The liberal establishment’s third and perhaps biggest blunder in dealing with the legacy of Jim Crow isn’t tied to the failings of any one particular program, like busing or affirmative action. It’s a systematic problem, one rooted deep in the dysfunctional relationship between Black America and the American left. 

I first recognized this particular issue while researching racial integration in the advertising industry, which—as Mad Men viewers can attest—was far from a rousing success. The industry today is only marginally better than it was in Don Draper’s era. Starting in 1999, I spent eight years in advertising, working at five different agencies, and I can count the Black people I worked with on one hand. The industry’s racial disparities are so bad that in 2008, the NAACP announced something it called the Madison Avenue Project, a full-court legal assault on the industry to improve its hiring, promotion, and retention of minority professionals. Cyrus Mehri, the civil rights attorney best known for crafting the NFL’s famous “Rooney Rule,” signed on to help lead the crusade. In its story on the launch of the Madison Avenue Project, USA Today called advertising “a poster child for the death of diversity.” Mehri and the NAACP cited a wide range of culprits for this state of affairs—everything from bias in HR policies to broader socioeconomic barriers that keep lower-income minority hires from getting within a mile of the industry’s front door—but they left out one of the most obvious ones: the persistence of a separate and unequal Black advertising industry, sanctioned and sponsored by the U.S. government. It’s harder to bring minority talent in when minority talent is being paid to stay out. 

In 1969, when the Nixon administration launched its flotilla of affirmative-action programs, one of the president’s signature efforts was the Office of Minority Business Enterprise, which made small-business loans available to Black- and Hispanic-owned businesses, created vehicles for private equity groups to invest in those businesses, and carved out quotas and set-asides in federal procurement contracts to support them. White-owned companies that bid on government projects—for an ad campaign for military recruiting, for example—were now required to subcontract a certain percentage of their business to Black-owned companies, in the interest of sharing the pie. Thanks to the efforts of Reverend Jesse Jackson and Operation PUSH, this practice soon evolved beyond mere legal obligation to become a standard tactic for good racial PR. Black-owned Ford dealerships, Black-owned McDonald’s franchises, Black-owned Coke distributors, all followed from the drive to bolster Black ownership and entrepreneurship. During the ’70s and ’80s, this policy allowed Black-owned ad agencies not only to survive but to create a parallel industry of their own, earning hundreds of millions of dollars and bolstering the Black media landscape of Ebony, BET, and urban radio.

But the result of these set-asides was two forms of affirmative action working against each other. Here’s how it played out in advertising: Under government and public duress to integrate their workforces, white agencies (or “general market” agencies, as they’re often called) launched a wave of minority hiring that had an immediate impact, taking the rate of Black employment in the industry from a rate of practically zero in 1965 to 3.5 percent in 1970. However, since those same White agencies were now required to subcontract projects out the door to minority agencies, their incentive to bring Black hires in was significantly diminished. The rationale that Black agencies used to justify their business model was that they were more qualified to speak to Black consumers, which in turn cemented the stereotype that White people were more qualified to speak to White consumers. Culturally, legally, and economically, the industry settled into a pattern which ensured that “White” advertising happened over here and “Black” advertising happened over there. White agencies did little more than token hiring and recruiting.