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.”)
Another official familiar with the dynamic said high-level DHS staffers viewed it as their job “to manage Stephen so that the secretary could try to focus his or her time on the work that they needed to be doing. If you do not keep Stephen happy, then he goes straight to the president and creates more problems. I think we all saw it as a necessary part of the job, but not something that anybody enjoyed.”
Whereas Kelly, Nielsen, and McAleenan had résumés that allowed them to stand up to the White House and Miller, albeit to varying degrees, Wolf does not. He lacks the same level of experience applicable to running a sprawling patchwork of a department encompassing everything from the Coast Guard to Immigration and Customs Enforcement (ICE). Critics point to the Portland fiasco as evidence of his knowledge gaps. (Wolf has repeatedly defended the department’s response.) “If it were a different administration and you served as chief of staff for two years, you would have had the experience” necessary to run the department, a former official said. “This was not a normal administration. The secretary’s focus was like 90% wall and immigration, then 10% was the leftover. [Wolf] missed out on what you might assume a chief of staff would have observed.” Depending on your perspective, these failings could be winning characteristics. Wolf, said one source, is “malleable to the president’s views because he [doesn’t] have the background and experience to be able to push back.”
Wolf’s tenure has been dotted with additional controversies. In early September, Brian Murphy, the former head of the Department of Homeland Security’s intelligence division, filed a whistleblower complaint accusing Wolf and other top agency officials of pressuring him to whitewash threats from white supremacy and Russian election interference. (During congressional testimony, Wolf dismissed the complaint as “patently false” and a “fabrication.”) He also came under scrutiny after NBC News reported that the consulting firm where his wife works received millions of dollars in federal contracts from DHS. (Wolf told lawmakers he plays no role in procurements.) A series of recent moves—including a major ICE raid in California, a new policy to expedite deportations, and a highly unusual billboard campaign in the swing state of Pennsylvania—have drawn criticism that DHS is being used to boost Trump’s reelection prospects in the final stretch of the presidential campaign.
Insiders are quick to separate the 240,000 rank-and-file DHS employees from the politicization at the top. The sentiment among many in the department, sources say, is a readiness to turn the page on the Trump era, with the hope of a Joe Biden presidency on the horizon. “Nobody’s excited that he’s their leader,” one said. “Everybody’s just kind of ready to move on to somebody that they could be proud to serve.”
Outside of the department, among veterans of DHS, concerns abound as to the impact of Wolf’s Jekyll/Hyde act. “If a law enforcement, security, or intelligence organization is viewed as a part of an instrument of partisan politics, then the public loses confidence in that organization,” Cohen explained. “The department has an important mission.… And if the department is not focusing on [that] core mission because the president and his top advisers in the White House view the department as an instrument of its political agenda, then America is less safe.”
What game Wolf might be playing now is unclear. With the sun potentially setting on the Trump administration, his total buy-in now, of all times, seems curious. Some have speculated he has stylings to run for office in Texas—though whether tying oneself to Trump is a viable choice in future election cycles remains to be seen. As he has for so long, Wolf remains inscrutable to many who worked closely with him. “If it came out that that was his design, my instinct is that doesn’t surprise me,” said one former colleague. “There is something about him that is a lack of genuineness and there’s a strategy always at work.”
— Progressives Are Going Rogue to Flip Pennsylvania for Biden
— White House Reporters Fume Over Team Trump’s “Reckless” COVID Response
— Why Anti–Trump Attack Ads Might Actually Be Helping Him
— Tax Mess Aside, Can Trump Pay Off His $1 Billion in Debt?
— News Media Begins to Contemplate a Post–Trump White House
— The Kimberly Guilfoyle Sexual Harassment Allegations Get Even Darker
— As Trump Falters, Democrats See an Expanding 2020 Senate Map
— From the Archive: Inside Trump’s Twisted, Epic Battle for Mar-a-Lago
— Not a subscriber? Join Vanity Fair to receive full access to VF.com and the complete online archive now.