the public domain so readily, as implied by stating he didn't want to "be a kid" and discuss it with the media. For all Villas-Boas eventually spoke on it, however, he did begin Thursday by stating that the managers should "be secondary figures to a spectacular game."
It is the very idea of spectacle that could actually be part of the problem. In the Lansdowne Road news conference room just after Porto's 2011 Europa League win -- and just two years after he had left Mourinho at Inter -- Villas-Boas made mention of it in an intriguing dedication: "Pep was always an inspiration to me when I left Inter because of his methodology and the way he plays such fantastic football. His philosophy is Barcelona's philosophy. He defends the spectacle of the game. Jose introduced me to professional football, so I'd also like to dedicate this to him and to someone who has already left us but was decisive in my career: Sir Bobby Robson."
Given that Mourinho's rivalry with Guardiola was at its most rancorous point after the 2010-11 Champions League final between Barcelona and Real Madrid, it would not be a stretch to interpret Villas-Boas' statement as somewhat loaded. The current Spurs boss seemed to be aligning himself with one side of the dominant tactical debate that has defined football for the past half-decade: Mourinho's reactive approach against the proactive appeal of the Catalans and Spain.
As superficial as all of this may seem, that could yet define and decide this fixture. Both managers have admitted seeking to alter the emphasis of their teams' play this season, something that has seen positives and negatives for both. Tottenham are waiting for so many attackers to jell, temporarily offsetting the process through a tighter approach -- one that has yielded only five goals in five games but seen their defence breached just once.
Chelsea have wrought a similar record with six scored and two conceded. That indicates a tight match, even if the two men in charge are now so much more distant. For all the drama of the buildup, it may need a proper on-pitch incident to ignite this game.
As for the handshakes? That could be another uncomfortable moment.