#AskGregory Part One: John on Collymore, Yorkie and Lambert
And the 58-year-old was so expansive with his replies that we have decided to split the intriguing question and answer up into two-parts.
Find below his thoughts on Stan Collymore, Dwight Yorke, Olof Mellberg and Bruce Springsteen.
Q] Who is the most talented footballer you have managed at Villa?
A] Stan Collymore! He was the most talented footballer that I have ever worked with! He had more talent than anyone I have ever worked with in my life.
On the Thursday afternoon before my first game against Liverpool in February 1998, we had a training session at Bodymoor Heath and we were concentrating on finishing. Someone crossed the ball and Stan headed it home. One of the coaches came up to me and said: "You've cracked it with Collymore, you know!" I said: "What do you mean?" And he said: "That's the first time he's headed the ball in six months."
When I came back, Stan was the only player that was different from when I had left 18 months before. He was the only addition. I knew everyone else. I had worked with everyone else. Simon Grayson, Fernando Nelson, Ian Taylor, Savo Milosevic and Lee Hendrie, all of them. They were all there when I was there.
I was thinking: "What's all this fuss about Stan. He's a great player!"
And then, against Liverpool, he chased full-backs, won headers, he used his right foot, left foot, showed his power. He was just sensational on that particular Saturday. He scored two goals in the 2-1 win. I took him off in the 77th minute to a standing ovation from Villa Park. I just thought, genuinely, "What's all the fuss about?"
Then the following Tuesday, we went to Athletico Madrid for the first leg of the UEFA Cup and I had to take him off five minutes after half-time!
He was quicker than Thierry Henry. He was better in the air than Thierry Henry. He had better feet than Thierry Henry. He was strong and powerful. When he stripped off, he had six per cent body-fat. His skin was like an elastic band. He was so fit and healthy.
My god, what a player! He was the most talented. It was my biggest regret that he didn't produce it regularly enough.
Q] Who's your favourite all-time Villa player?
A] I have a few! I'm going to miss one or two and I apologise in advance for that.
Paul Merson was the magician. He was an incredible match-player. He won us games on his own sometimes just with his sheer brilliance. He could create stuff that other people couldn't even dream of. He could see passes others couldn't - and he could execute too.
He scored some brilliant goals too. I really think in the later stages of his career, Villa got some real quality time out of him.
The lads loved him too because Merse was a trier. He worked his socks off every week. He gave you everything he had.
Some weeks it just wasn't there for one reason or another but most weeks it was.
I had a lot of empathy for him because he was going through a lot off the field. We had regular meetings in the week in my office and if he wanted a day-off I'd give him a day-off. I could get inside his head and I knew what made him tick.
He loved playing football and I think we got two seasons out of him later in his career.
I loved working with Olly Mellberg. He was brilliant. Gareth Southgate was a brilliant captain. He gave everything every week. On the training ground he was a proper captain. He led by example all the time. You don't get 50 plus caps for England if you're not a good player.
I have to add Lee Hendrie. I loved him. He was a naughty schoolboy most of the time but he had a lot of talent. He loved the Villa and he gave blood every single week.
He ran himself into the ground. He was a little slip of a thing. He weighed about nine stone wet through - he had to run around in the shower. But he always had a smile and he was a fantastic trainer.
He had an abundance of energy and he was there, doing it, every Saturday. He gave it everything he had.
I am sad to hear what's happened to him over the last few years. I think we got the best out of him.
Q] How do you think Villa will do under Paul Lambert this season and in the coming years?
A] When Paul came into the Barclays Premier League with Norwich, he'd been with the club for two years previous. He had shaped Norwich. He had put his own stamp on Norwich.
When he arrived into the top-flight, every player knew what their job was on the field. They had been doing it incessantly for two years.They'd had Paul in their earholes telling them what he wants and he expects. They knew what was required.
These guys, they are just learning. Paul has been only been at Villa for about ten weeks. It takes time to change people - their habits. It will take a little time to bed in.
I think he has brought in young players because he can still change their habits. It's tough when you bring in old pros, at 29, 30, to make them think differently or act differently. But he's brought in young and hungry players who will learn what Paul wants of them.
There will be a few hiccups between now and Christmas but I think this group of players given time and coaching will eventually hold its own in the middle of the table this season.
We can't expect Champions League or Europa League yet. If we get in that top half, it will have been a good season.
But Paul is still learning. He's finding out about Stephen Ireland. He's discovering what makes Darren Bent tick. He doesn't know - he's never worked with him before. He learns more about them every day.
He will find the right balance, which combinations go well together. Things will be good for Villa, I'm sure, but it will just take a little time. You can't make an omelette without breaking an egg!
Q] What's your favourite Bruce Springsteen song?
