Let's go to Tennessee, October 5, 2006. When Harold Ford was running for Senate, the TN Republican Party put out this mailer:
This was noteworthy because the Republicans darkened Ford up considerably. The first image below is the source image (from Ford's then-congressional website), the next one is a straight up conversion to black and white. The last is the photo that ran in the mailer.
At the time, state Democratic Party chair Bob Tuke's outrage was noted in the Knoxville News Sentinel:
They have darkened Harold Ford’s image to make a racist statement.
Now people can quibble whether Ford was darkened to make a racist statement, or whether he was darkened to be made "more sinister" (a difference without much distinction in my book), but clearly, the state Democratic Party chief had an appropriate reaction.
It says something ill of us as a society when darkening a person's features makes them look more sinister. And doing that to an African American (or Latino, or Arab, or other darker-skin people) is particularly egregious.
Some may want to explain it away as "business as usual". But in this case, that's not "business as usual" I'm willing to tolerate.