"They can't get out their own half, why don't they get some big kid who can boot it up into their area, and play from there?" Certainly that tactic would have been more productive, especially at a low-quality youth level, and on a bumpy pitch.
"They don't play that way here, even if it means getting beat. They need to learn early to pass it through the team and move into space to receive the ball," I replied.
Passing, movement, control under pressure, pace, patience. This is modern football. Does Scotland play this game? Honestly? Not even close.
For that reason, in 2002, I realised that I would likely never see Scotland in a World Cup finals again. It is why I placed a bet on Scotland finishing bottom of this group.
The Como conversation was the first episode that flashed back to me on Tuesday evening after witnessing a brutal humiliation. The second dates back 12 years to the last game against Belgium in 2000. Scotland led 2-0 at half-time against 10 men, but incredibly proceeded to blow the lead in the next 45 minutes. I attended that match with my Italian wife and she saw the reaction in the VIP suite afterwards. "Why are they smiling and eating their pies? Why is the president not running down the dressing room to sack people on the spot? You have just lost your chance to qualify. People need to pay. Does nobody care?"
Positive thinking is always good, and admirable. But there is a point where "glass-half-full" becomes a credibility killer. Levein's early September statement: "We are capable of winning all 10 games", surely falls into that category, betraying unforgivable naivety, or rank incompetence.
But the real challenge for Scottish football is to distance itself from personality-led blame and salvation because there is no solution in that direction. And it is not really Levein's fault that Scottish, and UK football, has a culturally different recipe.
There will be gnashing of teeth this week. Public kickings will be delivered. And the Scottish Football Association board will deal with the fallout. Look out for this phrase in the coming days: "Craig should be judged on what he is doing with the new technical director [Mark] Wotte on the long-term solutions."
The long-term solutions? In my experience, most organisations fail due to reasons of culture, not resources or determination. The world merely passes them by and they remain in the past.
I would contend that the culture of Scottish football is outdated and very, very wrong, and there should be comprehensive answers to the following provocations.
The premise is simple: the home nations have not really competed at world level in 50 years, despite having the richest football economy in the world and attracting the game's greatest talents. It is clear that British teams are technically inferior, dreadfully static in movement and are unimaginative.
The pace of the game has increased; just look at the speed of any game from the '70s. That time on the ball is unthinkable these days and British teams are lost.
l Has the teaching in the UK of the technical and tactical necessities of the modern game kept up? Is there emphasis on the correct attributes of the modern game? Do too many teams still pick the biggest and strongest boys in the youth teams, then find out that advantage is transient? I believe the thinking and teaching in Largs is modern and relevant. I believe Jose Mourinho.
l Does the UK laddish and drinking culture, especially in football, negatively affect the development of what are to be professional athletes? Would such attitude and behaviours be tolerated in any other elite sport preparation? Swimming, for example. One can't help but think that a talent like Charlie Adam (choose your own wasted talent; they are plentiful) may have done better had he been brought up somewhere like Belgium.
l Does the football fan culture in the UK which demands constant, incident-packed, high-impact, goalmouth action discourage thoughtful and patient possession and tactical development? Is it all right to just "get it intae the box"?
l Is there a show-me-your medals inverted snobbery, where purveyors of an outdated culture still dominate and prevent the fresh air of new ideas? How many managers in Scotland have not been former players? Or inversely, how many managers in Scotland have no playing record, but have a profile like Mourinho, Andre Villas Boas or Andrea Stramaccioni, the coach of Internazionale?
l What are Celtic doing at youth level that apparently allows them to compete with the top international teams at ProGen under-19 level? What can be learned? Does the SFA's Mr Wotte agree?
These are questions that should be answered by respected people such as Andy Roxburgh, who is the foremost technical and tactical expert in UEFA. Oh, I forgot, the fans and media never liked him.
*Jim Goodwin believes Scotland supporters need to be "a bit more realistic" as calls grow for manager Craig Levein to be replaced. The St Mirren midfielder is from Waterford in the Republic of Ireland but as the son-in-law of Mick Oliver, Levein's chief scout, and having lived in this country for two different spells totalling seven years, he takes a keen interest in the fortunes of the Scottish national team. He looked at Scotland's World Cup qualifying draw and felt that Levein's side would do well to finish fourth.
"I do hurt when Scotland lose and I've a great interest in how they are getting on," he said. "With my father-in-law being involved I know how hard they are all working to get it right. I know what goes on behind the scenes and it's very disappointing how it's gone because it doesn't reflect well on the Scottish game.
"But the players need to take a hell of a lot of responsibility too. And I think Scottish fans need to be a bit more realistic if I'm truthful. Belgium are fantastic, so are Croatia, and Serbia are better than Scotland, too. I would have expected Scotland to finish fourth, in all seriousness. But I'm disappointed because Craig Levein is a very good man and I hope he gets time to turn it around. Whether he is or not, remains to be seen though."
Goodwin felt criticism of the Scotland team following the 2-1 defeat to Wales last Friday night was unfair. "If they'd gone 2-0 up through Steven Fletcher it was game over," he added, refererring to the header that was disallowed. "I know the early results haven't helped. If they'd won one and drawn one then four points going to Cardiff is a different prospect and it could have been a different story."
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