William Hennessey, longtime teacher and principal in Boston’s schools, dies at 92

Mr. Hennessey helped found the West Roxbury Friends of Rosie’s Place.
Mr. Hennessey helped found the West Roxbury Friends of Rosie’s Place.(Handout)

Because World War II was underway when William Hennessey graduated from Boston Latin School, he and the rest of his freshman class at Harvard College began classes early, in July 1943, to finish as much coursework as possible before heading to the military.

By the following February, he was still 17 when he enlisted in the Army. After first being sent to the University of Maine to study engineering, he was shipped to Camp Blanding in Florida for basic training, which included “the solemn repeated statements from sergeants and officers, ‘Look to your right; to your left. One of you will probably be dead by Christmas,’ ” Mr. Hennessey would later write.


Two weeks before finishing basic training, he was sent to language school at the University of Minnesota to study Japanese, a step toward serving in the Counter Intelligence Corps. In an essay about his service during the war, he recalled that by the time winter began in late 1944, “those ominous predictions at Blanding proved true: every edition of the Army Times, especially after the Battle of the Bulge, listed barracks mates as casualties.”

“There but for the grace of God and a good test score,” added Mr. Hennessey, who didn’t forget the lessons of sacrifice and luck he learned in wartime.

He was a longtime teacher and principal in the Boston Public Schools and as his career drew to a close, Mr. Hennessey helped his wife, Alice, and their neighbors found the West Roxbury Friends of Rosie’s Place. Mr. Hennessey was 92 when he died in his South End home July 20.

“He was a witty man,” said his son Sean, who also lives in the South End. “He was incredibly well-educated, but at the same time was incredibly humble.”

Teaching was the family profession. Mr. Hennessey’s father taught French and Spanish at South Boston High School, and his mother taught at South Boston High and at Smith College.


While attending Boston Latin, Mr. Hennessey earned money by stacking books at the Boston Public Library’s Central Library in Copley Square, and by selling tonic in Fenway Park’s stands.

To the end, he remained a city boy, never getting his driver’s license. He made do with public transportation, even when in the early 1960s he and his wife “bought a big old ark of a house in Hull for summers away from the city,” he recalled in the 20th anniversary report of his Harvard class. To teach college classes while his family spent the summer in Hull, “I’ve been lucky enough to commute by boat,” he noted.

“He loved the city of Boston with a great deal of passion,” Sean said. “I think he always kept his feet planted firmly on the ground and remembered where he came from. He was a proud son of Dorchester.”

Born in Harley Hospital in 1926, William Francis Hennessey was the oldest of five children, a son of Joseph Aloysius Hennessey and the former Angela Cecelia McManus.

Mr. Hennessey was 8 when his mother died of complications from childbirth, after his youngest sister was born. At various times he lived in four houses in Dorchester as a boy and graduated in 1943 from Boston Latin.

He served in the Army for 28 months, and while stationed in Maryland, “we did get a privileged, gruesome shocker,” he wrote in a wartime recollection for his Harvard class reports. One of his instructors had been with the first Counter Intelligence Corps unit to enter the Auschwitz and Buchenwald concentration camps. The photos the sergeant brought back were “the first stateside classified evidence of the Holocaust,” Mr. Hennessey wrote. “This was why we fought.”


Taking course overloads after the war, he graduated from Harvard College in 1947 and finished a master’s in education the following year at Boston State Teachers College.

Mr. Hennessey taught at a few schools in Boston and served as principal at the Patrick T. Campbell, Martin Luther King, Woodrow Wilson, and Patrick F. Lyndon schools before retiring in 1984.

“He prided himself in the fact that he took his students from Roxbury and Dorchester by streetcar and subway on walking tours of Colonial-era sites downtown before Boston’s Freedom Trail was established in 1951,” his son wrote, “visiting the Boston Massacre Memorial on the Common, the Old State House, Old South Meeting House, Faneuil Hall, and the Massachusetts State House.”

While teaching in his early career, Mr. Hennessey attended Suffolk University Law School at night and graduated in 1958. “The most worthwhile result of law school, to put it terribly inadequately, was that I met my wife, a perfect woman,” he wrote in 1957 for the 10th anniversary report of his Harvard class. Mr. Hennessey married Alice Moloney in 1955. They lived in the Back Bay and Jamaica Plain before settling in West Roxbury, where they stayed for more than 50 years.


Alice Hennessey, a former staff director for the Boston City Council and former longtime aide to Mayor Thomas M. Menino, died last year.

“The worst thing Reagan did was to teach us all to be more greedy and selfish,” Mr. Hennessey wrote for a class report in 1992, a few years after President Ronald Reagan’s second term ended. “In atonement, Alice and I volunteer for Rosie’s Place, a women’s shelter in Boston, and Sunset Point, a summer camp in Hull for needy children.”

Along with holding fund-raisers at their West Roxbury home for Rosie’s Place, Mr. Hennessey volunteered as a docent at the Boston Athenaeum, and served on several boards, including those for the Old South Meeting House and Light Boston.

A longtime student of the city’s history, Mr. Hennessey was proud that he saw Babe Ruth and Ted Williams play in Boston, and listened to Billie Holiday perform in the city. Mr. Hennessey also was a member of the Harvard Club for more than 70 years.

“He immersed himself in the history of the city,” Sean said, adding that “he was quite proud of tradition, and he was quite proud of his family.”

A service has been held for Mr. Hennessey, who in addition to his son Sean leaves another son, Billy of Milford; three daughters, Mara of New York City, Paula of Cambridge, and Katie of Shelburne Falls; a sister, Sister Mary Hennessey of Chicago; and two granddaughters.

Not long out of Harvard in the late 1940s, Mr. Hennessey “sought and received a commission in Army intelligence” by joining the Army Reserve, he recalled in his military service essay. He wrote that he earned his extra paycheck with summer active duty that included “mock-war exercises; map reading; aerial photo interpretation; new combat thinking.” As US military policy changed, however, he decided it was time for a change, too.


“When these Army ‘dry-runs’ began using putative small-blast atomic bombs in tactical maneuvers instead of exclusively big-time last-option strategic exercises,” he wrote, “I decided to take a pass on all the Army Reserve ‘perks.’ ”

He ended his military career, resigning as a major, though he knew his protest might have little impact beyond his own conscience. “Was that last move quixotic?” he wrote. “Still uncertain.”

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