Thomas O’Sullivan moved to St. Augustine to escape the bitter cold of Boston. Since arriving, he has warmed many hearts through his good-humored nature and his willingness to lend a hand.
Like most transplant residents, he was drawn to the area’s unique history, in addition to Florida’s alluring fishing and golf culture. His move was a dramatic, albeit welcome change from the hometown where he owned a series of barbershops.
Eventually growing bored with the typical retirement hobbies, Thomas found a way, using the barbering skills he accumulated over the past 38 years, to raise the spirits of St. Augustine’s homeless population. For the last two years – every Wednesday – Thomas has cut hair and trimmed beards at the St. Francis House downtown.
“There’s always a big turnout,” said Thomas. “I stay there for about three hours in the morning, providing haircuts for at least 20 people. It makes me feel good, making other people feel good, especially people that are down and out on their luck. I figure it can happen to anybody.”
In addition to serving the community during his retirement, Thomas still maintains ownership of Sully’s Barber Shop in Boston.
“The barbering business has been good to me,” said Thomas. “I owe most of it to my mother who was a determined, hard worker. She never asked for help.”
His mother was an Irish immigrant, traveling from Cork City, Ireland to the U.S. sometime in the 1920s. Irish heritage would continue to play a role in their lives as Thomas’ father earned a living as a musician, featured on Boston radio stations as the Jack O’Sullivan Irish Band during Irish Hour each week. His earnings kept the family of 10 afloat until he made enough money to open a variety store.
Thomas was the youngest of eight children and only seven years old when his father died. His mother tried to manage the variety store as her late husband did but eventually left to work for a college, all the while raising the children on her own.
While he never found himself staying in a shelter during his childhood or later in life, those lean times helped Thomas develop a great appreciation for hard work and learn the importance of lending a helping hand.
Regardless of their situation, many of the homeless that Thomas encounters are still trying to earn a living, and sometimes a clean shave and trim gives them just the boost of confidence they need to find a job.
“I meet a lot of guys that really try. They tell me that St. Francis House is a big help to them and if they didn’t have that place, they wouldn’t know what to do,” said Thomas. “They can’t thank me enough. They have job interviews and they feel really good about getting their hair cut.”He has met several interesting people along the way and enjoyed the stories they shared. He’s met a former second baseman from the 1970’s New York Yankees and a son who couldn’t continue the gumbo business he built with his father after watching him pass away. The thing they both have in common is need and people like Thomas are there to help.
Photography by Rob Futrell.









