So what I want to know is whether or not this is that unusual for someone in real estate.

The discussion on r/politics is myopic and the discussion on /r/tax lacks detail.

From the NYT article:

The numbers show that in 1985, Mr. Trump reported losses of $46.1 million from his core businesses — largely casinos, hotels and retail space in apartment buildings. They continued to lose money every year, totaling $1.17 billion in losses for the decade.

Trump's statement/tweet:

“You always wanted to show losses for tax purposes....almost all real estate developers did – and often re-negotiate with banks, it was sport,

Now my very limited understanding of real estate and taxes is this:

• You can depreciate the building but not the land
• Depreciation can be carried over multiple years
• When you sell property you can roll those proceeds into the purchase of another property, thus delaying income tax

Are those accurate? If so, do they explain Trump's taxes?

I'm thinking not (I suspect Russian money laundering is the real source of income). However, I have yet to read a good discussion of the specifics. Has anyone read such a discussion or have insight to add?

Main story from NYT:
https://www.nytimes.com/interactive/2019/05/07/us/politics/donald-trump-taxes.html?action=click&module=Top%20Stories&pgtype=Homepage

CNBC's article about Trump's response:
https://www.cnbc.com/2019/05/08/trump-defends-tax-tactics-after-nyt-story-says-he-racked-up-more-than-1-billion-in-losses-it-was-sport.html

EDIT: As an aside, I got into a wee bit of trouble because my wife's (very) small business lost money three years running. The accountant that I worked with informed me that if a business losses $ three years in a row, the IRS considers it a "hobby" and you can't subtract those losses from your personal taxes. Is that in play with Trump at all? If not, why not?

EDIT2: I'm going to answer my own question I think. I heard a good segment on NPR yesterday that addressed my question. You can read the transcript here: https://www.npr.org/2019/05/08/721552462/president-trump-defends-himself-against-report-he-did-not-pay-taxes-for-8-years

The bottom line is it's not so unusual but it doesn't exclude the possibility of him running his businesses poorly either. So I think it's not really what the headlines have made it out to be.

In 2016, I was an ardent supporter of Bernie. But come the general, I voted 3rd party, because I was "Bernie or Bust." Many people accuse me of indirectly voting for Trump, allowing "the worst thing ever" to happen (esp since I'm in a swing state that went Trump). But here's the truth as I see it: Voting Democrat regardless of candidate, with their only qualification being "Not Trump," will only increase the USA's slide (deeper) into fascism.

The reality I see is that even if Trump had never entered the 2016 race, 90%+ of the policy, judicial appointments, and everything else that he has done since being elected would be identical no matter which "R" candidate won the race, because all of these things are exactly what the GOP has been doing for decades. In that regard, I consider Trump more favorable than any other R candidate, because he is at least failing to do his "real" job: Hiding fascist, imperialist policy behind a charismatic smile and some clever words.

Ultimately, this is the reason why I don't generally support Democrats either. Hillary's policy wouldn't have been as immediately destructive as the GOP agenda, but it also would not have stopped the march towards fascism. I voted my conscious in 2016, and will do so again in 2020. I just hope there are more people willing to do the same this time around.

I like to picture that the government of the USA is digging a hole. With every shovelful, we're sliding ever closer to a fully authoritarian fascist regime, and the destruction of our planet. While Trump (and the GOP as a whole) has been calling in for backhoes and drills to speed the process....as far as I can tell, only two candidates in the 2020 primary are calling to stop the digging: Elizabeth Warren and Bernie Sanders. At best, the other candidates are conveying messages akin to: "We need to compromise with the GOP and maybe slow down the rate at which we allow new backhoes to be brought to the pit."

In my mind then, it makes more sense for 4 more years of Trump, than to allow another center-right candidate for his opposition. Because at least Trump isn't able to pull off the charismatic smile and/or intelligent language that the Regan's, Bush's, Clinton's, and Obama's of the world have that allow terrible things to continue behind a cloak of "incremental change." It wakes up those who would otherwise tolerate these horrendous acts, and perhaps inspires them to become more active. By allowing for the political discourse to end with "Anything is better than Trump", it just permits the overall platform to gradually, but continually shift to the right.

And in my mind, it is the total death of real, dissenting voices in public discourse that is far, far worse than Trump winning another term could ever be.

I would love to hear if anybody else in this community has had feelings akin to what I've described here, as I've only been described as "insane" by most of the people I've discussed this with in person.

The one thing people didn't learn regarding Trump and is repeating itself with AOC.

When you consider a politician stupid, it actually empowers them to be crafty. I think Trump would love for you to think he is stupid.

When you constantly attack a politician, you actually give them more followers. It's strange, but the Streisand Effect is real, especially in this Internet era.

The biggest weapon in someone's arsenal is to actually just talk about what they are for. Not attack their opponent and give them press. The rules have changed.