The one-time Rangers manager was back on his old stomping ground yesterday and found himself, for whatever reason, drifting back to November 2004 and the sight of that most formidable Croat, Dado Prso, white bandage protecting a wounded forehead, launching himself at a Fernando Ricksen free-kick and scoring the goal which laid the foundations for a 2-0 win over Celtic and the second of his Premier League title wins at the helm.
Often the most meaningful flashbacks are not the most obvious.
Amid the memories, though, there has been a creeping sense of unease accompanying McLeish's most recent visits to this personal field of dreams. He speaks of the "doom and gloom" he felt when watching Rangers' recent William Hill Scottish Cup semi-final loss to Dundee United and remains horrified by the findings of the club's recent business review, which revealed Rangers have somehow managed to burn their way through the best part of £70m in two years.
It is those figures, laid down in black and white, that make him fear most for the future. Chief among his concerns is that Ibrox Stadium will end up being owned by someone other than the club should the kind of financial meltdown that dragged the business into liquidation two years ago happen again.
That is why McLeish has thrown his weight behind Dave King, the former Rangers director bidding to alter the powerbase inside Ibrox and ask the current board to give the Union of Fans supporters' group the security on the stadium in return for the release of season-ticket money.
Statements issued last night have merely heightened tensions between the South Africa-based businessman and those in the boardroom as this stand-off over ticket revenue grows more entrenched.
However, McLeish remains clear. The former manager believes that King, a multi-millionaire and known supporter, is the solution to Rangers' multitude of problems and that preserving the status quo will only intensify the deep misgivings within the fanbase over just how well-protected assets such as the stadium really are.
"I have concerns that Rangers wouldn't own it," said McLeish, speaking at an event to support the Tesco Bank Football Challenge, a nationwide participation programme for schoolchildren. "Maybe I'm just talking like a traditionalist here, but that would be unthinkable.
"Maybe people will say: 'Big Yin, you don't know what the finances are all about.' They might think it's better it's not owned, that it might keep the costs down or whatever.
"The same goes for the training ground. There was a massive investment in that a few years ago. If you were to lose assets like that, that would scare me."
Rangers have stated unequivocally that they will not give security over the stadium to the trust fund being operated by King and the Union of Fans, but McLeish believes they should acquiesce.
"It seems to be the balance," said McLeish. "Does anybody else not think that? I know there will be different opinions, but it just seems like common sense."
The 55-year-old, who won seven trophies for Rangers during his spell as manager between December 2001 and May 2007, believes there is a mutual trust that exists between King and the supporters.
That cannot be said of the relationship that exists between the present members of the board and the club's following. McLeish feels that is why a pathway must be found for King to re-enter the citadel in a position of power.
"I think it would be good to see someone like Dave come in because the trust of the fans and the respect of the fans is a given," he said.
"I don't want to criticise anybody who is already here. It's easy to criticise from outside when you don't know exactly what's going on. Somebody has to run it. I can only take Dave at face value and from what I've read in the papers, what he's saying. We have to trust that and the fans have to trust that.
"It sounds as though there is a bit of responsibility being handed to the fans and you know that they will go to war to save this club. That's probably one of the strong points of the club surviving."
Despite the off-field chaos, Ally McCoist, the Rangers manager, is already looking at new players for next season, with 34-year-old Kenny Miller having been approached about a third spell at Ibrox following his departure from Major League Soccer side Vancouver Whitecaps.
"Kenny is a fit guy," said McLeish, who worked with the striker during his time as Scotland manager. "When your legs go, your legs go. Sometimes, the last person to see that is the individual, but Kenny has played to a good level in the MLS. I feel he would do a job."
Of course, Rangers are announcing redundancies in other areas of the business while protecting McCoist's playing budget, but McLeish insists the manager cannot allow himself to be caught up in the emotions running high around the club right now. "He's got to just focus on his job and hope the powers above him are working to get Rangers above water again," he added. "He won't be here otherwise."