Jonathan France's deception enabled him to fund a fleet of Aston Martins, Ferarris, a Rolls Royce and a McLaren.
The former Wakefield scrap metal dealer was also able to buy a five-bedroom house in Huddersfield, spend almost Â£200,000 on high-end furniture and splash out Â£70,000 on fine wines.
France, 46, was helped in his deception by two of his motor racing pals who helped him ignore disqualification restrictions and continued to run companies, while diverting millions of pounds from them.
France, Jody Firth, 37, and Graham Schofield, 53, were jailed for a combined total of 18 years today at Leeds Crown Court.
The court heard how France was first disqualified from being a director of limited companies for 14 years in 2004 for his role in the mismanagement of Eric France and Son (Metals) Limited which went into insolvency.
He was then declared bankrupt in November 2008 as he was unable to pay more than Â£7m owed after the collapse of his sole-trader businesses Embassy Racing and EFS Group.
Being bankrupt and disqualified should have limited his ability to directly or indirectly run a company.
But France ignored the restrictions and continued to run companies.
He also diverted millions of pounds from company accounts to a combination of other business and personal accounts so that he could buy a house, luxury items and a fleet of cars.
With the help of Schofield, he misled the trustees managing his affairs, claiming he had no assets to pay back his debts.
Just under Â£7m in assets has since been recovered by the trustee in bankruptcy.
Months before he was made bankrupt in 2008 on the grounds that he had no money to pay his debts, France deliberately transferred close to Â£180,000 worth of money and assets out of his personal estate to avoid paying his creditors.
The money and assets went to Schofield and Firth, friends he had made through motor-racing.
Assets moved included two classic cars worth Â£27,000 to Schofield and Firth.
A further Â£152,607 was transferred to bank accounts controlled by Schofield.
France then began a sustained campaign to continue running companies despite having restrictions placed on him.
With Schofield, he also engineered false and misleading explanations to the trustees and the official receiver about a substantial amount of possessions.
Between 2008 and 2013, France managed and controlled JKL (Wakefield) Ltd before the company went into insolvent liquidation.
The company bought and sold metals and listed Firth as the company director.
France repeated the same tactic when Schofield had his name down as the official director for two racing companies effectively controlled by Jonathan France.
The firms - WFR Ltd and WFR Holdings Ltd - ran between 2011 and 2014 before also going into liquidation.
France, of The Paddocks, Flockton, Wakefield, pleaded guilty to four counts of fraudulently transferring property, three counts of acting as a director while bankrupt, as well as one count each for failing to disclose property to the official receiver or trustee, perjury, fraudulent trading, false accounting and money laundering.
He was jailed for ten years.
Firth, of Oakenshaw Lane, Wakefield pleaded guilty to money laundering and helping Jonathan France run a company despite being a bankrupt.
He was sentenced to five years, four months.
Schofield, of St Pauls Road, Mirfield, pleaded guilty to money laundering and was jailed for two and a half years.