Silhouette of Holly Gregory | La Gaceta Newspaper

From Silhouette by Tiffany Razzano
Originally published on January 20, 2023

Holly Gregory is a Midwestern native who was born and raised in a small town. “A small town in Illinois that still retains its original feel,” she says.
Her father, who grew up on a farm, is a corrections officer and her mother is a teacher. “In fact, she was my fifth-grade teacher. My town is just that small,” the Bay News 9 evening anchor said. “Everyone knows everyone, and you’re probably related to a third of them.”
As a child, Gregory showed no interest in a career in journalism. Instead, she participated in the Future Farmers of America. “I didn’t grow up thinking about being a journalist,” she said.
Through FFA, she became interested in agriculture reporting, and “I’ve been doing it ever since,” she said. “I’m a communicator, and I was like, ‘I could do this. I love being on TV.’ At the time, my work was mostly agriculture-focused.”
She studied radio and television at Butler University in Indianapolis before moving to New York City for her final two years of college. There, she attended Marymount College in Manhattan. “Having lived in the Midwest my whole life, I had no idea what I was getting into,” she adds.
Her professors all worked in the field and were “well-connected.” Through one of them, Gregory was able to get an internship with journalist and TV host Gerardo Rivera. Rivera’s office was across the street from the CBS building, where he also filmed. “It was eye-opening, fun, and crazy,” she said.
She spent so much time in the CBS building that she would walk to the CBS local news studios whenever she had a free moment and introduce herself to the staff there. “I made some friends — you would never do that today,” she said. “I found some people to look out for me.”
Through these friendships with CBS, the staff helped her create professional-looking newscast clips in the studio. “I had this primary TV tape that was the most polished thing you’d ever seen in the top market,” Gregory said. “I sat at my desk and did what looked like real reporting.”
She also worked part-time at the New York Post as a “copy girl.” Back then, there were no computers or email in offices. “I would send copies to editors,” she said.
With her experience working for The Washington Post and Rivera, and her impressive audition tape, she applied for entry-level radio jobs across the country, ultimately accepting her first full-time position at WGEM in Quincy, Illinois.
“New York is where I got really fascinated with journalism,” she said. “That made me realize this is what I wanted to do, and that I couldn’t start shooting in the No. 1 market.”
Gregory worked at WGEM for four years before moving to WHO TV, the NBC affiliate in Des Moines. “It was like boot camp for journalists,” she said. “Our news director was relentless; you better get it done.”
There, she had the opportunity to cover the Iowa caucuses, which was the beginning of her interest in covering politics.
She disliked divisive debate and quickly developed a philosophy that was “slightly different from other political reporters,” she said. “I’ve always been a general coverage reporter. I’ve always been more general, and then I covered politics. I’m more like a regular politician. My philosophy is to let them talk.”
Then her husband’s company transferred him to Chicago because “it was a job he couldn’t turn down,” she said.
It was also a chance for her to take the next step in her career, but it also made her feel a little insecure. “Can I go from Des Moines to the third-largest market in the country?” she said.
For seven months, Gregory said, she “knocked on every door in Chicago.” “I would talk to anyone who would give me the time of day and give me a chance to get into this industry.”
Then, just before Christmas, she got a call from the news director of CLTV — which she called “the Bay Area News 9 of Chicago at the time.” Three staff members at the station called in sick. “They told me, ‘We need help,’ and I said, ‘I’m your guy,’ ” she said.
She worked for the station for six years, and the station eventually became a sister station with WGN-TV in that market.
“There’s no better place to cover the news than Chicago. It’s a journey,” Gregory said. “Until I came to Florida. It was a completely different journey.”
In 2009, her husband was transferred to Tampa, and for the first three years after their move, she focused on raising their three young children.
But she missed journalism and knew she wanted to get back into it, so she took a job as an anchor/reporter at Bay News 9. “The rest is just history,” she said. “Career-wise, it was a great move to be here.”
Since moving to Florida, she has covered a range of stories that have garnered national attention – from the infamous trials of Casey Anthony, Julie Schenek and George Zimmerman, to the Seminole Heights serial killer case, the Republican National Convention, to Hurricane Michael’s devastating impact on the Panhandle.
“For 10 years, you name any breaking news, we covered it,” she said. “With Bay News 9, we covered it. Any breaking news in the state, we covered it.”
Hurricane Michael is probably one of the most memorable stories she’s ever covered. “I was there for the entire time — before, during and after the hurricane,” Gregory added. “I haven’t done a job like it since, as far as hurricane coverage. To call it ‘incredible’ doesn’t do it justice. You have to be there to see what it’s like. These are real stories, and we get to talk to real people.”
She also covered Hurricane Ian’s recent impact on the Fort Myers area. “But that was after the fact,” she said. “The goal is to get these stories out on TV so people understand what’s going on.”
While covering the news over the past decade, she’s seen the area grow firsthand — “the demographics, the look of Tampa, the housing prices,” she said. “When I first came here, it seemed like everything had a foreclosure sign in front of it. The economics have changed dramatically since I first got here. Now, it’s a much bigger, busier, more developed city.”
Even with all the changes, she still loves her job and can’t imagine being a reporter anywhere else. “There’s still an open-mindedness here, something you can’t quite grasp when reporting in Florida,” she said. “It seems like everyone is from somewhere else. It’s a melting pot within a melting pot, and everyone has a story.”