While managing JKL (Wakefield), Jonathan France diverted more than £6m from the company accounts to a combination of other business and personal accounts.
Items bought included a five-bedroom house in Huddersfield, while just under £200,000 was spent on furniture and £70,000 was used to buy fine wines.
And around £1.8 million was also used to purchase a fleet of high-end vehicles and personalised number plates, including three Aston Martins, two Ferraris, as well as a Rolls Royce and McLaren.
France’s deception included falsifying company cheques, invoices and other paperwork to make it appear as if payments had been to bona fides creditors of the company when in fact they were made to purchase the cars and luxury goods.
France repeatedly failed to properly disclose his property to the trustees, he was twice privately examined at Huddersfield County Court in 2012.
At court, Jonathan France repeatedly and falsely argued that he had sold various items of jewellery, including two Rolexes and a platinum ring, as well as a number of paintings to a colleague for £250,000.
Deputy Chief Investigation Officer, John Fitzsimmons, of the Insolvency Service, said: “Jonathan France is a fraudster and lied in order to cover up his true activities and fund his opulent lifestyle.
“But it wasn’t just him who carried out the deception as he was supported along the way by Schofield and Firth, two racing colleagues who were well aware of France’s bankruptcy.
“We will always seek to tackle those who flagrantly disregard and cynically abuse the insolvency regime, which is there to protect creditors. After a substantial investigation we are pleased to see that France, Schofield and Firth have received significant prison terms.”