Far from thinking negatively, Gregory enhanced the upbeat mood of the Villa party yesterday by confirming the appointment of Steve Harrison as first-team coach. Harrison, a self-confessed prankster and impressionist, thus returns to the club he served in the same role for seven months during Graham Taylor's reign.
Since leaving to take charge of Watford in January, 1988, Harrison has, in his own words, "done more miles than Michael Palin". After an unsatisfying sojourn at Vicarage Road, he went on to coach at Millwall and, fatefully, alongside Taylor with England.
Revelations about his lavatorial party piece cost Harrison both jobs in 1991, yet he re-emerged with Crystal Palace and was later reunited with Taylor at Wolves. More recently, he has been coaching Preston. After last week's reserve fixture between Villa and the Lancashire club, Gregory offered him the opportunity to come full circle.
Having expected to be involved in a Second Division match against Luton tonight, Harrison found himself preparing Villa to face the side who trail only Real Madrid and Barcelona in the Spanish League.
For all the seriousness of the task, he guaranteed that he would approach it in good heart. "I've always thought players worked better with a smile on their face. If you know how to make them laugh, you've got a chance of getting the best out of them."
Harrison has, however, assured Gregory that he has put his old trick behind him, as it were. "It was a long time ago and I've served my time," he said.
Gregory admitted that the rapport Harrison enjoyed at Palace with Gareth Southgate and Stan Collymore was an added attraction. The Villa manager clearly recognises Southgate's influence in the dressing room as well as sensing a chance to coax the best from the pounds 7m enigma he inherited.
On Saturday, Collymore gave his most committed display of the season, scoring twice in the defeat of Liverpool and enabling his new boss to savour the end of a hectic week. Gregory said: "When I got home I sat down with my wife and children and we had a Chinese take-away on the kitchen table. I told them: `It doesn't get any better than this'."
He will be delighted to be proved wrong in the Vicente Calderon Stadium. The events of the past seven days mean that the time he would normally have spent assessing Leicester's first-round conquerors has, of necessity, been condensed.
"I'm aware of Atletico's strengths and weaknesses," Gregory said. "Peter Withe [chief scout] has watched them twice and I've had half an hour with him. We've also got videos and dossiers, but I don't want to get weighed down with all that stuff. The most important thing is that we are properly organised."
Gregory added that he was tempted to retain the team who beat Liverpool, though the experienced Steve Staunton and Mark Draper are fit to return. Atletico, who came from 2-0 down to hold Espanyol on Saturday despite being reduced to 10 men, are without the suspended Radek Bejbl as well as the broken-leg victim Juninho.
Coached by the former Luton player, Raddy Antic, they will look to Christian Vieri, their pounds 12.5m striker from Juventus, to maintain the form that has brought him almost a goal per game.
Given the reputation of Atletico's president Jesus Gil for firing managers, few would have backed Antic to outlast Little this season. In fact, the Yugoslav is now in his third full campaign. His reputation has spread sufficiently for him to attract a respectable number of votes when Birmingham's evening paper asked readers to choose from 10 candidates for the Villa hot-seat (they did not, incidentally, include Gregory).
Gil and the Villa chairman, Doug Ellis, were reportedly dining together last night, perhaps waxing nostalgic about some of the aggregate of 43 managerial changes over which they have presided. The toast may well have been Ron Atkinson, who both men famously sacked. Gregory, meanwhile, was looking to the Atkinson era for inspiration, citing Villa's victory over Internazionale as an example to which his team should aspire.
Villa would arguably settle for the 2-1 defeat which Leicester suffered here, especially with the potentially precious away goal. Gregory conceded that it would take a brave performance to achieve an even better result, but believed that his new charges had "courage in abundance". Tonight they will need to show him that they also have class.
Atletico Madrid (probable; 4-4-2): Molina; Aguilera, Santi, Andrei, Toni; Caminero, Vizcaino, Paunovic, Pantic; Kiko, Vieri.
Aston Villa (probable; 3-4-3): Bosnich; Ehiogu, Southgate, Scimeca; Wright, Hendrie, Taylor, Grayson; Joachim, Collymore, Yorke.