It seems to me that since the late 1990s and early 2000s, structural and personal racism in American culture have gotten significantly worse, undoing much of the progress that was achieved from the 60s through the 90s. Representation of people of color in popular culture has declined, and the criminalization of blacks through the War on Drugs was accelerated by the advent of “broken windows” policing. The War on Terror exacerbated the problem, leading to racial profiling and a situation where the majority of people of color portrayed in the media were either domestic criminals or foreign terrorists. Meanwhile, Islam was racialized in a much more intensive way. The same administration that demonized Muslim countries could display criminal neglect of the black victims of Hurricane Katrina, whom the mainstream media shamed as looters and savages.
Paranoia surrounding Barack Obama, a black man with Muslim heritage, brought together both of these racist threads. His presidency was widely viewed as showing that we lived in a “post-racial” society, but the practical effect was to intensify the racist paranoia of a non-trivial portion of the population — it was as though their worst fears had come true. Obama himself is studiously centrist in all of his policy proposals and has consistently been eager to make a deal with Republicans at almost any price, but racially-driven hatred of Obama and a desire to deprive him of any achievements or legitimacy have led them to refuse to take yes for an answer almost constantly.
On the grassroots level, a growing movement of people who are literally protesting against state-sponsored random murder of blacks has faced an uphill battle for recognition and legitimacy in the public sphere, as the criminalization and demonization of black men leaves the majority of whites still giving the police the benefit of the doubt.
Thoughts? Am I being naive about previous eras? Are there some signs of progress that I’m missing?
An und für sich 
One way of tracking racism would be wealth disparity, particularly housing. The recent financial crisis exacerbated many of those problems. Blacks were specifically targeted by predatory lenders and as Paula Chakravartty and Denise Ferreira da Silva argue, words like “subprime” became racialized signifiers for bad subaltern debtors. This article argues that the financial crisis has devastated black wealth with no recovery in sight. We tend to focus on income disparity, but housing wealth has been the primary means of attaining middle class status in the US. Wall Street has taken that possibility away from the black community. This chart tracks the period you’re framing in the post.
The only substantive sign of progress (as you put it) that I’m wondering about is in the workplace. On the one hand, the macro-level employment picture seems to be as skewed along racial lines as ever. But inside individual workplaces, has the contemporary regime of procedures, trainings and so forth focused on “diversity” and anti-discrimination goals moved the needle? Are the demographics of employees at various levels at least somewhat less White? Do people of color report any decrease in experiencing a racist environment or actions where they work?