The first thing to report is that John Gregory is in good health. Sitting in a restaurant in central London, Gregory looks and sounds remarkably well for a man who underwent open heart surgery at the start of the year and it says much about the speed of his recovery that he is already talking about the next chapter of a managerial career that in recent times has taken him from Israel to Crawley via Kazakhstan.

That breathless feeling Gregory experienced after climbing a flight of stairs has gone and at the age of 61 his appetite for football management burns as strong as ever. “I’m in better condition than the vast majority of the managers in the game at the moment because my heart is perfect now,” says Gregory, who was referred to a cardiologist in December while in charge of Crawley. “It’s not a stress issue. I had a faulty valve, I’ve got a brand new one now.”

Gregory is in good spirits, enjoying life and free from any discomfort – at least that is the case until we discuss Saturday’s FA Cup final between Arsenal and Aston Villa and, in the same breath, row back to the last time when the Midlands club were in this position. The year was 2000, Chelsea were the opponents, Villa lost 1-0 and Gregory was in charge. A largely forgettable match was settled by a second-half Roberto Di Matteo goal following a mistake from David James. Except Gregory has never thought of the game in that way.

“Jamo got us there, he saved two penalties in the semi-final in the shootout. I’d never point a finger, I look at myself. I could have done more and I should have done more. I should have been more offensive, maybe put on another striker, risk losing the game 2-0 or 3-0 but have a go.

“You just put the trust in the players and maybe on the day there wasn’t too many in the team who performed as well as they had done in the league games that year. But it’s gone. And I’ve felt guilty ever since. It keeps me awake at night. Even now.

“We hadn’t been back there in the FA Cup since ’57, so it was 43 years. But we didn’t win it and that still haunts me. And to this day, I never ever want to talk about that final to people because we lost. It’s failure. And that feeling – and I talk about this with my family at times, you kind of look back and think: ‘You’ve done this, this, this and this, you ain’t done badly in your life.’ And it’s like: ‘Yeah, I know, but I didn’t win the FA Cup.’”

Gregory had appeared in the FA Cup final as a player for Queens Park Rangers against Tottenham Hotspur in 1982 and he tells a nice story about how he received a telegram beforehand from a former classmate that said: “Every schoolboy’s dream.” QPR were beaten by Spurs in a replay, courtesy of a Glenn Hoddle penalty, yet Gregory never felt anything like as bad about that defeat. With a manager, he says, the sense of responsibility is so much greater and even more so when there is an emotional attachment, which was the case with Gregory and Villa. He had played and coached at Villa before being appointed manager in 1998 and the overwhelming feeling at the end of that Cup final against Chelsea was that he had let people down.

“I had 40,000 Villa fans there that day and as I walked out the tunnel, in what was the old Wembley, all the Villa fans were at that end of the stadium. The sight was beautiful. It wasn’t just ‘wow’, it was a thing of beauty: ‘This is my team.’ I can see it all now still, it was just washed in claret and blue. The thought that went through my head, of course, was: ‘You’ve got to come back past this lot and back into the dressing room. Make sure you win.’”

At the time of the final Gregory had been Villa manager for a little more than two years and the one consolation for him in the wake of that defeat was that there was a chance to put things right in seasons to come. Yet despite taking Villa to the Premier League summit in three of his four seasons in charge, there was no silverware and Gregory resigned in January 2002 after becoming exasperated with Doug Ellis, the chairman at the time, for refusing to sanction the signing of Muzzy Izzet several months earlier. “We were top of the league and I couldn’t believe he didn’t want to make that jump to get another player,” he says.

Ellis, in Gregory’s words, “wasn’t the worst” and the two of them always exchange pleasantries whenever their paths cross these days, yet there were plenty of times when the Villa chairman would drive him round the bend, whether it was complaining about paying a right-back more than £10,000 a week or being stuck in a time warp. “I always remember I criticised our training ground once, before they rebuilt Bodymoor Heath, and Doug told me: ‘Bill Shankly said that’s the best training ground he had ever seen’ – which Bill Shankly had said. But he said it 25 years before. That was where it was hard sometimes dragging Doug into the next century.”

