Two years before bankruptcy

 A transfer of a debtor's property made within two years before the filing of the bankruptcy petition (or other time limit set by state law) for which the debtor received little or no consideration while the debtor was (or was rendered) insolvent. Fraudulent conveyances also include transfers made with actual intent to hinder, delay, or defraud creditors.

https://content.next.westlaw.com/practical-law/document/Ibb09e990ef0511e28578f7ccc38dcbee/Fraudulent-Conveyance?transitionType=Default&contextData=%28sc.Default%29?

This is why he needs to consult a bankruptcy lawyer.