That history is why an exchange Trump had with Fox News's Bill O'Reilly on Tuesday night prompted a heavily negative response.
O'Reilly was asking Trump to weigh in on the sense of racial tension that has been pervasive over the past week, after the police shootings of two black men in Louisiana and Minnesota and after the killing of five police officers by a black man in Dallas.
The interview began with O'Reilly asking how Trump might heal racial divides in the United States, to which Trump replied that the country needs to improve its "spirit." That led to this back-and-forth.
O'REILLY: There [are] still some black Americans who believe that the system is biased against them, the American system — because they're black, they don't get the same kind of shot, they don't get the same kind of fairness that whites do. What do you say to them?TRUMP: Well, I have been saying even against me the system is rigged when I ran as a, you know, for president, I mean, I could see what was going on with the system, and the system is rigged.O'REILLY: Yes, but that's not going to lift anybody's spirits.TRUMP: We have to fight.O'REILLY: If you go out and say the system is rigged, that's not going to lift their spirits.TRUMP: No, what I'm saying is they are not necessarily wrong. I mean, there are certain people where, unfortunately, that comes into play. I'm not saying that. And I can relate it really very much to myself.O'REILLY: I have to refocus you, though, on the African American experience. All right? Do you think you understand the African American experience? Do you think you understand it?TRUMP: Well, I would like to say yes, but you really can't unless you are African American. You can't truly understand what's going on unless you are African American. I would like to say yes, however.O'REILLY: All right. If that's true, I agree with you.
The deal with Trump, as we have learned by now, is that he speaks off the cuff. This is unusual for a national politician, and it has been advantageous for Trump, allowing him to simultaneously say what he thinks and have an out for those occasions when he says something with which people take offense. So a generous reading of the bolded quotes above is that Trump understands that the African American experience in the United States is unique ("you really can't unless you are African American") and that he understands that the system is stacked against black Americans. ("I have been saying ... the system is rigged.")
But this overlaps with Trump's other habit when he speaks: He likes to talk about himself. So to explain how the system is rigged against black Americans, he uses an example that's close to his heart: The system was also rigged against him.
It's worth a quick aside here to note that the system was not rigged against Trump as he ran for president. He started making this argument after it appeared that he might end up with fewer delegates in Louisiana than Ted Cruz (because Cruz outworked him in reaching out to unpledged delegates) and when he got swept in Colorado (because Cruz outworked him there, too). But in most states, Trump got far more than his share of delegates in state contests, because the Republican system had built-in bonuses (such as winner-take-all triggers) that Trump was able to enjoy. Yes, the Republican establishment wanted him to lose, and members of the establishment moved what levers they could to try to get him to lose, but it turned out that they didn't have that many levers. Saying the "system" was "rigged" depends a lot on how you define "system" and "rigged."
Which is precisely why Trump's analogizing between his electoral travails (his ultimately successful electoral travails) and the existence of institutionalized racism was so tone-deaf. Trump's "system" was "a few people who hold power in the Republican Party." The "rigging" was "weird rules on delegate allocation." For black Americans, the "system" is American society and its institutions of power. The "rigging" is the after-effects of centuries of explicit racism and the continued existence of implicit racism.
Those things are not the same.
By any standard, as even the candidate himself likes to boast, Trump has been successful. He didn't overcome a rigged system to become rich and famous. His wealth and his fame are a natural extension of a system that he entered in a privileged position. So while Trump — like all Americans — has experienced moments of unfairness (subjectively, certainly, and maybe objectively), that's not only obviously different than battling a rigged system, it is inherently different. Unfair moments and a system constructed around being unfair in several obvious and subtle ways are not things that are commensurate.
Again, a gracious reading of Trump's comments is that he's trying to say that he gets that this unfairness exists, which is itself contentious in our current political conversation. And to demonstrate that understanding, he seizes on an example he has at hand.
In drawing that analogy, though, he demonstrated one of the main points of disconnection between black and white Americans. A white American who is treated unfairly — say, by not getting as many delegates as he thought he should have — is still a white American in an America where being white still holds distinct, ingrained advantages. White Americans would like to say that we can understand the African American experience, but "you can't truly understand what's going on unless you are African American."
A point on which Trump is absolutely correct.