The petitioner occasionally made loans to friends, acquaintances and business associates, doing so 12 times over a six-year period without the normal formalities associated with a lending business. He did not hold himself out as in the business of lending money and did not keep business records that were close to adequate, and did not perform "due diligence" with respect to any loans that he made. He made a loan to a construction company which failed to pay its $925,000 loan upon it becoming due in 2007. The company filed for reorganization bankruptcy in 2008 showing assets of over $62 million and liabilities of over $34 million. The petitioner did not file a claim in the bankruptcy. Ultimately, the case was converted to Chapter 7 from Chapter 11. The petitioner filed an amended return claiming a business bad debt deduction (ordinary loss deductible on debt that becomes partially worthless) on the 2008 return. The petitioner argued that if the loss wasn't deductible in 2008, it was in 2009. The court held that the loan would not qualify as a business bad debt, but that any bad debt would be a non-business bad debt (deductible as a short-term capital loss in the year in which the debt becomes wholly worthless). The court determined that the plaintiff had failed to show that the debt was completely worthless in either 2008 or 2009. Instead, the court pointed out that the petitioner first acted as if the debt was worthless in 2010 when he filed his amended 2008 return. The company's filing of bankruptcy that year was insufficient to show that the debt was worthless in 2008 because it was not clear at that time that the company was insolvent. Cooper v. Comr., T.C. Memo. 2015-191.