Alex McLeish guided Rangers to a Treble in 2003 then watched his trophy-laden squad crumble in a summer of out-of-contract chaos.
This time next year – the 20th anniversary of that domestic clean sweep – he’d hate to think current Ibrox boss Gio van Bronckhorst will have to face the same massive rebuild.
Which is why McLeish believes the Dutchman will have some serious soul-searching ahead of him with Ryan Kent, Joe Aribo and Alfredo Morelos free agents next summer.
If they don’t sign extended deals they’ll need to be sold to ward off the spectre of losing the trio for nothing.
McLeish believes the situation is a massive headache for Van Bronckhorst, who already faces the prospect of losing Calvin Bassey – albeit for a massive fee if the club takes advantage of the Nigeria international being on a long-term contract.
But Aribo, Kent and Morelos will see their value in the transfer market disappear if they don’t re-sign.
A year from now that trio – who could net the club more than £30million if they were sold with a couple of years still on their deals – will head for pastures new.
And that has given McLeish unwanted flashbacks to the summer when he lost Arthur Numan, Barry Ferguson, Claudio Caniggia, Lorenzo Amoruso, Neil McCann and Bert Konterman – some of whom were sold but with most leaving on Bosmans.
McLeish was forced into a frantic few weeks of wheeling and dealing in the free transfer market and while some of the arrivals had been genuine quality in their heyday – Frank de Boer, Emerson, Nuno Capucho, Egil Ostenstad, and Henning Berg – they were well past their peak and made little impact.
And Rangers went from Treble winners to finishing second in the league the following season, losing their grip on the Scottish Cup at the quarter-final stage and going out of the League Cup in the last four.
Eck doesn’t want to see Van Bronckhorst wrestle with the same difficulties but appreciates the dilemma the current gaffer and the number crunchers at the top of the marble staircase have in the coming weeks and months.
Commenting on the possibility of the star trio running down the deals, McLeish said: “It’s a huge decision and it would be really tough to take if they left for nothing next year.
“It was like me at the end of that season, losing seven or eight players and you’ve got a month to go before pre-season training starts and you are trying to regenerate the squad.
“You end up with free transfers coming in. Guys who have been great players but are maybe not at the peak of their careers any more. That’s hugely difficult, and as I say, that’s when the recruitment has to be great because the budget was downsizing and at Rangers you still have to play and be at a level the fans expect.
“A lot of Rangers players have been touted for big, big money and would fill the coffers up greatly. But can you get a replacement?
“I would definitely be trying to get them to extend because it will take so much money to replace them with similar quality.
“The difficulty in this world is they will all be wanting to play in a better league and that’s no disrespect to our fantastic country.
“But it’s the Scottish league and if an English Premier League side comes in, their ears prick up.
“If someone comes in with the right offer, it will be hard even for Rangers or Celtic to turn down.”
McLeish believes Van Bronckhorst will have to look Morelos, Kent and Aribo in their eyes – and Bassey for that matter – to determine if their focus will be 100 per cent on Rangers if they stay next season.
He added: “Every week in England, I am asked about Bassey. Is he going, is this one or that one going?
“The prices that are now being touted are astronomical and it’s credit to Rangers and the players for getting to the level they are playing at. They’ve raised the bar and raised the fees.
“But if the players are staying, they have to be fully committed. I am sure they’ve come to Rangers and been flabbergasted at the level of that club and their status in the world as a club.
“A lot of them would want to stay for that reason but at the end of the day, if there’s an opportunity to play in the richest and best league in the world, then it will be hard to stop some of them leaving.
“And them dragging their contracts out is the worst nightmare for the manager. Yet, if they leave at the end of their contracts but have a spectacular final season, do you think maybe it was worth it?”
The other side of the coin, of course, is that by selling an asset or two, cash will be freed up to allow Van Bronckhorst to put his own stamp on the team that he inherited from Steven Gerrard.
McLeish added: “If Gio has a black book of potential players, which I’m sure he will have, I’m sure they won’t come cheap and will be of high quality.
“He will want to bring the same level of quality, or better, that he has managed this season.”
