Ex-BHS director Dominic Chappell has been ordered to pay £50m to cover losses the firm incurred before its collapse.
A High Court judge said Mr Chappell tried to “plunder the BHS Group whenever possible” after he bought the company for £1 from Sir Phillip Green in 2015.
The ex-director was imprisoned for six years in 2020 over tax evasion.
He has since been sued by BHS liquidators FRP Advisory.
At a hearing on Tuesday, Mr Justice Leech said Mr Chappell never had a realistic plan to secure capital for the company when he acquired it.
The judge also said Mr Chappell “should make the payments” outlined, which includes £21.5m for wrongful trading.
He must also pay £17.5m for breach of fiduciary duty and other additional costs.
This takes the total to over £50m but Mr Chappell still faces another fine over a misfeasance or wrongful trading claim.
The amount he has to pay for that will be determined at a later date.
Mr Chappell gave a hand written note to the judge saying he had no legal counsel “due to lack of funds” and raised health and computer access concerns.
Mr Chappell is a former racing driver and had no retail experience when he bought BHS for £1 in March 2015.
The firm made headlines when it fell into administration with a billion pounds worth of trading liabilities and pension debts in 2016.
Just over a year into the new ownership the chain went under, resulting in 11,000 job losses and a £571m pensions shortfall.
Sir Philip Green was heavily criticised at the time for agreeing to the deal, and later agreed a £363m cash settlement with the Pensions Regulator to plug the gap in the pension scheme.
Earlier this month, two former BHS directors Lennart Henningson and Dominic Chandler were ordered to pay at least £18m to creditors over their role in the collapse of the retailer.
Robin Henry, partner and head of dispute resolution at Collyer Bristow, said: “The Court has clearly identified Chappell as the person who should take most of the blame for BHS’ losses.”