ST. PETERSBURG — He flew combat missions during the Normandy Invasion and visited Adolf Hitler’s mountain hideout after the war.
He has counted Charles Lindbergh and six U.S. presidents as friends, led the Florida Republican Party and served in the Florida Senate for a dozen years.
On Jan. 16, Henry Benton Sayler Jr. celebrated his 100th birthday, an age that impressed even the St. Petersburg resident who has lived an impressive life.
“I never imagined I’d see 100 years,” Sayler said. “That thought never crossed my mind.”
But Sayler was quick to add that luck plays a role in the length of a person’s life.
“I could have been killed on D-Day,” he said.
So, judge a person by how they live their years, Sayler said, and not the number of years they live.
On his birthday, his family held a celebration they said was fitting of Sayler’s stature.
The first of two parades was held outside his home. Neighbors drove by and honked or walked by and screamed “Happy Birthday” as Sayler waved from his porch.
The second parade welcomed Sayler outside the St. Petersburg Museum of Fine Arts. Over 100 people — a mix of friends, family and community members — lined the road near the museum at 255 Beach Drive NE to partake in the celebration that included three firetrucks, nine military vehicles and a military flyover.
“It was humbling,” Sayler said. “It floored me, but I appreciated that so many people cared.”
Sayler was born in Georgia but doesn’t recall his time there.
“My dad was in the Army, so we moved a lot,” he said.
He believes the family was living in Kansas when they purchased their first car. He was still a toddler.
“It had a rumble seat — one of those seats that was upside down in the trunk that you had to flip over,” he said. “They’d never make anything like that today.”
He was around 7 and living in New Jersey when his parents purchased their first radio.
“We listened to Eddie Cantor,” Sayler said. “He was a comedian.”
And he was 10 and still in New Jersey when the family had their first phone installed.
“It was a wind-up phone,” he said.
It was also a “party line,” a phone circuit shared by multiple neighbors.
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“We had a neighbor who would try to listen to all the calls,” Sayler laughed. “We could hear the rustling when she was listening.”
Asked how they communicated before phones, Sayler again laughed, “I have no idea. It does sound strange.”
Even stranger, he said, was what Washington, D.C., was like in 1938 when his family moved there.
“You’d never believe it, but there was no traffic,” he said. “Not many people lived there. It was an empty place back then.”
Soon after that move, Sayler enlisted in what was then known as the U.S. Army Air Forces, which was a component of the Army.
During World War II, his father, Henry Benton Sayler Sr., was chief ordnance officer for the European Theater — including the D-Day invasion — and a “dear, dear friend of” Gen. Dwight Eisenhower, daughter-in-law Kathi Kretzer-Sayler said.
Sayler served as a P-38 fighter pilot who flew nearly 70 World War II combat missions, often escorting bombers. He was among those charged on D-Day with ensuring that German planes did not make it to the fight.
After the war, Sayler spent a month in Germany assigned to Eisenhower’s intelligence unit. It was during that time that he visited Hitler’s mountain home in Berchtesgaden. He walked through a train loaded with artwork that had been stolen by the Nazis.
“Carried away with the view” from the mountain, Sayler said, he and a British officer grabbed a few of Hitler’s china plates from the dining room and tossed them into the valley below.
Sayler stayed with the military for another 12 years, rising to the rank of lieutenant colonel.
When Lindbergh was hired as a consultant assisting the Air Force in becoming its own branch of the military, President Harry Truman named Sayler as the aviation pioneer’s liaison at the Pentagon.
“He visited every Air Force base in the world over one year,” Sayler said. “When he was done, he said the most important need was housing. We had no place for enlisted personnel to live.”
Sayler met his wife, Wyline Sayler, while stationed at Fort Benning in Georgia. He piloted the base’s private plane to Columbus to visit his sister. It was during their dinner that he spotted his future wife on a date with one of his friends.
“They didn’t date long after that,” he said.
Sayler and Wyline were married in 1947 and were together until she died in 2020.
The couple relocated to St. Petersburg in the 1950s on the recommendation of his brother-in-law Alvah Chapman Jr., the future chairman of the Knight Ridder media company who, at the time, was executive vice president of the St. Petersburg Times.
“I didn’t know anything about the civilian life,” Sayler said. “Alvah said he would teach me.”
Sayler worked in the insurance industry, then helped found and then sell local banks, like the Bank of Seminole.
But he made his name in politics as a state senator from 1966 to 1978.
Lee Sayler, one of his four sons, said his father was probably best known for “putting the state pension system on sound footing.”
But Sayler said he was also part of history as one of the senators who had to win two elections in a few-month period.
He won by nearly 8,000 votes, according to Tampa Bay Times archives, in his November 1966 bid to represent District 29. Soon after, Florida reapportioned its districts, placing Sayler in District 21. He ran and won again in March 1967, this time by 16,000 votes, according to Times archives. Among his endorsements was his former general and longtime friend President Eisenhower.
“His elections were never close because everybody loved him,” son Alan Sayler said. “That’s why he was asked to chair the Florida Republican Party when he retired from the senate.”
That position led to relationships with Richard Nixon, Gerald Ford, Ronald Reagan and George H.W. Bush.
His sons said Sayler grew close to Bush due to their shared war experiences, but was friendliest with Reagan, whom their father twice helped win Florida.
“They would talk family and wives while on the campaign trail,” Alan Sayler said. “It was not all work.”
Sayler remains a prominent local figure. On Friday, he received a COVID-19 vaccination. It was nationally televised on Fox & Friends.
His family deferred to Sayler when asked how he would like to be remembered.
“Will people remember me?” Sayler said. “I don’t know. Maybe if I live another 100 years? I’m going downhill now, although I’m not sure how fast. I’ll just keeping enjoying what I have left.”
Correction: Henry Benton Sayler Jr. was a lieutenant colonel in the United States Air Force. An earlier version of this story misidentified his rank.