It was Paul Lambert; the former Celtic and Scotland midfielder having been identified as the very man Flynn wanted in charge of the team when his Lionheart Consortium finalised their purchase of the West Lothian club in 2005.
There was just one problem; Lambert was set on gaining his coaching qualifications in Germany, a spell playing with Borussia Dortmund having already rewarded him with a Champions League winner's medal. "A thing you're going to see is Paul is very single-minded," said Flynn, speaking more than eight years on and with Lambert now preparing his Aston Villa team for a crucial encounter with Manchester City this evening. "He told me, 'look Pearse, I want to go and do my coaching in Germany.' No-one else wants to go to Germany. He did."
The Irishman ceded to Lambert's will and moved on. Two managers, 12 months and a narrow relegation escape later, he returned to the Scot. It had been hard work – Allan Preston and Richard Gough had both come and gone – but Flynn finally had his man and his reign could really get going. Instead, it brought disaster for Livingston on the pitch.
Lambert took charge of 26 league games. He won just two. His tenure would be pockmarked by 18 defeats and he would resign after just eight months, with Livingston marooned at the bottom of the table. Now back in the business world, Flynn is self-effacing about his spell at the helm of the West Lothian club and he can admit to his own mistakes as much as those of the managers he employed. Among them was Lambert's choice of assistant manager.
"Paul just made one mistake I think when he was at Livingston," said Flynn. "He brought in as his assistant his best friend, Norrie McWhirter. The worst thing you can have in management is people agreeing with you all the time because you're the boss. I think Paul needed somebody to say, 'wait a second'. Norrie was a great guy, but I think it was a mistake."
It might seem a costly one for Lambert given his reign but Flynn was still left with the impression of a manager with real promise. The Irishman will have felt a sense of vindication, then, when Lambert was appointed by Villa in June having enjoyed relative success in charge of Wycombe Wanderers, Colchester United and Norwich City. "I remember giving him a reference to go to Wycombe [his next job after leaving Livingston], and it was all about the character and the individual," said Flynn.
"I couldn't go on and say about us riding fifth in the league or whatever, so it was all about the strength of his character and I think he's been proven. Now he's back in a tough spot with Aston Villa and I've got no doubt he'll get out of it."
His belief might appear misplaced given Villa's woeful form – the club are just four points off the bottom of the Barclays Premier League – but Flynn knows that Lambert's best work is not accounted for in a league table. "Paul would make the toast, Paul would muck in, Paul never gave the impression that 'I've got a Champions League medal and I played for Celtic and Scotland.' Never," he said. "Paul was prepared to give up his own salary – which was modest at best – to give a player some more money or get another person in. That's the way he was.
"He's a particular type of man who's going to do well. He's got that mix of being humble, yet has a strength of character. I remember one time listening to him in the dressing room; we were playing in the semi-final of the League Cup, we lost and he was going nuts. So he's not afraid to put it around."
Flynn is perplexed by football managers and still finds it hard to understand their successes and failures at various clubs. Yet there is the sense that in Lambert he found someone he could judge, and with conviction. "I think you need to look at the manager as you do in business," he added. "If he's taking the same guys and he's making them 20% better then that's the manager."
"[At Livingston] it was too early in his career to do that. But, in my time at the club, he was the best manager Robert Snodgrass had. He got the most out of him. Every single one of our managers, with the exception of Paul Lambert, wanted to get rid of Snodgrass. I was watching him thinking 'Jesus, he's the best player we have'. Now he's playing in the Premier League in England with Norwich City. I think Snodgrass was Paul's best achievement."
It would be obscured by a series of heavy league losses and embarrassing cup exists to lower division sides, though. Those results have been echoed during his time at Villa and some might consider that history is now repeating itself for Lambert. Flynn has faith in the Scot but he is less convinced that a move to Villa Park was the right one.
"I was surprised he took the Aston Villa job," he said. "He was adored at Norwich and they've got a great support. Okay, it's not as big as Aston Villa, but Aston Villa will be . . . it'll be a tough one for Paul. I don't think avoiding relegation will keep the fans happy."
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