SOUTH BOSTON ONLINE
THURSDAY FEBRUARY 19, 2026
VOLUME XIX- ISSUE 74
Rick Winterson Marks 25 Years of Telling South Boston’s Stories
F
rom 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,” R ick ref lects. “But my personal favorites always involved the local people, interviews, and happenings in South Boston.”
write a story about the opening of “Jimbo’s,” an addition to Jimmy’s Harborside. He gladly accepted. That Fe br u a r y 2 0 01 a r ticle — 500 words a nd three photos — became the first of what would eventually tota l thousands. Later that same year, R ick 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 communit y journa lism. He never looked back.
The First Byline
Chronicling a Changing Skyline
R ick joined South Boston Online in 2001 as a proofreader. Within a week, he was asked to
Over the past 25 years, R ick has carefully followed
one of the most dramatic tra nsformations in Boston histor y — 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 r ibb on- c ut t i n g s. He watched cracked asphalt and parking lots evolve into a bustling waterfront district. “The Seaport is wonderful,” he has said. “It was badly needed.” Continued on Page 2