A] Oh jeez. If I really had to nail it down, it would have to be Thunder Road from the Hammersmith Odeon in 1975.
You have to realise that was Bruce's visit to England and his first concert in Europe. He came over with his big reputation and there were posters put up all around the theatre, which is still there and called the Hammersmith Apollo, saying 'Is London ready for Bruce Springsteen?'
Bruce went absolutely berserk and ripped them all down from the walls. He nailed it on the first night and that was his first song that night.
That song has always stayed with me. Whenever I've been annoyed or angry after a defeat I've got in the car, put that on and it's helped me chill out.
Q] Did you ever sit down and sing Bruce Springsteen songs for the lads in the dressing room?
A] No! It never got that bad.
We played Charlton on the last day of the season and I can remember I asked the guys to put on the video of Born to Run for the lap of honour after the game.
We ended up losing 4-3. I was so, so angry that I ended up running around the outside of the pitch, clapping and waving at everyone, and then running down the tunnel because I couldn't wait to get out of the way.
That's the only time I have every shoved Bruce Springsteen down anyone's throat.
I do remember playing a gig once at the NEC for the BRMB Music Awards with the Swains. I saw quite a few of my players - Ugo, Gareth etc - in the audience and I remember thinking: "I've had to sit through some of your performances. Now you'll have to sit through one of mine."
Q] Do you still use your Villa number plate?
A] I actually sold it!
I was abroad and hadn't driven that car for two years. It was in the garage with a cover over it. When I came home, I didn't get it out. I only came home for three or four days at a time.
I ended up not insuring the car because it was £500 - and I wasn't even using it. I took it off the road.
When I finally did get round to using it again, I had to put a new battery in it.
We decided to sell the number plate because it just wasn't getting used enough. I sold it on to a Villa fan in Worcestershire. I just thought: "He's going to get real fun out of it."
Q] Who was your best pound-for-pound Villa signing?
A] That was Olly Mellberg. If you compare the valuation on him and what we got back in return, it was probably the best piece of business.
Saying that, the deal for Dion Dublin comes very close.
At the time he had a clause in his contract saying that if someone bid £5m for him, Coventry had to accept it. We did bid and that triggered the clause. They couldn't turn it down.
He scored two in his first game. He scored another against Tottenham that day but it got ruled out. We later found out on Match of the Day that he was actually onside. He gave us a lot - an extra dimension up front.
Merse wasn't expensive either. We got great value out of him. George Boateng was relatively cheap. There was Mark Delaney too, who cost £500,000. He gave great service.
I have to say, and not many people talk about him, but David James did brilliantly for us.
We paid £1.5m for him from Liverpool Reserves and he was outstanding. He got back into the England squad on the back of his performances for Villa. He did great.
When David made a mistake, everyone started up with: "Here we go again, Calamity James."
I can remember his first mistake for Villa was after 31 matches. He dropped a cross or did something silly and everyone just jumped on the 'Calamity James' bandwagon. It was totally unfair!
We ended up selling him to West Ham for £3.5m! It was a good profit. Doug was happy! Then we ended up signing Peter Schmeichel on the back of it.
Q] When you were top of the table at Christmas 1998, did you truly believe you could win the title?
A] No!I didn't truly believe we could win the title. But I really thought we could hang in there for the remainder of the season and be a threat.
As it turned out, we were not a threat, we slipped away and finished sixth.
Ugo Ehiogu got a kick in the eye from Alan Shearer and he was a big miss.
I thought we would be able to stay in the top three or four. I could still see us with three or four games to go having a chance of winning the league.
In my heart, it was a yes but in my head, I knew we wouldn't have the longevity - the squad wasn't deep enough. If we had one or two injuries we wouldn't be able to cope. That's how it proved.
Q] Is Dwight Yorke still a fugitive?
A] I knew he wanted to go to Manchester United. That wasn't what the argument was about. Ultimately they paid the fee we wanted.
We played against Everton on Saturday. We drew 0-0. And Yorkie never broke sweat. He sulked for ninety minutes. He just let us know that he didn't want to be there. We just dug our heels in even more.
He came into my office and uttered those immortal words: "I don't want to play for Villa anymore." That hurt me!
The Manchester United thing didn't bother me. But when he said: "I don't want to play for Villa anymore" I felt terribly insulted.
Fortunately I had left my gun in the car that morning. But, saying that, I wasn't about to murder one of Villa's most famous strikers.
But I thought: "You can't say that." I felt it was an insult to me and the club.
But we've seen each other loads of times since and it's always a big handshake and big hug. We're absolutely fine.
Watch out for Part Two tomorrow as Gregory discusses Deadly Doug, his FA Cup final regrets, his fine mop of hair and his reasons for leaving.
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