Bob Penney grew up on Martha’s Vineyard, graduating from the Oak Bluffs High School with a class of just 10 students. “I finished in the top 10 in my class,” he likes to quip. He’s lived in a small home overlooking Oak Bluffs Harbor on East Chop Drive for several decades. And when he was in his freshman year at Tufts University, in 1941, Pearl Harbor was bombed.
And eight decades later, his friends, family, and neighbors stopped by his Oak Bluffs house on Monday, August 21, to eat cake and celebrate his 100th birthday, an accomplishment worthy of presidential recognition.
“It is a privilege to wish you a happy 100th birthday and to thank you for your inspiring service in the United States Navy,” read a letter signed by President Joe Biden.
Today, Penney is sharp and witty for his age, and likes to tell a good joke. “I’m an Islander,” he said during a recent interview. “I’ve lived here all my life … Well, not quite yet.”
His friends and family describe Penney as a good neighbor willing to lend a helping hand, even as he’s hit the milestone birthday.
Penney’s experience in World War II wasn’t what you’d expect, or at least how it’s depicted in the movies. As he tells it, he joined the Navy while in his freshman year, figuring that his college days were over. But as it turned out, the Navy had so many recruits at the time that he was able to go back to Tufts for 18 months. And when he did eventually get called back to the Navy, he said he spent the war training.
“We were winning the war, and the Navy just had too many guys,” Penney said. “They didn’t know what the hell to do with us all. They switched us from one training program to another.”
It wasn’t all smooth sailing. When he first went to training camp, he says that on the first night, one of the recruits died by suicide. He remembers thinking, “What have I got myself into?”
Penney started his flight training at Naval Air Station Pensacola in Florida. There he says he first learned to fly a Piper Cub, a light, single-engine plane. He eventually learned to fly multiengine planes, including the Navy’s equivalent of the Flying Fortress, as well as amphibious seaplanes called Catalinas.
Penney says that at the time, he especially enjoyed multiengine planes because he wanted to become a commercial pilot. It wasn’t until later that he realized that would be difficult, because so many coming home from the war were trying to do the same thing.
Penney eventually trained at naval bases in San Diego, but he never served in combat, or even left the U.S., during the war, although he says that once he was shot at by friendly fire.
While stationed in Florida, he likes to joke, no Japanese planes ever flew past him.
Penney was stationed in Florida when victory was declared in Europe. He remembers flying with other pilots a short distance, from Jacksonville to Key West, flying really close to the land and making a lot of noise. “That was our celebration,” he recalled.
He says there wasn’t much in terms of fanfare when he eventually did return to the Island after the war. As he remembers, soldiers were being discharged individually, and returning one by one. He doesn’t recall any parades or special recognition.
He was given the option to serve at a naval base in Alaska, but decided to go home instead. He was married by that time, and ready to go back to school.
“It’s a terrible thing to say, but World War II was the greatest thing that ever happened to me,” he said. He enjoyed training and learning to fly planes: “It was fun.” And, like a lot of World War II veterans, the G.I. Bill paid for his education.
On the Vineyard for a brief time, he held a number of odd jobs: a milkman, postal worker, and he worked for his father’s restaurant, which was on Main Street in Oak Bluffs at the time. “Like Linda Jean’s,” he said of the restaurant (he says that life on the Vineyard was different then. Quieter and colder, he recalled. Penney remembers Oak Bluffs Harbor freezing over).
Working at his father’s restaurant was not his favorite job; he says he didn’t like it much, and soon after returning to the Island, he was admitted to Boston University’s law school, which he was able to attend thanks to funding from the G.I. Bill.
A fellow classmate would connect him with a job at Liberty Mutual. And he settled down in the Boston area, had two kids, and 36 years later, he retired as assistant vice president and senior counsel at Mutual before moving back to Oak Bluffs.
Penney says that he wonders why he was never brought back to the service for the Korean War. He said that many fellow service members were, but he never got the call. Sometimes he didn’t understand.
While never becoming a commercial pilot, he would sometimes fly dignitaries in a program called the Weekend Warriors — a group of veteran pilots — and took his own joy rides, keeping up his flight hours. One of his last and most memorable flights, he said, was taking his two sons on a trip around the Island.
On Monday, during his special birthday party, and surrounded by grandchildren, friends, and neighbors, Penney’s son, Rob Penney, was on hand. He said that his father is someone who enjoys lending a helping hand, although he’s slowed down in his later years. After retiring from Liberty Mutual, he said, Penney would offer legal advice to neighbors and friends, and help with some cases.
“He enjoyed it,” the younger Penney said of his father’s party.
A special moment in the celebration was that letter from the president.
“We remain forever indebted to you and all those who have worn the uniform and sacrificed beyond measure for our cherished freedoms,” was written in the letter. “On behalf of a grateful Nation, I send my best wishes to you on this special day.”