There were no shortage of egos in the Villa dressing room back then and Gregory shakes his head as he recalls some of the things he had to deal with while in charge. He remembers being in Cannes on holiday in 1998 and being criticised for not controlling his players in the wake of Stan Collymore physically assaulting Ulrika Jonsson. “I had the Women’s Liberation on the phone asking why I wouldn’t give them an interview,” he says.

Gregory’s Villa teams were, by his own admission, workmanlike rather than entertaining and so it was no real surprise that David Ginola’s move to the club never worked out. Although Ellis pushed and pushed to sign Ginola – “He came back from Mauritius, where he’d met David one summer and he was in love with him” – Gregory says that the deal would not have gone ahead without him agreeing to it. It was a decision that all parties would later come to regret, perhaps with the exception of Ellis, who seemed to enjoy having his photo taken with Ginola at various points.

The biggest problem for Gregory, who had been talked about as a potential England manager at one stage, was coming to terms with life after Villa. “I thought I’d never leave. I thought I’m going to be here for ever,” he says. “But I also remember saying to people very close to me when I left Villa: ‘It’s all down hill now.’ I knew it wouldn’t get any better than that. And that’s how it’s been.”

Gregory had spells with Derby and QPR before going out to Israel but he has always kept a close eye on things at Villa. Gregory is, essentially, a Villa fan, as anyone who follows him on Twitter would know. On the day of the semi‑final against Liverpool, Gregory posted a picture of himself next to the Villa dugout at Wembley, titled “The winners’ enclosure”. “That was before the game kicked off,” he says, smiling.

Gregory is full of praise for the job that Tim Sherwood has done since replacing Paul Lambert. “I think Tim’s been brave, he could have come in and taken a really cautious approach but he hasn’t done that. He’s selected offensive teams and I think that’s really commendable. You get a honeymoon period and Tim has now given himself until next January because he’s got all the fans onside. I follow a lot of Villa fans on Twitter and there is one guy who has basically made a full blown apology after slagging Tim off when he first came in.”

It is difficult to know where Gregory will show up next on the back of his last few experiences. He managed two clubs in Israel, Maccabi Ahi Nazareth and Ashdod, between 2009 and 2011, and thoroughly enjoyed his time in the country, even if he ended up pleading for a bit of rain on a morning to provide some respite from the sunshine.

Gregory has been back to Israel since and says that he never had any security concerns while he was out there. “When I was in Ashdod there was a little bit of trouble because Ashdod is right in the south, 25kms further than Tel Aviv, so you’re heading towards Gaza. So the sirens used to go off, every apartment has got a bomb room, which is lined with steel and the advice was always to go and get in that. But I never feared for my own safety. I’m realistic, get on with it, don’t spend your life worrying.”

As for Kazakhstan, the city of Almaty did not quite tally with the image that Gregory had in his head when he flew in to become manager of FC Kairat in 2011 and pictured Sacha Baron Cohen. “I landed, got picked up at the airport, there were Porsches, Mercedes, BMWs everywhere. And then we drove past a Bentley garage. I was thinking, obviously, Borat, pony and trap, and here were all these fantastic cars. It was like Mayfair.”

Gregory returned to management in England for the first time in six years when he took over at Crawley in 2013 and it is a source of frustration that surgery prevented him from seeing the job through – Dean Saunders was appointed on an interim basis in December – and having a shot at keeping the club in League One.

It is unlikely, however, to be the last time that we see Gregory in a dugout. “I think out there somewhere there will be a job for me,” he says. “If you’ve got the right financial backing, and the right support, and someone who has got common sense and doesn’t sit there reading the message board all day … I worked for Briatore at QPR, I had no chance, nor did the other nine that followed me in two years because it was all about Flavio and every decision appeared that he was just making it on a whim, similar with the guy at Leeds. But I’ll be ready to go back whenever it may be.”