Massive losses on your tax return do not mean you are losing money. Things like depreciation, interest, charitable donations, etc all make you look like you lost money and in real estate, which is Trump's business, you can accumulate massive depreciation of assets if you choose. From an accounting perspective, everything Trump said in his debate was correct. His debt ratios are off the charts good and his companies are very far from in trouble. The fact Hilary was arguing about how much money he owes was either blatant stupidity on her part or exploitation of the ignorance of the audience. It's really sad to see these lies perpetuated in mainstream media showing it also falls into one of those two categories. Any accountant that was listening would have to agree..