The son of a Winthrop firefighter and father of current Chief Paul Flanagan and Captain Charles Flanagan, Chief Flanagan grew up in the shadow of the Beach firehouse.
When he married Marilyn (Floyd) in 1948, they made their home there, and the chief was proud to say that he never lived anywhere else or wanted to.
Chief Flanagan served on the Winthrop Fire Department for 44 years until his retirement in 1990. He continued a tradition of Flanagans on the Winthrop Fire Department that began with his father’s appointment in 1904 and continues to this day with his sons Paul and Chuck.
His four-decade career was marked by some of the most spectacular disasters in the town’s history, from an airliner crash to devastating storms, a prison riot and dozens of major fires and lifesaving rescues.
At about 5:40 p.m. on October 4, 1960, an Eastern Airlines Lockheed L-188 turboprop Electra crashed on takeoff when the plane flew into a large flock of starlings. The plane rolled and crashed into Winthrop Harbor, where it broke apart and sank off the Cottage Park Yacht Club.
Chief Flanagan led the fire department’s response, marshalling not only the firefighters but also the many residents who waded into the harbor to help retrieve the dead, many of whom were strapped in their seats and drifting toward shore. Only 10 of the 72 passengers and crew aboard survived.
Chief Flanagan also was the ranking officer during a major prison riot at the Deer Island Prison in October, 1961. He described a frightening scene involving inmates setting their mattresses afire, but being unable to escape their cells.
There were many major fires over his years in service to the town, including one on Point Shirley that involved four houses on Shirley Street. Of that fire, he wrote: “Four houses were fully involved, and a fifth had started to burn. The temperature was three degrees above zero, snow was falling and the wind was from the northeast at 45 mph.” The firefighters were able to stop the progression of the fire, which threatened all of Point Shirley. In the course of the effort, Chief Flanagan suffered a serious eye injury from windblown debris, but he stayed on scene until the fire was under control.
But Winthrop’s disasters don’t always involve fire. In 1978, shorefront homes were destroyed when a blizzard coupled with high tides resulted in arguably the worst storm in living memory.
Chief Flanagan was in charge of the department for the first 48 hours, managing the response to literally hundreds of calls for assistance and helping coordinate the National Guard response to evacuate residents in hard-hit areas along Shore Drive. At the same time, his own home off Shore Drive was flooded with 8 feet of seawater in the basement.
Chief Flanagan was involved in many rescues, pulling a burned child from the flames of a fire on Undine Avenue and suffering burns himself. The young boy survived.
He twice rescued members of the Winthrop Fire Department by carrying them out of burning buildings after they had been overcome by smoke.
Another rescue occurred on a bitterly cold January day in the early 1950s, when four boys from Revere set out in a dory off Fort Heath but neglected to bring oars. The wind blew them toward the open sea, but a bystander saw them and called the fire department. Chief Flanagan and the late Francis Riley set out in a fire department boat, but before they could reach the dory, the boys had jumped overboard and tried to swim to shore. They managed to get the boys into their boat, but to do so Chief Flanagan had to dive into the icy water to help get the biggest boy aboard.
His legacy will continue in town on Christmas Eve, with the traditional visit from Santa Claus riding on the top of a Winthrop fire engine through every neighborhood in town.
The Santa visits began modestly, with Santa wearing a borrowed suit. Townspeople were so happy with the first Christmas Eve visit that then-Captain Flanagan led an effort to raise money to buy a high quality Santa suit and three reindeer. Other firefighters built the original sleigh, and Chief Flanagan mapped out the route. He played the role of Santa for five years, turning the part over to other firefighters as the years passed. Continuing the tradition, Capt. Chuck Flanagan has been Santa Clause for the past 20 years, riding behind the same three reindeer that were purchased back in the 1950s.
Chief Flanagan leaves his wife of 64 years, Marilyn (Floyd), three sons, Chief Paul Flanagan and his wife Susan of Winthrop, Capt. Charles Flanagan and his wife Trisha of Winthrop, Robert Flanagan and his wife Linda of Summit, N.J., and four grandchildren: Andrew Flanagan of Newburyport, and Julie, Jeff and Paul Flanagan of Summit, N.J., as well as many nieces, nephews and friends.
Visiting hours will be Friday evening June 8, from 4-8 p.m. at the Maurice W. Kirby Funeral Home, 210 Winthrop Street. A funeral Mass will be said on Saturday, June 9 at 10:00 at St. John the Evangelist Church, 320 Winthrop Street, Winthrop. Interment will follow at the Winthrop Cemetery, Cross Street section.
In lieu of flowers, donations may be made to the Winthrop Fire Department Building Improvement Fund, care of Chief, Winthrop Fire Department, 40 Pauline St., Winthrop MA 02152.
Chief Flanagan inducted into the Winthrop Athletic Hall of Fame for his athletic contributions on the Winthrop High School baseball, basketball and football teams. He was a member of the Fire Chiefs Association of Massachusetts and the International Association of Fire Chiefs.