White House whistleblower makes case for political dissent at Winston Center virtual event

Miles Taylor, smiling younger white man in a button-up shirt and black plazer

Miles Taylor, former Homeland Security chief of staff, spoke at Winston Center virtual event on Feb. 18.

Americans are “too afraid to be wrong,” and ours is “the culture that breeds tyranny.” So warned Miles Taylor, the former Trump administration official behind a controversial 2018 New York Times op-ed criticizing the then-President from within, at a virtual live event hosted by the Winston Center for Leadership and Ethics at the Carroll School of Management on February 18. 

In his talk, titled “Why Dissent Matters—Lessons on Leadership Culture from a White House Whistleblower,” the former Homeland Security official echoed many of the moral and ethical concerns he raised as the anonymous author of the Times op-ed, titled “I Am Part of the Resistance Inside the Trump Administration,” as well as A Warning, the 2019 bestselling exposé that followed. This time, of course, Taylor put a name and face to the claims. 

Addressing an audience of 215 attendees over Zoom from Naples, Florida, against a backdrop of patio furniture and a setting sun, Taylor described Trump as a President who bred chaos. He likened the Oval Office to “a New York bagel shop, with Trump barking orders and patrons going in and out.” And he depicted the Department of Homeland Security, where Taylor served for more than half of Trump’s term in office, as a place where career officials scrambled day and night to thwart an onslaught of destructive policies coming from the White House. 

Some such demands—to “build a moat with alligators at the southern border,” or to tear-gas as well as "electrify, or shoot migrants” as they crossed from Mexico—they were able to stamp out, Taylor said. Others, however—such as family separation—were carried out anyway. (The latter he called “egregious and disgusting,” and said he regrets not resigning as soon as it began.)

Needless to say, officials and supporters of the former administration have often returned the fire. For example, former White House press secretary Kayleigh McEnany has dismissed Taylor as a “low-level, disgruntled former staffer” as well as a “coward who chose anonymity over action and leaking over leading.” The Trump administration also denied some of the specific allegations leveled by Taylor and other dissenting officials.

Taylor’s talk at the Winston event was more than just a tell-all, though. Citing former Presidents Theodore Roosevelt and Dwight D. Eisenhower, Taylor made a more academic case for why public dissent is a necessary and healthy part of a functioning democracy. While Trump often attacked dissenters to dangerous ends, “we are in charge of democracy,” Taylor argued, referring to the American people. He pointed to the nation’s divided public discourse—our unwillingness to engage with opposing ideas in a genuine search for the truth—as the real risk to our democratic institutions. “Washington is not broken,” he said. “We are broken.”

Cover of book by Anonymous, later revealed to be Miles Taylor

Taylor anonymously authored "A Warning" about his experiences in the Trump Administration.

A lifelong Republican, Taylor did eventually resign from his role as chief of staff at DHS in the summer of 2019, shortly after Kirstjen Nielsen, Trump’s third secretary of that department, was ousted. Since then, Taylor has been an active voice for reform within the Republican Party. Beyond his book and frequent media appearances, Taylor is co-founder of the Republican Political Alliance for Integrity and Reform (REPAIR), a group of current and former Republican officials who opposed Trump’s reelection and are working to amend the damage they believe he’s done to their party. In a brief question-and-answer session following his talk, Taylor hinted at “big announcements” from his group in the coming weeks regarding the future direction of the G.O.P. 

The Winston Center runs several different speaker series throughout the year, all of which feature prominent voices on the subject of ethical leadership. These events have carried on virtually over the last year. They are central to advancing the center’s mission of engaging students, faculty, and staff at Boston College in continued dialogue about ethical issues at the intersection of business and society.

Another Winston Center program that has shifted to a virtual format is the Jenks Leadership Program, a three-semester leadership training curriculum for Boston College students of all majors. The program has two concurrent cohorts enrolled this spring; one recently launched with a successful virtual retreat, and the second is working toward completion of their final service projects, all of which focus on this year’s theme of “Love and Inclusion at BC.” 

The Feb. 18 event was presented in collaboration with the Political Science Department at Morrissey College of Arts and Sciences. It was hosted by the Winston Center’s director, Monetta Edwards, and moderated by Marc Landy, professor of Political Science and faculty chair of the Boston College Irish Institute. 

Leslie Ganson, Carroll School News