When Chad Wolf defended the Department of Homeland Security’s crackdown in Portland, Oregon this summer, his former colleagues were perplexed. To them, the man decrying the “violent anarchists” threatening “to burn down” a federal courthouse was almost unrecognizable. It wasn’t just the partisan nature of his comments, made before the Senate in August, but the aggression with which he delivered them. “That doesn’t match the guy I worked with,” a former senior DHS official told me. “It’s not his personality.” Wolf, like so many others before him, was plainly putting on a show for Donald Trump: “He’s playing to the audience of one.”
Wolf’s movements in the months since federal officers in unmarked vans hoovered up protesters in Portland have constituted an encore performance, featuring rhetoric that could’ve been cribbed from the president’s Twitter feed. As experts fret that the presidential election, less than two weeks away, might foment widespread violence regardless of the outcome, Wolf’s acquiescence to Trump has arguably become a homeland security threat in itself. “There’s a difference between advancing your political agenda and interfering in the ability of intelligence, law enforcement, and security agencies to protect the nation,” John Cohen, a former deputy undersecretary for intelligence and analysis at DHS, told me. “And that’s the difference here.”
Ask a half dozen people who have worked closely with Wolf to describe him—which I did—and the portrait that emerges is remarkably unremarkable. Sources I spoke with described Wolf as an effective but milquetoast bureaucrat who, before his elevation to the helm of DHS, kept his personal views so close to the vest that at times he didn’t appear to have any. “He’s a nice guy, but not a super-nice guy,” said one source who worked closely with Wolf. His stoicism often prompted colleagues to ask, “What’s Chad thinking?” said a second former senior DHS official. (After repeated requests from Vanity Fair, DHS did not make Wolf available for an interview.) As he fell further upward through the ranks at DHS, Wolf’s survival instinct led him to foster connections with those who would hone him into the tool he has become. “He is savvy in the sense that Chad knows who is important around the president and who he needs to not piss off. Namely, Stephen Miller,” the second former senior DHS official told me. “Stephen Miller is the key to understanding Chad’s rise in this administration and his ultimate nomination to be secretary of Homeland Security by the president.”
Wolf didn’t climb the institutional ladder so much as hang from a rung longer than most. After a four-month stint at the Transportation Security Administration in the beginning of the Trump administration, Wolf joined the DHS front office as deputy chief of staff and top aide to then deputy secretary Elaine Duke. He stuck by Duke when she was elevated to acting secretary as a result of John Kelly and Kirstjen Nielsen taking White House positions. When Nielsen returned to DHS and was confirmed as secretary, Wolf remained in the same role, serving as her chief of staff. After Kevin McAleenan took over from Nielsen, Wolf was confirmed as the undersecretary for strategy, policy, and plans.
When McAleenan left, Wolf was one of just a handful of DHS officials believed to be eligible to fill the leadership void from a legal perspective, given the agency’s hollowed-out ranks. He certainly wasn’t the president’s first choice, or even his second. The bombastic Ken Cuccinelli and Mark Morgan fell higher on the list but were ineligible. Ultimately, as a former senior administration official put it, Wolf “was available and less likely to disagree with White House direction.” So, he stepped into the secretary role in an acting capacity last November. In August, Trump finally announced his plan to nominate Wolf to serve permanently. He still hasn’t been confirmed by the Senate, and a federal judge recently ruled that Wolf was likely serving as secretary illegally.
Whereas Nielsen developed a reputation for having sharp elbows in her role as John Kelly’s gatekeeper—an assessment likely undergirded with sexism—Wolf’s approach was more procedural. Another source who worked closely with Wolf in his chief of staff capacity said he acted as a guide through the Trumpian ecosystem for his principals. He could provide “a situational awareness of what other stakeholders might be thinking” and “information about how a person’s gonna react to a policy position”—a valuable skill in any administration, but particularly in Trump’s. “Some of these DHS issues are so volatile and so complex that…the probability of making anyone happy is pretty low,” this person said. “You have to decide what the agenda is. And I think that there’s a short game and a long game to a strategy.”
The longer he stuck around, the more crucial a game piece Wolf became for Miller, whose desire to micromanage U.S. immigration policy is well documented—even if, as I’ve previously reported, the senior White House adviser actively tries not to leave a paper trail of his influence. Sources familiar with their dynamic told me Wolf and Miller would sometimes speak multiple times per day, dating back to Wolf’s early days in the front office. And while the first source who worked with Wolf recalled Wolf complaining about his frequent communications with Miller, he clearly recognized the importance of the relationship, both for himself and for his principals. “Stephen really tried to be the shadow secretary of Homeland Security, and his vessel for doing that was Chad Wolf,” said the second former senior DHS official. But, this person added, “Chad was not a rubber stamp for Stephen.” Wolf found ways to break with the White House on certain issues, depending on the behest of either Nielsen or Duke. Still, in the words of this former official, “Chad walked that tight rope with Stephen and got in his good graces.” (Miller previously said in statement to the Washington Post, “Chad is faithfully committed to executing the president’s bold vision of an immigration policy that prioritizes the interests of U.S. workers, wage-earners, taxpayers, and communities.”)