Creditors are demanding to know the whereabouts of some paintings of the world-famous Drambuie Collection – purchased by Malcolm Scott in 2006.
The Sunday Herald can also reveal that Scott's parents have been financially ruined after trying to underwrite their son's debts.
Until late last year, Scott was the Scottish Tory treasurer and the UK party's most generous contributor from north of the Border.
The flamboyant Edinburgh tycoon donated at least £1.6 million to the Tories and allowed Prime Minister David Cameron and Foreign Secretary William Hague the use of his private jet.
However, the Old Fettesian's fortune, based on grain and property interests, hit the skids after he failed to repay millions borrowed from banks. His companies were put into administration and he was sequestrated.
His creditors have since demanded to know what he spent his fortune on, as well as what happened to his assets.
This newspaper can reveal that Scott, through one of his companies, bought part of one of the biggest corporate art collections in Britain six years ago.
The Drambuie Collection was put together over 20 years by the famous drinks company, but a cost-cutting drive meant it had to be put under the hammer.
The sale, conducted by Lyon & Turnbull, included more than 450 lots and went for about £3.1m.
Some of the purchases during the two-day sale included £220,000 for Peploe's A Still Life Of Pink Roses And Fruit, £140,000 for John Linnell's Storm In Autumn, and £110,000 for Robert Gemmell Hutchison's The Village Carnival. An 18th-century glass called the Leith Goblet reportedly fetched £11,000.
It is not known which elements of the collection Scott purchased, but it is believed he spent close to £250,000.
Questions are now being asked about where these paintings are located, as part of a broader probe into Scott's spending.
The fallen businessman's nine-bedroom mansion in Kirknewton cost £1.85m, and it is believed he also spent up to £2m on landscaping the property.
He also shelled out £706,000 on a retreat in Elie, Fife while spending millions of dollars on his beloved jet.
An administrator's report into his firms also reveals an investigation was launched into the location of two missing rugs worth nearly £50,000.
Meanwhile, Scott's 74 year old mother, Florence, was sequestrated last week after trying to help with her son's debts.
The elderly woman had given a £10m "personal guarantee" to one of her son's creditors in January.
Her sequestration was granted at a hearing at Edinburgh Sheriff Court on Wednesday.
Scott's 76-year-old father, David ,was also made bankrupt earlier this year after giving an identical £10m guarantee.
Labour MP Graeme Morrice said: "Malcolm Scott must be open and transparent about what happened to his art collection. And, given that this man was Scottish Tory treasurer, Ruth Davidson should be asking questions about his financial stewardship of the party."
A spokesman for KPMG, which is handling the administration process, said: "KPMG is not able to comment due to the ongoing nature of its investigations."
Scott could not be contacted for comment.
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