If the losses are real, it is legitimate to deduct the loss. End of story. The income tax is about taxing income.
If the narrative is that he likely has not paid any federal taxes since then
(or little taxes), then that doesn't matter. It likely won't be seen that way. Are people really going to be like,
"wow, Trump's terrible business decisions cost him almost a billion dollars, and he was rewarded by not having to pay taxes for almost a quarter of his life. Yup, he earned that! Nothing wrong with this!"There is nothing "right" about Trump's life. He just takes and takes and takes whenever possible, even if it means taking the food out of small business owners mouths.