Mission Driven

The 2006 Collegiate School alumna was one of 12 young people from several countries who participated in a management training program directed by the Sheik of Dubai, Mohammed bin Rashid al Maktoum, one of the largest owner/breeders of thoroughbred racehorses in the world.

 

Her odyssey took her to Ireland, England, Australia, Dubai, and, much closer to home, Kentucky. Her goal was to become credentialed as a bloodstock agent, an equine professional who buys and sells racehorses on commission.

 

“That’s what I was training to do,” she said. “That’s what I wanted to do.”

 

The voices in her head and heart ultimately directed her elsewhere, however.

 

“When the internship ended, I went to work in the industry,” she said. “When I was about 25, I realized that as much as I loved horse racing, I wanted to do more mission-driven work.”

 

Lillis had always enjoyed writing. At Collegiate, she penned several articles for the Match, then earned an undergraduate degree in English, and over the years, wrote numerous creative pieces, mostly for her own enjoyment.

 

She wasn’t sure where her avocation would take her, if anywhere.

 

“I always thought I was going to be the next great American novelist,” she said. “Instead, I wound up being a frustrated novelist masquerading as a journalist.”

 

Masquerading? Actually, no.

 

After paying her dues for several years, Lillis signed on with CNN in 2021 as a senior intelligence reporter.

 

Though her work now is high profile, her second career as a journalist began humbly with occasional freelance pieces for a racing publication called the Saratoga Special. In 2013, she joined the staff of Nautilus Magazine, whose editors, Sean and Joe Clancy, became invaluable mentors.

 

“They hired me as a marketing intern, but I wound up writing stories,” she said. “I leaned on my experience with the horse racing newspaper where I cut my teeth as a cub reporter. I learned how to cold call, walk up to people and ask questions, pay attention to the details, use my eyes and ears, and write what I saw.”

 

Lillis credits two of her Collegiate English teachers, John Coates and Dr. Roger Hailes, as mentors who ignited the literary spark.

 

“Both in different ways taught me how to read, which is a skill that teaches you how to write,” she said. “Nobody can write without being a reader. If you don’t learn how to read with attention and an understanding of the mechanics of the craft, how are you going to be able to do it for yourself?

 

“We read To Kill a Mockingbird [in Coates’s 8th grade class]. It was like he handed me a key to unlock endless treasures if I wanted to spend the time picking the lock. For years, I sent my own fiction back to him to [critique].”

 

“I could go on about Doc for hours. He was so, so good. He introduced me to James Joyce, who to this day remains one of my favorite writers. We did [A] Portrait [of the Artist as a Young Man].  He introduced us to [works] that, in the hands of a lesser teacher, high schoolers might read but aren’t ready for it. Doc was able to make Portrait accessible to 11th graders, which is a significant feat. We did [Joyce’s] ‘The Dead’ with him, which is still one of my favorite short stories of all time.”

 

Lillis’s time at Nautilus was a watershed experience.

 

“I was living in New York,” she said. “I was reading everything I could get my hands on. I’d discovered long-form journalism. I was supposed to be doing their Twitter account, but I was coming up with story ideas.

 

“I hit on this idea: Oh, wait, there is a way to exercise this sort of literary creative muscle that I have while telling true stories. It was the marriage of this mission-driven work that I was looking for with my creative ambitions. I wanted to tell stories that mattered.”

 

As she contracted freelance work and served as associate editor at Healthcare Dive, her future began to unfold.

“I didn’t have a journalism degree, so I wasn’t a very attractive candidate,” she said. “My résumé said horse racing. I was taking any job I could get just to get the clips.

“I managed to get hired in a low-level job at The Hill covering cybersecurity, which is hilarious because I did not know anything about cybersecurity or Congress, which is what The Hill covers, so I had a steep learning curve.

“I’d been there maybe a year when the hack of [Hillary] Clinton’s emails in the run-up to the 2016 election happened. It became my story. As we know now, there was Russian intelligence involvement, and cybersecurity became an intelligence story. That’s what set me on the path to being a national security reporter.

