From the opening of a long-gone waterfront restaurant to the rise of the Seaport skyline, from the heartbreak of 9/11 and the Boston Marathon bombing to the resilience of a community during a global pandemic … Rick Winterson has been there to document it all.

This month, Rick celebrates 25 years as a reporter and Senior Editor for South Boston Online — a milestone that represents thousands of stories, millions of words, and a quarter-century of faithfully chronicling the life of this neighborhood.

“All in all, I’ve written thousands of articles,” Rick reflects. “But my personal favorites always involved the local people, interviews, and happenings in South Boston.”

The First Byline

Rick joined South Boston Online in 2001 as a proofreader. Within a week, he was asked to write a story about the opening of “Jimbo’s,” an addition to Jimmy’s Harborside. He gladly accepted.

That February 2001 article — 500 words and three photos — became the first of what would eventually total thousands. Later that same year, Rick covered the passing of Congressman Joe Moakley and wrote about the devastating events of September 11 and the impact on South Boston. It was a baptism by fire into community journalism.

He never looked back.

Chronicling a Changing Skyline

Over the past 25 years, Rick has carefully followed one of the most dramatic transformations in Boston history — the development of the South Boston Seaport.

He covered:

The opening of the Institute of Contemporary Art

The debut of the Boston Convention & Exhibition Center

Fallon’s VERTEX project

The massive WS Development complex, now nearing completion.

Rick attended groundbreakings. He stood at ribbon-cuttings. He watched cracked asphalt and parking lots evolve into a bustling waterfront district.

“The Seaport is wonderful,” he has said. “It was badly needed.”

Reporting Through Crisis

Rick’s work has also documented some of the most difficult moments in recent history.

He covered the 2013 Boston Marathon bombing and its profound effect on South Boston, including the creation of Martin’s Park, named in honor of Martin Richard.

He conducted an exclusive phone interview with Congressman Stephen Lynch, who called Rick from N’Djamena, Chad, to discuss his trip into Darfur during a devastating famine.

And during the COVID-19 pandemic, Rick wrote steadily — before, during, and after — capturing the fear, uncertainty, resilience, and recovery of the neighborhood he loves.

The Stories That Matter Most

While Rick has written about major developments and historic events, his personal favorites have always centered on local people.

He has profiled teachers, veterans, clergy members, scholarship winners, first responders, community activists, and lifelong South Boston residents. Among his most cherished subjects was Sister Evelyn Hurley, the beloved longtime educator at Nazareth (now South Boston Catholic Academy). Rick wrote many articles about Sister Evelyn, following her remarkable life and continued connection to the community well into her 100s.

A Recognized Community Voice

A graduate of MIT with a degree in chemical engineering, Rick served in the military working on nuclear weapons testing before spending 40 years in private industry across the United States and abroad. His professional work demanded clarity, precision, and technical writing — skills that later shaped his journalism.

Over the years, Rick has earned well-deserved recognition, including:

The Henry Knox “Unsung Hero” Award from the South Boston Citizens’ Association and A Community Service Award from Boston Police Department Station C-6

Rick will turn 90 in June. He remains spry, sharp, and endlessly curious. He continues to attend events, conduct interviews, and submit articles with the same enthusiasm he brought to that first story in 2001.

For 25 years, he has captured the voices, milestones, celebrations, struggles, and spirit of this community. And for that, we are grateful!