CHATHAM — Thomas R. “Tim” Pennypacker, II, is being remembered as a caring neighbor, as the officiant at countless marriages, as a lover of local history, and as a plain-talking politician with a strong sense of duty toward his community.
Mr. Pennypacker died Sunday at the age of 73, shortly after having been diagnosed with cancer.
“Our thoughts and prayers go out to his family,” Board of Selectmen Chairman Dean Nicastro said Monday, before observing a moment of silence. A celebration of Mr. Pennypacker’s life will be held this fall.
Though his family roots in Chatham date to 1895, Mr. Pennypacker was born in Newport, R.I., where his father was serving in the U.S. Navy at the end of World War II. He spent his childhood in Chatham and Dover, Mass., before attending military school. He attended college in Texas for a year, but soon felt the pull of the sea and moved to Chatham. Finding he couldn’t make enough money as a commercial fisherman, Mr. Pennypacker took a job with the Woods Hole Oceanographic Institution, and cruised the world on research trips.
It was on one of those trips when he received a letter from Chatham Police Chief David Nickerson who offered him a seasonal patrolman’s job. He returned to town and ran the harbor patrol for a summer, and when a full-time position eventually opened up, Mr. Pennypacker joined the force. He was a patrolman for 10 years, but sometimes clashed with his superiors over a fundamental difference of opinion, as he told The Chronicle in a 1988 interview.
“I didn’t think you had to give a ticket to everybody. I viewed the job, rightly or wrongly, as just what it is: protection of life and property and serving the public,” he said. In 1975, while still on the force, he decided to run for selectman. The following day, the chief asked him for his resignation, saying he couldn’t be both a full-time police officer and a full-time selectman.
When he was elected at the age of 30, Mr. Pennypacker was one of the youngest men to hold that office in Chatham, and learned the ropes from fellow board member Ed Harrington. He held office until 1979, when he took a two-year hiatus for family reasons, and then won election again by a wide margin. This time, he served with an even younger man, William Litchfield, who was just 25 when he was elected. They became fast friends.
The three selectmen then were in a very small office “and were together from nine o’clock in the morning until five o’clock in the afternoon,” Litchfield said. He and Mr. Pennypacker would often socialize after work as well. Former Selectman Eileen Our said the two young men were a vital force on the sometimes-stodgy board, and Mr. Pennypacker had his hand on the pulse of the town.
“Everyone loved him because he was vivacious and outgoing, and he loved this town,” she said.
As a selectman and town assessor, Mr. Pennypacker had a reputation for speaking his mind, sometimes with brutal honesty.
“Tim was a dynamic personality,” Litchfield said. He cared deeply about Chatham, its people and its history, and didn’t hesitate to stand up for those values. Mr. Pennypacker remained a selectman until 1988, when the town’s new charter increased the board to five part-time members.
By that time, he had already begun a vocation that would leave a powerful legacy around the Cape: serving as a justice of the peace. It is not possible to know how many couples Mr. Pennypacker united in marriage, but it wasn’t hard to know why he was so sought-after, Chatham Town Clerk Julie Smith said.
“Everybody knew him, and he knew everybody,” she said. “He was just a great guy.” It is likely that, in Chatham and all around the Cape, he officiated at hundreds of weddings – including one in a tree and another in a hot-air balloon. He always left the bride and groom feeling as if they were among his closest personal friends.
“He met with us just once before the wedding, but during the ceremony at Harding's Beach he was able to perfectly summarize the feelings of both myself and my wife,” said Chronicle editor Tim Wood. “I'd known Tim for years but he'd only met my wife once.”
Mr. Pennypacker was well known for his vast knowledge of local history, and also for his keen wit.
“Tim was a mimic,” Litchfield recalled. “He had nicknames or descriptions for a wide number of people, many of whom were not aware of those nicknames, and ought not ever to become aware,” he said with a chuckle.
But behind that sense of humor was a sense of optimism, Our said.
“The glass was always full, even when it was empty,” she said.
His service to the community included 30 years as a deputy Barnstable County Sheriff, 50 years as a member of the local Masonic lodge, and many years on Chatham’s cemetery commission. He also served as the town’s delegate to the Barnstable County Assembly.
“He would want to be remembered as somebody who cared deeply about the community,” Litchfield said. For years, when Mr. Pennypacker was a police officer, he would keep an eye open for local people who were experiencing hard times, and with help from a close friend who was a philanthropist, would deliver groceries or other essentials. “And he’d do it quietly,” Litchfield said.
“He used to say about people, ‘They’re the finest kind,’” Our recalled. “That’s an old Cape Cod expression. And he was the finest kind, too.”