Tax guy here. Depreciation is a personal favorite of Trump (and most big businessmen). His tax reform included a provision allowing for 100% bonus depreciation, meaning that a business can essentially write off or expense 100% of the cost of an asset in the year of purchase rather than depreciate it over time, which is the whole concept of depreciation – to take the tax benefit over the useful life of the asset. There were already several mechanisms in the tax code for accelerating depreciation before Trump’s plan – section 179 depreciation and limited bonus depreciation. It is possible for big businesses to run consistent losses by expanding rapidly and expensing costs upfront – see Amazon’s $0 in tax paid for 2018.
All of that being said, I would expect to see some income being picked up somewhere here. Even in the 80s and 90s as his brand was expanding, Trump was not building enough to be writing off billions due to depreciation alone. His interest expense was high, meaning much of his operating cash was likely coming from loans and not actual operating income. I obviously have not seen all the details but this pattern of losses is indicative of a business with serious leverage and liquidity issues. There is a reason so many of the entities he was operating at this time were bankrupted.