By Ginger DeShaney
From his first story covering Jimbo’s Fish Shanty, to his four stories about Sister Evelyn Hurley, to numerous articles about the Seaport District — and everything in between — Rick Winterson is the face of South Boston Online.
Rick, who is celebrating 20 years at the newspaper this week, estimates he’s written at least 4,000 stories for South Boston Online (which he figures equates to about 2 million words).
Every story Rick has written is important because “it’s news about the old hometown,” he said. “We are a community newspaper. This is a community worth writing about.”
He signed on with South Boston Online in 2001 as a proofreader. A week later, he was asked to write a story on the just-opened Jimbo’s, a branch of Jimmy’s Harborside (both of which are long gone). “I said I was happy to do it,” Rick said. “I really love to write.”
The 500-word story and three photos were published in the Feb. 22, 2001, issue.
It was the first time he interviewed someone for an article, but it came naturally to him.
“The [Jimbo’s] manager was grateful. Jeanne [Rooney, the South Boston Online publisher] loved it. I was pleased with myself,” he said.
After that first story, Rick started writing regularly, eventually attaining the title of Senior Editor.
Rick was born and raised in the suburbs of Boston. He has a degree in chemical engineering from MIT, graduating in 1956. After his military service on nuclear weapons testing (service was mandatory back then), he worked for 40 years in private industry around the United States and the world before retiring.
In these jobs, Rick had done a lot of writing (reports as well as engineering and science documents), which required proper English, excellent grammar, and accuracy, setting the stage for his future career.
He originally came to South Boston in 1997 for the Answer House for his alcohol addiction. “I’ve been, thankfully, clean and sober for 24 years now,” he said.
As part of that recovery, he was required to get a job, so he started working at Harnett’s, an herbal store in Harvard Square, and ended up managing it. But competition from big pharmacies eventually put Harnett’s out of business.
After that, Rick performed other jobs, running costumed guided tours for Old Town Trolley, working as a professional actor (he joined StageSource here in Southie), and serving as a newswriter/broadcaster for five years with Chris Lovett at Boston Neighborhood Network (BNN).
“South Boston is a fascinating place. The people are, the history is. South Boston has a renown as an urban neighborhood. I just love the place,” said Rick, who lives in Andrew Square. “There’s a strong community spirit, a number of agencies that do good.” He also mentioned the park lands, the beaches, the nice people, and the proximity to downtown.
The vast majority of Rick’s wide-ranging stories are local to Southie.
“I’m fascinated by South Boston as a source of stories … It’s a unique neighborhood,” said Rick, who is a spry and energetic 84. “I’ve lived all over the world and South Boston is unique.”
In his first year, Rick covered U.S. Rep. Joe Moakley’s death and 9/11’s impact on South Boston.
He’s followed the 10-year development of the South Boston Seaport District, writing many articles about it, from the opening of the Convention Center to where it is today. “I attended groundbreakings and ribbon-cuttings. I followed it all the way along,” he said.
“The Seaport is wonderful.” The area originally featured cracked asphalt and cheap parking lots. “It was an unoccupied territory. [The development] was badly needed.”
It’s hard for Rick to nail down his favorite personal profiles, but if forced to choose, he would single out the four articles he wrote about Sister Evelyn Hurley, who taught for more than 40 years at Nazareth, which became St. Brigid’s School, and which is now South Boston Catholic Academy. She turns 106 in March. After she retired and moved to Kentucky, Rick wrote a story each time she came back to visit the community. This year she couldn’t come back because of the pandemic, so Rick did a phone interview with her for a story.
Covering the annual St. Patrick’s Day Parade and its accompanying events is one of Rick’s most enjoyable assignments. He also cites writing about the annual fundraisers (which have been put on hold because of COVID-19), the street festival, political figures, award winners, scholarship recipients, and life-savers.
“I really enjoyed doing all 4,000 articles,” he said. “I’ve been very fortunate. I’m in good health and doing something I truly love.”
Of all the jobs Rick has had, writing for South Boston Online is his favorite. And, at 20 years, it’s the longest he’s been in one job. “I love it because I love South Boston.”