Jesse Oscar Bryan was born near Rose Hill, AL, the son of Andrew Jackson Bryan. According to an affadavit in the Pension Application file for William B. Boyett, Oscar's grandfather, Andrew and his family moved from AL to Walton County, FL, near Portland in November, 1895 when Oscar was 12 years old. He and sons Lee and Oscar then went back to Covington County in December, 1895 and moved William B. Boyett to Portland in south Walton County.

When his family moved to Portland, Oscar and Lee and their father, Andrew, worked at the sawmill in Portland, according to the story told by Will Bryan to his son, Willie.

Jesse Oscar Bryan was a farmer. His children called him "Poppa". To his friends, he was "Oscar". He rented land from Rob Jones of the Children's Home community before buying 40 acres of land from Owen F. Lee on 14 June 1923 on the west side of Pond Creek in Okaloosa County. The land was described as NW 1/4 of NW 1/4, S36, T5N of Range 22W. [His father Andrew bought 40 acres one the east side of Pond Creek the same year from Owen F. Lee.] He and son Marvin Bryan cleared this land, taking in about 20 acres the first year. They built a log house there which was still in use in the late 1940's. At that time, only a "pig-trail" road existed in front of the house. It had three trails-two for the wagon wheels and one for the mule to walk in. The main road was about a half mile to the west going by the Rock Hill Church and school house and on up Horsehead Creek to Steele's grist mill. The rural mail carrier (Carl Hurston from Laurel Hill) did not deliver to the house then. The mail box was at the crossroads north of Bethel Church, about 1.5 miles from the house. After the land was cleared, Oscar worked in the turpentine industry and his son Marvin worked the crops. Cotton was planted during the third year. This was the "cash" crop. Laurel Hill had two cotton gins at that time and the "Dixie Flyer" train made two trips a day. There were 18 business houses including dry goods, hardware, drug and grocery stores, several boarding houses and a hotel, a telephone exchange and two banks. A paved road connected Laurel Hill to Crestview in 1930. According to Bradie Bryan, they moved to the property in 1919 and started the clearing process and began farming. She was only 5 and Marvin was 9. Apparently the final payment was made and the deed transferred in 1923.

During the first years, Oscar worked part of the time at a sawmill operated by Frank Harrison which was located in the bottom just south of David Miller's place. He used the money to buy essentials that couldn't be raised on the land like flour, coffee, rice, snuff and tobacco. Meanwhile, Marvin and his mother did much of the actual farm work

Daughter Bradie remembers that neighbors would come to visit late in the afternoon or early evening and they would sit around and talk or tell stories. She would sometimes play the organ for singing songs. Some of the neighbors were Mr. German Bass and David Miller. At other times, Sadie would read from the family Bible. She said that some of the Bryans were also into Irish-type dancing. She said that Oscar would dance and would also do square-dance calling. She had heard him do that.

The original 40 acre tract (NW quarter of NW quarter, section 36, township 5, Range 22 west) was sold on November 23, 1931 to Barzilla H. Beard and wife Eunice Beard for $500. (Okaloosa County Land Records, Book 24, page 176). This tract of land was about 3/4 miles due west of the property of his father, Andrew Jackson Bryan, who owned 40 acres on the east side of Pond Creek in the NE quarter of NE quarter of section 36. It is about 7 miles south of the Alabama line. Part of the reason for the sale was to pay off a debt to merchant Tom Spears incurred for fertilizer, seed and other supplies. So, the property was sold and Oscar and family moved to the "Dan Moore place" where John Hallford and his oldest daughter Hettie lived. Bradie and Roy Beasley were married in January 1932 and they lived at the "Charlie Moore place" nearby.

He was generally good-natured and jovial, often joking and laughing, but also had a quick temper and was known to "fly off the handle" on occasion. He was a strong-willed person and there was no question about who "the boss" was in his family. He tended to be impatient and had what some would call "an itching heel". He was not one for long visits and often would be ready to go back home or elsewhere shortly after arriving for a visit with the family. He was about six feet tall and slender until his retirement years when he gained a little weight. He was a man of great appetite and was especially fond of pies, occasionally eating a whole pie at one sitting. He loved to go deer hunting and sometimes went with his brother Will and his sons who lived in the DeFuniak Springs area. He dipped snuff. He loved his grandchildren (and great-grandchildren) and one of the rituals when they visited him was to go for a "horsie ride" by sitting on his foot. He would cross his legs and bounce the youngster up and down on his foot. Sometimes he would sing or chant this little ditty during the ride which for some reason has stuck in my mind: "Roberty Boberty, big-bellied Ben. He could eat more meat that five or six men. Eat a cow, eat a calf; eat a whole, eat a half. Roberty, Boberty, big-bellied Ben."

When he died, the pallbearers were his grandsons. Robert Hallford, Royce Hallford, Bob, and Gene Bryan, Roy Beasley, Jr. It was a bleak, rainy day when he was buried at Pleasant Ridge cemetery along with many of his relatives.

Jesse O Bryan