For 14 years, journalist and TV presenter James Richardson was the man who brought Italian football into UK homes as the front man for live Serie A coverage and the peerless Gazetta Football Italia show.

Last week he was reacquainted with Carlo Ancelotti when he came to interview the Chelsea manager at Cobham for a forthcoming edition of Four-Four-Two magazine. The official Chelsea website took the chance to turn the tables on the interviewer and ask James for recollections of the Ancelotti he observed building a big reputation in Italy.

To what degree were you aware of Carlo Ancelotti when you began covering Italian football for television in 1992?
'He had just retired from playing and was probably at that point assistant manager to Arrigo Sacchi with the Italian national team. I had been following the Italian game a while before that so I was aware of Carlo from playing in the Italia 90 World Cup. He was quite a distinctive figure as a player with his smooth cheeks.

'He is such an affable person that everybody gets on with him. He's a man in touch with life's simple pleasures. He had a fairly fast rise as a manager. He did great work in the second division and then he was at Parma which was the first time I actually met him.

'He went to Juventus where he didn't have the happiest of times but it was a very difficult situation. The Juve fans tend to be fairly snobby about all sorts of things, especially who is in charge of their football team, and there was a feeling that he wasn't the right man. His Parma team had been Juve's big rivals in almost every competition for a while, plus there was the fact that he had been a Milan player as well.

'But Carlo was a great person to speak to, a very intelligent man, very open, and he always seemed to find himself in interesting situations as well. So he was always someone we would try to interview and we would get to do that a couple of times a season.'

There is a story that the announcement he was to leave Juventus was made at half-time in the final game of the 2000/01 season when the team were not mathematically out of the title race.
'It must have been well known in the club before then because I remember interviewing [returning manager] Marcello Lippi before the end of that season, and it must have been a maximum of a couple of days after the end of the season that they had a press conference with Lippi and [assistant] Roberto Bettega because we were able to cover it for our broadcast. So it must have been all in place.'

He took over Milan following a period of instability for the club in terms of manager.
'He followed Fatih Terim, and he was about to take over at his old club Parma again, who were having an equally unhappy time. One of the few controversial things he did in his career was basically standing up Parma and going to Milan. Obviously Milan is a completely different job than Parma and thank heavens he did from Milan's point of view because he did a brilliant job there.

'It was a difficult time when he began. It was a club that under [Silvio] Berlusconi got used to being the best in the world. They had a series of problems and I think Carlo was a return to Berlusconi's desired way of doing things which was going within the Milan family. It is true Sacchi had been a major departure from that, and that had been Berlusconi's choice, but with Ancelotti, not only was he coming in but a whole load of players from that same Milan era were there - Galli, Baresi, Tassotti who came in with Ancelotti. They populated the various levels of player development there. It was consciously a back-to-the-future style move.

'The weird thing was that when he went to Milan, he had a reputation as being quite a traditional, tactically-rigid 4-4-2 manager. Famously he was the one who sold [Gianfranco] Zola to Chelsea when he was the Parma manager. Equally, Roberto Baggio was supposed to be signing for Parma and the deal was done but it is said Ancelotti said I don't want this guy in my team.

'He had a reputation for being this guy who didn't have any time for the Number 10, the fantasista, yet within a few months at Milan he was fielding four in one side. So there was a real tactical inversion compared with what had gone on before. Maybe he was given a freer hand at Milan which would be ironic because it always seemed like he wasn't given a free hand with Berlusconi leaning over his shoulder.'

Is eight years in charge of a club like Milan a rare and special achievement?
'It is a very long spell. I'm trying to think of who would be comparable and I am failing. Capello had a couple of stints but the longest of those was five years.

'The last three or four years of Ancelotti it was always being said that he will be gone by Christmas, he won't get to eat his panettone as the saying goes. But each time he turned it around. I don't think they were saying that because he wasn't a good manager, just because the situation was increasingly difficult. Milan were increasingly running on the fumes of what had been in the tank, if you know what I mean.'

The middle stage of Ancelotti's Milan career, the football played was portrayed in as more stylish and entertaining than the Serie A norm
'There is a massive stereotype about Italian football, which in many ways Milan typified under Fabio Capello, especially the famous season when they won the league scoring 36 goals in 34 matches.

'To be fair that was Capello reacting to adversity because Marco van Basten had gone in for a routine ankle operation and never came back. So they basically had four defenders in one of the great back lines, and they stuck Marcel Desailly in front of that, so there was no way anyone was scoring any goals.

'That typified a very defensive phase all the way through the 1990s which to be fair, Ancelotti was part of. His teams weren't particularly free-scoring but at Milan it was quite the opposite. There was a sudden return to the importance of the Number 10 in Italy and that was keyed by Milan where you had Rui Costa, Rivaldo, Seedorf and Pirlo all in the same line up. Then you had Kaká taking the place of Rivaldo. They played the most entertaining football. It didn't always work but when people gave them time and room to play, they were a great side.'

If people wish to find fault in Ancelotti's record at Milan they tend to point to just one domestic championship in eight seasons. Was he unfortunate not to win more?
'First you had Juve dominating and then the last couple of years Inter. Both of those last two seasons you have to have asterisks next to them because of Calciopoli [the match-rigging scandal involving influence on referees, mostly by Juventus]. There was also the fact that the Milan side, because of age and health, could do well in the cup competitions but wasn't really built for a league run.

'The season after Calciopoli in 2006, Milan were playing catch-up. He started with an eight-point deduction and they had their summer planning massively disrupted because until late on they didn't know whether they were playing in Europe, whether they were playing in the second division. They weren't able to make the signings they were expected to make, and they had to call players back from holiday to the training camp because they suddenly found themselves in the preliminary rounds of the Champions League.

'So the whole thing was a mess, and Inter in the mean time had reinforced massively so it should be seen within the context of what was a very complex situation.

'Even at Juve Ancelotti came second twice in a row which is not a disgrace and if I remember rightly he was let down very badly by Edwin van der Sar. My impression was they were a goalie short of being a really good side.

'But Milan were an advert for football when they were paying well and three Champions League Finals in five years, two of which were won is very impressive.I'm not sure how many managers have come close to that in the last 20 years.'

The interview continues tomorrow when James Richardson's views widen to include other Chelsea personalities who have worked in Italy, including Gianfranco Zola and Jose Mourinho.