The former Gers manager's job was made even harder with Martin O'Neill at the height of his powers having returned Celtic to domestic domination in Scotland and about to guide the Hoops all the way to the UEFA Cup Final.
But Big Eck's Ibrox trophy haul of seven pieces of silverware, including one domestic treble, while also making the Light Blues the first Scottish club to reach the last 16 of the Champions League in season 2005/06, is one that still commands real respect among the red, white and blue legions.
Current Rangers manager Ally McCoist may not have had the managerial experience that McLeish picked up at Motherwell and Hibs before his arrival in Govan, but Eck believes Coisty's four years as No.2 to Walter Smith have more than equipped his former Scotland team-mate to guide Gers back up the Scottish football ladder.
Now watching from afar in his new role as Nottingham Forest gaffer, McLeish has looked on with increasing admiration at the job being done in the Ibrox hot seat by McCoist, who has now guided his youthful side 19 points clear in Division Three at the halfway stage of the basement championship.
And Eck has no doubt that while the structure of the Scottish league game may change, as long as Coisty can produce consecutive promotions, Rangers will re-emerge at the summit of the Scottish game with a manager who is more than capable of matching his success at the club.
McLeish said: "It has not surprised me particularly that it has taken time for Rangers to really gel and start to perform with the consistency you would expect of them results wise.
"I remember back to my period as manager of Rangers and at different times we lost some very influential players and I would look around and expect some understanding and there would be none.
"That is because the bottom line at a club of that stature is that whoever pulls on that light blue jersey is expected to deliver victory. But you look at the quality of players that have left Rangers in the wake of all the financial problems and it was always going to be tough to regain or develop any momentum immediately.
"But Ally has got things going and now you look at the SFL3 table and Rangers are 19 points clear and I bet that over the first half of the season Coisty has just learned so much and that will be invaluable to him.
"If Ally can take Rangers to consecutive promotions, whatever the league set-up is, then by the time he gets them back to the top tier he will have amassed so much experience that he will have improved vastly as Rangers manager. So this could work out very well for both Ally and Rangers.
"He may not have had the chance to learn the job at other clubs, but he is learning it at Rangers and that is a unique position for a Rangers manager to be in."
Looking back at Gers stuttering start to the basement campaign, which saw McCoist's men fail to win away from home until they secured a 2-0 success at Clyde, on the last Sunday in October, McLeish believes this was an inevitable part of the growing-up process for the youngsters McCoist was forced to blood. Big Eck said: "What has been really important for Rangers is that at the beginning when they were struggling to get the wins on the road they were still winning at home.
"The confidence that all the youngsters such as your McKays, Macleods, Crawfords and the like would have got from winning at Ibrox has ultimately led them to turn the corner away from home.
"It has also been about them coming to terms with the culture shock of playing in the basement and learning to deal with all the tricks that the old pros use to school kids. But they have come through all of that and as a group they will be the better for it."
With Gers skipper Lee McCulloch crocked McLeish has no doubt the likes of Lee Wallace, who wore the captain's armband against Berwick, has a key leadership role to fulfil.
THE former Rangers and Scotland manager said: "The injury to McCulloch has been unfortunate as he has been outstanding for up front and at the back and he is clearly a huge influence in the dressing-room as well as on the field of play.
"Clearly Rangers are short on experience and the likes of Lee Wallace, Neil Alexander and Ian Black all have big roles to play while McCulloch is out. But Rangers are only going to get stronger from here on in."