The current celebration is that he has lost billions and is one of the worst business people ever. This is a great talking point, in that it demonstrates that he is a fraud and a loser.
But a small caution is to point out that it is a point of pride for corrupt, rich people to try and avoid paying taxes at all (see, “taxes are for little people”, Leona Helmsley). This is done through generating excessively large expenses so that the overall result is a loss. And if those expenses are paid indirectly to yourself, then you can keep all the profit instead of paying any taxes.
Another way of saying this: having terrible looking taxes (big losses!!! every year!!!) is a requirement if you are cheating the system out of taxes you should be paying.
Consider this example: If you have revenues of $1 billion from a casino and expenses of $800,000,000, you have a profit of $200,000,000. If the tax rate is 35%, you owe $70,000,000 to the government, leaving you with $130,000,000 profit.
What if you create fake expenses of $300,000,000 by paying other companies (maybe offshore) that you just happen to own? You now have revenue = $1 billion and expenses of $1.1 billion = a loss of $100,000,000. What a loser right? Can’t make money from casino!!
Actual profit in this case is the full $200,000,000 because no taxes are paid. Also, there is additional profit from the fact that the “loss” can be carried over and used to not pay taxes in the future. Additionally, there is an extra $100,000,000 paid out from the casino to someone (money laundering anyone?)
What would a tax history look like for someone who followed this strategy for decades? Billions in losses over time, big losses most years and carryover losses sheltering the years when income is positive. What has the NYTimes shown us? Exactly this pattern.
So I would urge caution on interpreting whether there were actually losses from any of these businesses. There is certainly suspicious tax avoidance as the numbers look exactly as they would if your number one goal was not to pay a dime to the government.
On the optics, however, flame away: Loser! Broke! World’s worst businessperson!