Hey, don't get me wrong. I never said black people should have no reason to dislike the confederate flag, just that it has meaning to the people who fly it that has nothing to do with the reasons black people dislike it.
I mean, it might be comparable to the "White" House, which was built by slaves, worked by slaves, and only recently were black people elevated to positions near the top of the Executive Branch. We're talking until ~120 years after the Civil War was over! It's a travesty.
And you rightly point out overt racism (and worse) in a Northern state like Oregon, a state that never flew the Confederate flag. There have been lynchings in California, and Ohio, and Michigan and many other Northern states all along, as well.
I agree it may be highly questionable in this case (the bus driver), and I don't know him nor can I read his mind.
You ask yourself a question with a complex result. If the confederates had won the war...
Realize the Northeast Liberals of the time tired of the war quite early and favored calling and end to it with the confederates ultimately being another country. European nations were ready to establish traditional diplomatic and trade relations with the South.
The war wasn't going so well for the North when Lincoln freed the slaves - the battle of Gettysburg was fought in July of 1863, and the Proclamation was issued in January. Last time I looked at a map, Gettysburg was on Union soil, not on Southern soil.
The North wasn't exactly friendly to black people, either. I mentioned the lynchings, etc., but even being free meant poverty, terrible living conditions, etc. Except for the being free part, maybe worse conditions than for slaves. The North was lilly white, too - about 4.4M black people in all states combined, 488,000 of them "freemen" in all states combined.
The abolitionists weren't exactly friendly to black people. Most of their ideas I've read about weren't about freedom and citizenship, but about shipping black people off to someplace in Africa and other intellectually reasoned schemes.
Then there's after the war, when Jim Crow flourished in states in the South and the North. Here's a list of Jim Crow laws by state, from Wikipedia:
http://en.wikipedia.org/wiki/List_of_Jim_Crow_law_examples_by_State#California
Baseball was desegregated until 1947. The last two teams to have at least one black player were the Red Sox and the Yankees (Northern States). The military was desegregated in 1951. Schools desegregated in 1954. Black people disenfranchised from the voting right by poll taxes and the like until the 1960s.
More specifically to your question, the answer is that we can only speculate, and it really depends on what "winning the war" means. It could mean the confederacy was allowed to be a separate nation, or it could mean one country run by the South. Since the latter wasn't the South's objective, I'll speculate on the former.
For starters, the South was agrarian and would have suffered greatly from not having partner states who had strong industries. Maybe they'd look for a partner in Europe or even go back to being British colonies.
If that didn't happen, the pure economics of things would have likely led to abolition rather quickly anyhow. Consider it's cheaper to pay a guy $.10 a day and for him to have to figure out his own housing than it is to provide housing, food, etc., for slaves.
The whole Manifest Destiny thing would have devolved to both nations making land grabs in the West and likely continuous military confrontation.