“Whether any of his political ﬁxes or ﬁnancial remedies would work, I couldn’t say.” wrote Milloy of Barry’s lunch interview. “But it did sound like he had found a solution to the problem of alcoholism and drug addiction. And what he had to say about a spiritual path to freedom from the bondage of self was a lifesaver.”
That may have been the closest Milloy would ever come to seeing Barry and himself in the same light. Barry had started his career as a pugnacious activist. Some of those Milloy associated with, like Nnamdi, were involved with the black power movement back in the day. But Milloy never quite took on black nationalist politics.
By the late 1970s, Milloy’s beat had shifted from Prince George’s County into the District, and he gained a reputation for knowing its streets better than anyone else. In 1981, when the veracity of a Pulitzer Prize-winning story by Janet Cooke came into question, editors turned to Milloy for help. Cooke, another young, black reporter, had embarrassed the Barry administration with “Jimmy’s World,” a tale of an 8-year-old heroin addict, adrift in the District with no intervention from the authorities. (Barry, hoping to save some face, claimed the boy was known to the city and was receiving treatment.) Inside the Post, some staffers were skeptical of the whole thing. After Cooke won the Pulitzer, former colleagues of hers in Toledo, Ohio, noticed details of her own official biography didn’t match up with what they remembered. Milloy knew all the dark and dangerous places Cooke’s story referred to. “I was asked to go with her to find Jimmy,” he says. When Milloy escorted Cooke to the spots she’d identfied, there was no sign of the drug-addled kid. She’d made him up. Milloy wasn’t surprised: “I just thought it was far-fetched.”
If the Cooke ﬁasco created any tense racial dynamics, Milloy was insulated. “Most of my immediate editors over the early days were black,” he remembers. “They answered to white people. When I was angry at them I called them middlemen”—he laughs—“operating for the man. But that wasn’t true. That was just my emotional stuff. The fact is I have worked for some of the best editors in the business, and for the most part they were black editors.”
No matter how good they were, Milloy’s black editors found it hard to move up, though. “It’s weird to think that all the time that I’ve been there, there’s never been a black managing editor or a black executive editor,” Milloy says. “And there are complicated reasons for it, but it just hadn’t been the case.”
Being a black columnist at the paper has its own strangeness, especially nowadays, when anger has become a commodity. “In this day and age when page views and comments are, you know, very appealing to advertisers, is that a good thing or a bad thing for people to be [angry]?” Milloy says. “I get disturbed because the reality is a person who makes a comment and calls me a nigger, that’s still an ad man’s click.”
As a reporter, Milloy had often channeled his own observations on race and class into his work. He would, as he puts it, “ﬁght for the cause” in print, even if he never explicitly got into more political forms of engagement. As his career took off at the Post, that was a problem. The features he wrote were saturated with opinion. After wrestling with Milloy’s penchant for spouting off, editor Larry Kramer came up with a solution in 1983.
“So he’d wrangle over each feature I wrote trying to ﬁgure out what it was,” Milloy says. “One day, he decided to make life easier on everybody by dropping the disclaimer, making the byline bigger and just calling me a columnist.”
The Metro section columnist mantle Milloy snatched up brought him into contact with the District in a whole new way. Whereas the reporter is the city’s messenger, the columnist is its oracle, expected to convey truths in ﬁts of revelatory ranting. For Milloy, this has meant writing in a jazzy voice that harkens back to a time when such agreeable stylistics might be accompanied by two congas and some incense.
Other columns showcased Milloy’s inner shock jock. In July 1993, he proposed that while attempting to combat AIDS, the city was lending more support to gays and whites than to (presumably straight) blacks. In 1996, he framed D.C.’s steep black homicide rate as white-run genocide. In September 2002, when Anthony Williams was mayor, Milloy accused the black politician of not being able to relate to other black people. And in 2007, Milloy shellacked Fenty for hiring whites as the city’s legal counsel and attorney general.