“I often tell young journalists: don’t close yourself off to a specific beat or pathway because the right story will potentially carry you on to a very good career on a larger beat. Be your best on whatever beat you’re on because you don’t know what opportunity that beat will present to you.”

From The Hill (where she met her husband Mike Lillis), she reported for Defense One, a subsidiary of The Atlantic, from 2018-2021. There, she covered national defense and security issues and once again found herself traveling the world.

She embedded with U.S. troops in Syria and accompanied them on patrol. Just after she landed, at 10 p.m., at a civilian airport adjacent to a military base in Erbil, in northern Iraq, to begin that assignment, she experienced a series of challenges, including a rocket attack launched by an Iran-based militant group.

“When I landed, they tried to deport me and put me on a plane back to Qatar,” she said. “I was trying to talk the Kurds out of sending me back, and the whole building shakes with this rocket attack. The plane took off, so they were stuck with me overnight. While I was in a holding cell in the airport, they let me keep my phone, and I was able to get the paperwork issues sorted out.

“In the meantime, all the entrances and exits from the airport had been closed down because of the rocket attack, so I was stuck there at two o’clock in the morning, and I speak none of the dialects. Then, these four stunningly attractive Australian men in civilian clothes came up to me and said, ‘M’am, are you American?’ I said, ‘I am.’

“They were Australian special forces that worked with the U.S. coalition. They hitched me a ride out of the airport and got me where I needed to go. It was a good adventure.”

While at Defense One, Lillis also filed reports from such hot spots as Afghanistan, where she traveled with Gen. Mark Milley, the Chairman of the Joint Chiefs of Staff, and Iraq, where she embedded with American troops.

“For a period of time,” she said, “I was all over the Middle East covering America’s wars.”

In January 2021, she was on a layover at Shannon Airport, in Ireland, enroute back to the U.S. with a military delegation when she received a call with a job offer from CNN.

So began yet another exhilarating, meaningful, and impactful adventure.

“Speaking and reporting for television is a completely different kettle of fish than writing for the web or for print,” she said. “I had to develop a whole new skill set [that would enable me to] condense a story down to a 60-second sound bite. That was a big challenge.”

In the three-plus years since, Lillis has reported in depth on weighty topics such as the origins of the COVID-19 pandemic, the US withdrawal from Afghanistan, and the wars in Ukraine and Gaza.

“My role is to figure out what U.S. intelligence thinks about X-Y-Z,” she said. “For example, what has the U.S. intelligence community learned about the potential Iranian involvement in the October 7 attack?

"Asking that kind of question and finding the answer is my job. The intelligence beat is one of the toughest in Washington because much of what the intelligence community does is classified. The role of journalism in covering the American intelligence community is a really important check on a very expensive part of what the US government does with your taxpayer dollars.

“There’re really only two forms of accountability for the intelligence community: one is the House and Senate intelligence committees. The second is journalists like me trying to understand what’s happening in terms of covert actions and what the intelligence community thinks that U.S. policy makers then base their assessments on.”

Her reports appear both on the CNN website and on the air.

“If I have a big story, I’m on air all day, every hour, on the hour,” she said. “If I’m working on the reporting phase of the story, I might spend a week or two just reporting and not write a word.

“Then I’ll spend a day or two writing, and then the story goes out. Some stories come together very quickly. I get a piece of information in the morning. I write the story. It goes out that night, and then I’m on television the next morning. It’s kind of a cycle: reporting, writing, then TV.

 “I’m not an anchor or a correspondent who gets up there and covers whatever the news of the day is but doesn’t necessarily generate a lot of independent reporting. I only go on television when there’s a specific story that I’m covering.”

Does she aspire to be an anchor?

“I actually don’t,” she said. “Being an anchor is a very hard job and a very different job. You’re not boots-on-the-ground, out on the street, creating your own reporting.

“There’s also generally not a lot of writing. Writing is really my first love. I love doing television, and I enjoy developing that skill, but my career is weighted toward reporting and writing with television as almost a supporting role.

“I still think of myself as sort of a small fish in a big pond. I’m lucky to do what I do. I like my job. I’m humbled by what I do because I think it’s important work.”
~Weldon Bradshaw