When Liverpool return to Villa Park today, after nine months in which Gregory has made remarkably few other miscalculations, they will face a side which has won 17 and lost just two of their 23 Premiership fixtures in his charge. Unbeaten this season, Villa stand three points clear at the top, having made the best start in the club's 124 years and supplied three men to England's winning line-up on Wednesday.
Meeting the 44-year-old Gregory this week, in an office high in the North Stand where Bruce Springsteen videos are more likely to be playing on the television set than an agent's tape of an Italian striker, it was hard to believe that the man who is the Boss at Villa Park was with Second Division Wycombe Wanderers until late February.
"If ever something came along, totally unexpected, and punched me on the nose, it was being offered this job," Gregory recalled in typically forthright terms. With 20-20 hindsight, though, he seems almost to have been the logical replacement for Brian Little.
A versatile midfielder who would win six England caps, he occasionally captained Villa under Ron Saunders. But two years before the championship triumph of 1981, Gregory and the gaffer fell out - over pounds 25.
"They were paying me pounds 225 and I wanted the top line, which was pounds 250. Ron told me he had the chance to sell me to Brighton. I almost rushed away from here. All my life I'd lived on the breadline and suddenly there was a chance of making more money.
"If I'd had someone to advise me, I might have done things differently. I'm not saying for one minute I'd have been in Villa's European Cup-winning team, just that I passed up the opportunity to be part of it."
He also had a spell at Villa as Little's coach before leaving two years ago to learn how to manage. "When I was number one at Portsmouth (in the 1989-90 season) I was completely naive. I knew how to coach but had no idea about how to handle substitutions or deal with an angry player banging on my door.
"I needed to become my own man. I had visions of getting Wycombe into the play-offs or maybe even into the First Division, but never this."
The portents for Gregory's third coming were not promising. "We were in 15th place, Brian had gone and we couldn't win a match for love or money. The dressing-room was in uproar, fighting and scratching each other's eyes out. And I wasn't a popular choice with the fans. They wanted a big name."
In his favour was the rapport he had developed with the team as coach. However, there were only two days training before Michael Owen and co arrived. "My head was spinning and I had hardly slept, but I didn't have time to be nervous. If I'd come in June and we were playing Liverpool in August, I'd have crapped myself."
He may have felt like doing precisely that when Owen scored after just six minutes. Fortunately for Villa's laundry staff, Stan Collymore soon equalised and eventually secured the first of nine wins in the final 11 fixtures. Despite "the close season from hell", Gregory was confident they could pick up where they left off.
"We didn't let the external things affect our preparations," he said, referring to Collymore's fracas with Ulrika Jonsson, Dwight Yorke's determination to join Manchester United and David Unsworth's poor grasp of geography. "We'd get in at 10 in the morning, leave all the rubbish in the media to one side and work at what we're good at."
At first, what they were good at was watertight defence. Without obviously weakening their solidity at the back, where Gareth Southgate has made himself an early contender for the Footballer of the Year award, Gregory has grafted on Paul Merson and Dion Dublin for pounds 12.5m.
Reflecting his own natural ebullience, Villa are effectively playing three attackers, with Merson floating behind Collymore and Dublin. Lee Hendrie, languishing in the Pontins League before Gregory took over but now with an exciting cameo for England behind him, also has licence to roam. Suddenly the goals are flowing.
Yet the real test will come in their next five games, four of which are against "the big hitters" as Gregory calls them: Manchester United, Arsenal, Liverpool and Chelsea. "People say we've played nobody, but they haven't played us either. They also say they're not sure we can last the pace, the implication being that United wouldn't blow up in our position. But on 10th January they were 12 points clear of Arsenal. They still finished second.
"I'm not one for stats" - and you knew he was about to unleash a flurry of numbers - "but if we continue at our present rate of 2.33 points per game we'll finish with 89. Arsenal won it with 78 at 2.05 a game. We're also averaging two points a game away, whereas they did 1.6. We're well on course. We can definitely win the Premiership."
The figure, however, that has caught many imaginations is the 11 Englishmen he often fields. Watching Villa beat Birmingham in a reserve derby this week, Gregory was surprised and delighted when a supporter of their city rivals shook his hand and said he hoped the all-English XI won the title.
Home-grown by design or by accident? "A bit of both. The three foreign boys (Sasa Curcic, Savo Milosevic and Fernando Nelson) left because I felt they couldn't give a monkey's whether we won or lost. Nelson's a lovely lad but he had no real desire to fight for the cause.
"I've looked at the market in Europe and there's not too many I'd want to bring in. I wouldn't know what they're like as people whereas with Dion I knew his background and his family in Leicester. The same with Alan Thompson and Steve Watson. I could ring half a dozen contacts about them.
"The beauty with buying British is that you know what you're getting, which you don't in Europe unless you're someone like Ruud Gullit or Arsene Wenger and know the scene really well."
Besides, he added, he can ask Dion Dublin to make him a pot of tea but could not imagine Ariel Ortega fixing a brew. Nor, perhaps, would an overseas star have appreciated the manic game of indoor cricket (wastebins for wickets, one-handed catches off the wall) which Villa's squad were playing within 12 hours of their Uefa Cup exit against Celta Vigo of Spain.
The innings after the night before was "a bit of fun", Gregory explained, to revive spirits. "We tried to take something positive from the defeat, which was that we'd have more midweeks free to rest and prepare. Then we signed Dion and by the Friday we were having to hold the boys back."
Dublin, like his new manager, was attracted by the prospect of updating Villa's honours list. "There's an aura about this place," Gregory said, "a sense of history and tradition. Even the name is beautifully symmetrical, with five letters in each word.
"I was asked in the summer how I was going to attract players here. I just said: `This is Aston Villa'. To sell this club to players you only have to show them round. We're already big, even if it's a disgrace that we haven't won more. I want to make us massive, which means winning trophies on a regular basis."
Positivity personified. If it counts for anything, the Boss and his band will still be top of the bill when the curtain comes down in May.Reuse content