WASHINGTON — At nearly 6-foot-6, Tom Bossert is hard to miss. Yet he came and went through the gilded lobby at Trump Tower multiple times during the presidential transition largely unnoticed among the parade of White House job candidates headed for the elevators.
A Nov. 17 video from the lobby shows Trump adviser Dave Bossie twirling colleague Kellyanne Conway as Bossert looks on, generally ignored by reporters staking out the scene.
Bossert quickly caught the eye of the transition team, though, and then of Donald Trump. The president-elect offered Bossert the job of White House homeland security adviser nearly as soon as they met, on Dec. 22 at Trump’s Mar-a-Lago resort in Florida.
Bossert, with his smooth but unassuming manner, isn’t in the background anymore. He’s squarely out front as Trump’s details man on the hurricane recovery effort, a fitting follow-up to Bossert’s work helping write the “lessons learned” report after the Bush administration’s botched response to Hurricane Katrina.
His portfolio also includes the Equifax hack, counterterrorism, cybersecurity, flood insurance and more.
When Trump makes his first presidential visit to the U.N. General Assembly this coming week, Bossert is expected to be there as well.
Current and former White House aides say Bossert has been a bastion of competence in a White House riven by feuding, investigations and Trump’s unpredictable temper.
Trump has signaled his trust in Bossert by seeking his advice in private meetings and allowing him to speak for the administration in the most public of settings, from Sunday talk shows to the White House podium.
“I want to make sure you understand that you should continue to have confidence in what we’re doing as a government,” Bossert assured the nation from the briefing room on Aug. 31 as Texas reeled from the effects of Hurricane Harvey and Florida braced for Irma.
Polls show wide swaths of Americans have concerns about Trump’s presidency. But Bossert was determined to send the message that when it comes to handling hurricanes, the administration is on it.
At another briefing, Bossert was open about his intentions, offering reporters an atypical preface for such White House sessions: “I like to try to categorize my thoughts into informing, influencing and inspiring, if I can.”
Bossert got his start in Washington — and his subsequent invitation to Trump Tower — courtesy of David Bossie, who hired him fresh from the University of Pittsburgh when Bossie was chief investigator on the House Oversight and Government Reform Committee in the 1990s. The committee launched investigations into an assortment of then-President Bill Clinton’s activities, including his campaign finances.
When Trump won the presidency, Bossie says he immediately called Bossert to try to lure him back to the White House.
“There was simply no one else who could even come close” to being as qualified, Bossie recalls.
The 42-year-old Bossert, a fly-casting enthusiast, is regarded as a human briefing book for a president famously averse to the nitty-gritty, an expert in even the most mundane-sounding matters that make up the post-9/11 discipline known as homeland security. He’s figured out how to communicate with Trump — and Vice President Mike Pence and others — in ways the new administration values as it has confronted its first major natural disasters.
He also seems acutely aware that it doesn’t pay to attract more attention than the boss in the cauldron that is the Trump White House. Bossert declined an interview request for this story.
“Tom’s got a very good ability to read people” and deliver information in ways tailored to their styles, said President George W. Bush’s homeland security adviser Fran Townsend, who worked with Bossert in that administration. “I think that we see real differences in the way that, for example, that the president and vice president process information. … Tom’s got a strong relationship with both of them.”
For Bossert, politics is perhaps more challenging than details. He has gotten some blowback when asked how he lines up with Trump’s approaches to racial violence and climate change.
Asked on CNN’s “State of the Union” about the confrontations in Charlottesville, Virginia, Bossert at first repeated Trump’s language that “both sides” were responsible for what led to the death of one person. Pressed, he specifically condemned white supremacists.
Later, from the White House podium, Bossert declined to say whether man-made climate change might be responsible for multiple historic hurricanes. He promised an analysis on the subject at a later date.
“The politics is way outside my lane,” Bossert said.
Bossert “is more candid sometimes than a politician and more open than any of the politicians I know,” said Stewart Baker, a lawyer who worked at the Department of Homeland Security while Bossert served Bush. “That’s going to be an issue. Does he really want to do what people in political positions have to do?”
Bossert got his law degree in 2003, but by then the Sept. 11, 2001 attacks had claimed the life of a friend and former colleague — Barbara Olson, chief investigative counsel for the House committee where Bossert worked.
On the 16th anniversary of the attacks this year, Bossert said from the White House podium that 9/11 was the reason he’s in the homeland security business, though he did not mention Olson.
“Tom was affected just like the rest of us were, that Barbara Olson was on the plane,” said Bossie.
In the Bush White House, Bossert dove into the many disciplines that make up what’s now known as homeland security — cybersecurity, counterterrorism and general emergency preparedness. Eventually, he served as Bush’s deputy homeland security adviser.
When President Barack Obama took over, Bossert founded a risk management business in Arlington, Virginia.
Josh Corman of the Atlantic Council, where Bossert did a fellowship on cybersecurity, said the president’s adviser can keep up with the more subtle and obscure parts of the field that Trump has called, “the cyber.”
“Tom’s role covers three things: homeland security, counterterrorism and cybersecurity. Every predecessor in that role has treated those as separate domains, Tom uniquely understood the intersection,” Corman said. “There are only maybe only five people in the whole government who understand that, and he’s one.”
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