Postscript Jack Pepper

World War II veteran Jack Pepper, shown here sitting on a scooter, died Feb. 4 at age 97. He also loved motorcycles and rode one until he was 95.

World War II was in its final months when Jack Pepper joined the U.S. Army Air Corps.

After completing aviation cadet training and navigator training on B-29 bombers in Gulfport, Mississippi, he was commissioned as a second lieutenant and boarded a troop ship for a 30-day tour in Okinawa.

Next stop: the Philippines.

“Out of the frying pan and into the fire,” said Jim Wilson at Pepper’s celebration of life on March 13, which would’ve been Pepper’s 98th birthday.

John “Jack” Kendall Pepper, died Feb. 4.

“Jack was heading into a dangerous situation in the Philippines,” Wilson, a longtime friend, said. “At that time, not all of the Japanese soldiers knew Japan had surrendered, and they were hiding in caves all over the islands.

“Jack was a member of the ‘Greatest Generation,’ and when he returned to the states to ‘muster out’ of the military, he was surprised to learn that he had been promoted to first lieutenant a year prior — nobody had told him.”

Friends who had gathered for Pepper’s celebration of life at Walden Woods, where Pepper had lived until he moved to Sunflower Springs Assisted Living Facility two years ago, talked of a man who loved life, loved his community and helping others — and loved motorcycles.

“He was quite the daredevil,” said Irene Ladd, his across-the-street neighbor in the 55-plus retirement community north of Homosassa.

“In 2017 when we all had to evacuate for a hurricane, Jack was supposed to come with me to a friend’s house in Dunnellon. I went to the doctor’s and when I came home, Jack was gone — he had evacuated with other Walden Woods residents to a school, so I knew he had people taking care of him,” she said.

“On Friday morning I came home and he’s polishing a motorcycle — at 95 years old,” she said. “He said he traded his car for it. I asked him, ‘What are you going to do this winter when it’s cold and raining with just a motorcycle?’ So, he decided he’d better go back to Harley-Davidson to get his car back, and they gave it back to him with no problem.”

Pepper’s son, John, said his dad once took a two-week motorcycle trip to the Smoky Mountains — by himself when he was in his 80s.

He also jumped out of a plane twice when he was in his late 70s/early 80s.

Born and raised in Miami, after he returned from his military service Jack spent his career in the insurance business.

He had divorced his first wife and married Marie, the love of his life, who died in 2014. They were married for 34 years.

“One of the memories I have of my dad is the way he cared for Marie,” John said. “She had a special diet and he went to the store every day and then came home and cooked for her ... he kept busy and didn’t quit.”

During his years at Walden Woods, Jack Pepper was a one-man welcoming committee, seeking out every new resident and giving them a rundown of things to do in the area and who to call if they needed a plumber, etc.

“The first time we saw Jack — we didn’t know it was him — he was on U.S. 19 planting flowers with a motorcycle nearby,” said Carole Clarke.

Jack had written them a letter saying, “We’ve lived here 10 years and we know who, what, where and when,” and “to get in the groove here, you should attend our 9 a.m. Monday social at the clubhouse. We have coffee and doughnuts and we tell who died, who’s sick and about the many things that go on here.”

He added, “We’re all real neighborly here. P.S. Tonight there’s a potluck supper at 5 p.m. Bring a dish ... or just come.”

Ed Greene remembered sitting with Jack and listening to him tell stories about the missions he flew in the B-29 bombers.

“He was a kind and generous man,” Greene said.

Jack Pepper loved to do woodworking and made furniture and crafts.

He was also a regular in the Walden Woods "Legends" show, dressing up in silly costumes and performing skits.

He may or may not have dressed up in just a diaper for a New Year's party.

Jim Wilson told of the time he was preparing for another person’s celebration of life and had remarked the day before that he wasn’t able to find a white cross that he would’ve liked for the service.

“The next morning there was a white cross (in the clubhouse) — without saying a thing, Jack just made that cross,” Wilson said.

Another neighbor, Barb Christy, told about the time three years ago when her granddaughter needed to interview someone who served during World War II.

“She sent me 20 questions to ask him, and as he and I had a conversation, he relived his time in the service, and shed a few tears,” Christy said. “But he was so happy to do this for my granddaughter. He was very proud of his military service.”

In 2015, Jack Pepper was an honored guest on an Honor Flight to Washington D.C., a one-day whirlwind visit to the war and military memorials.

Kathy Boggess went as his companion.

“He was so easy to talk to, and we had a great time,” she said. “When we returned to the airport and there were lines of people greeting the (veterans), he shook the hand of every child, and to every little girl he’d say, ‘Oh, darlin’ you just look lovely’ and thanked everyone for being there.

“I called him two days later to see how he was doing,” she said. “He had been outside replacing all his sprinkler heads — I thought, ‘I’ll never keep up with him!’”

A few years ago, Jack had a pain in his stomach and drove himself to the hospital. The next morning, he had surgery for a perforated bowel.

When Irene Ladd went to see him in ICU, a nurse asked her if Jack still drove.

“He drove himself to the hospital,” she told him.

Ladd said the nurse, knowing the pain he must’ve been in, was shocked and told her, “I want to be just like him when I grow up.”

Contact Chronicle reporter Nancy Kennedy at 352-564-2927 or