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Silhouettes profiles Holly Gregory

Holly Gregory

From Silhouettes, by Tiffany Razzano
Originally published Jan. 20, 2023

A native Midwesterner, Holly Gregory was born and raised in a small town. “A little bitty town in Illinois that is still exactly the same,” she said.
Her father, who grew up on a farm, was a corrections officer, and her mother, a teacher. “In fact, she was my fifth-grade teacher. That’s how small my town was,” the Bay News 9 evening anchor said. “Everybody knows everybody, and you’re probably related to about a third of them.”
As a child, Gregory didn’t show an early interest in journalism. Instead, she participated in Future Farmers of America. “I didn’t grow up thinking I was going to be a reporter,” she said.
Through the FFA, she became interested in farm reporting and “it evolved from there,” she said. “I’m a communicator and I was like, ‘I can do this. I like being on air.’ At the time, it was very much agriculture based.”
She studied radio and television at Butler University in Indianapolis before moving to New York City for her last two years of college. There, she attended Marymount Manhattan College. “I’d been in the Midwest my whole life and I had no idea what I was in store for,” she added.
Her professors all worked in the field with “great connections” and through one of them, Gregory was able to land an internship with journalist and television host Geraldo Rivera. His office was across the street from the CBS building, where he also filmed. “It was eye opening and interesting and crazy,” she said.
She spent so much time in the CBS building that whenever she had a free moment, she’d walk down to the CBS local news studios and introduce herself to the staff there. “I made some friends – you’d never be able to do that today,” she said. “I found some people to take me under their wing.”
Through these friendships at CBS, staff members helped her put together a professional-looking newscast reel in the studio. “I had this beginner TV tape that was the slickest thing you’ve ever seen in the No. 1 market,” Gregory said. “I’d sit at the desk doing what looks like what is a real report.”
She also worked part time at the New York Post as what was referred to one of “the copy kids.” This was before computers and email were prevalent in the office. “I would run hard copy around to the editors,” she said.
With her experience with the Post and Rivera and her slick demo tape, she applied to entry-level broadcast jobs all over the country, ultimately accepting her first full-time position at WGEM in Quincy, Illinois.
“New York was where I really got the news bug,” she said. “It made me realize this is what I want to do and also that I can’t start on camera in the No. 1 market.”
Gregory spent four years at WGEM before moving on to WHO TV, an NBC affiliate in Des Moines. “That was like reporter bootcamp,” she said. “Our news director, he didn’t pull any punches; you better get it right.”
There, she had the opportunity to cover the Iowa caucus, which is how she “got the bug” for covering politics.
Not a fan of divisive arguing, she quickly established a philosophy that was “a little different from other political reporters,” she said. “I’ve always been a general assignment reporter. I’ve always been more rounded and then I do politics. I’m more like your average person who does politics. My philosophy is to let them talk.”
Then, her husband’s company transferred him to Chicago for “a job he couldn’t turn down,” she said.
This was an opportunity for her to take the next step in her career, as well, but left her with some insecurities. “Am I able to make the job from Des Moines to the No. 3 market in the country?” she said.
For seven months, she knocked “on every door in” Chicago, Gregory said. “I’d talk to anyone who would give me the time of day to get my foot in the door.”
Then, on Christmas Eve, she received a call from a news director at CLTV – what she calls “the Bay News 9 of Chicago at the time.” The station had three staff members call out sick. “They told me, ‘We need somebody,’ and I said, ‘I’m your girl,’” she said.
She spent six years with the station, which eventually sistered with WGN-TV in that market.
“There’s no place like Chicago for covering news. It’s a trip,” Gregory said. “Until I came to Florida. That’s a whole different trip.”
In 2009, her husband was transferred to Tampa. During the family’s first three years in the area, she focused on raising their three young children.
But she missed journalism and knew she wanted to get back into it the field, taking a job as anchor/reporter with Bay News 9. “The rest has just been history here,” she said. “It was a fantastic move here, career wise.”
Since moving to Florida, she’s covered a range of stories that grabbed national attention – from the infamous Casey Anthony. Julie Schenecker and George Zimmerman trials to the Seminole Heights serial killer to the Republican National Convention to Hurricane Michael’s devastating hit to the Panhandle.
“You name any big story over the decade, and we’ve done it,” she said. “With Bay News 9, we go. If there’s a big story in the state, we’re going.”
Hurricane Michael is probably one of the more memorable stories she covered. “I was there for the duration – before, during and after,” Gregory added. “I’ve never done work like that since, as far as hurricane coverage. Calling it ‘unbelievable’ doesn’t do it justice. You just have to be there to see what it’s like. These were real stories and we got to talk to real people.”
She also covered Hurricane Ian’s recent battering of the Fort Myers area. “But after the fact,” she said. “It’s about getting these stories on TV and making people understand what happened.”
Over the past decade, as she’s covered the news, she’s seen firsthand how much the region has grown – “the population and the changing of how Tampa looks and home values,” she said. “When I first came here, everything had a foreclosure sign in front of it, it seemed like. The economics…have changed drastically since I first got here. Now it’s a bigger, more bustling, more developed city.”
Even with all these changes, she still loves her work and can’t imagine being a journalist anywhere else. “There’s still that openness, that certain something you can’t quite put your finger on about covering Florida news,” she said. “Everybody seems to be coming from everywhere else. It’s a melting pot within a melting pot and everyone has a story.”

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