The 2014 World Cup qualifiers are the crossroads for Levein. If he pulls off the spectacular triumph of taking Scotland to the finals in Brazil he would savour every minute of it and then, almost certainly, leave for a more lucrative club job in England. Anything less than that would amount to a second failed qualifying campaign and, inescapably, a P45.
He looked calm and collected enough about all of this at the Scotland squad hotel yesterday. Levein has always invested enormous faith in the central group of players he relies upon the most, and he lavished further dollops of praise on them on the eve of this afternoon's opener against Serbia. Group A looks as relentlessly awkward today as it did when it was drawn 13 months ago. There is not a truly outstanding team in the section, nor a lamb-to-the-slaughter, either. Four of the contestants – Scotland, the Serbs, Belgium and Wales – are within seven places of each other in the latest FIFA world rankings.
Given the likelihood of such fierce competitiveness it was put to Levein that failing to claim six points against the Serbs and Macedonians at home over the next four days would amount to the death knell for Scotland's prospects. "That's a bit short-sighted, is it not?" he asked. "I know it's been said, but not by anybody who know what they're talking about.
"We have 10 games to play and we want to win every single match. That's how it works. All I can do is do the job to the best of my ability and try my hardest to learn as I go along. I feel I am in a better place than I was two years ago. The players are better individually and collectively. They understand the system, they have more international and club experience and the atmosphere within the group is 100 times better than what it was. All of that leads me to believe we are better than we were two years ago.
"That's where my confidence comes from. I'll get judged on results. If you had asked me two years ago if the group we had then could win every game in our campaign I would have hesitated and been a little unsure. I think we have a squad now capable of that. 'Can we do it' is the question.
"I believe 100% in the group of players we have. I desperately want to go to Brazil and I have learned so much in the last two years about this job, about my players and about other international teams. I am a much better international manager now than I was two years ago.
"The players have earned my respect over the last two years by gradually improving their own personal performances and improving the performances of the team.
"I've got huge confidence in them. We're in such a different place now than we were two years ago, when I was just in the job and didn't really know what I had or what system to play."
The difficulty many supporters will have with Levein's hugely positive assessment of the scene is that he was saying much the same things during the Euro 2012 qualifiers, and Scotland's results fell far, far short of the necessary standard. Only one point was taken from the 12 available from the group's two best opponents, Spain and the Czech Republic. Two more were spilled against a poor Lithuania and even beating little Liechtenstein at Hampden required a goal so deep into stoppage time the floodlights were about to be switched off for the night.
This campaign has to be different. Serbia have a back four in which each defender is over 6ft tall and has been valued at – either in transfers or unsuccessful bids – more than £10m. Kenny Miller and Jordan Rhodes – both are likely to play part of the game – have to find a way through them. Big creative performances will be needed from Charlie Adam and Steven Naismith. Robert Snodgrass and James Morrison who will have to deliver powerful, driving displays.
Alan Hutton and Paul Dixon, a pair of full-backs more comfortable going forward than back, need to step up. Andy Webster and Christophe Berra too often look vulnerable against bruising, physical forwards who offer Serbia plenty of bulk. The Serbs have a number of towering players to flood into the Scotland box at set-pieces. That challenge will have to be met.
Scotland aren't likely to prevail without a solid contribution from the captain-for-the-day, Gary Caldwell. It was six-and-a-half years ago that Caldwell made his debut in a 5-0 defeat against France in Paris. Today, via a subsequent match in which he was the unlikely winning goalscorer against the French, he will pull on the shirt for the 50th time.
"I'm thrilled to bits for Gary," said Levein. "I didn't get anywhere near 50 caps. It was a struggle to get to 16 so I know how difficult it is to get into the Scotland team. To play 50 times is a huge achievement.
"I liken him to Darren Fletcher in terms of his influence on the rest of the players, the example he sets off the field and how professional he is in every single training session and match. He is a strong character, his values are ones that I admire, and I can't pay him any greater compliment than likening him to Darren. Those two are hugely important players. If guys like Gary Caldwell don't get to play at a World Cup it would be a travesty."
Today is hard to call. The Serbs have one win in their last 10 matches and failed to score in seven of them. Yet the suspicion remains that this will be about the Serbs' strong defenders against Scotland's bright attackers. And, at the other end, Serbia's non-scoring forwards against Scotland's unconvincing back four.
A Scotland win by single goal, then? Hampden would take that in a heartbeat.
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