1926-2025: Curtis Massey served as the first black mayor of Oakland

The town of Oakland had fewer than 700 residents when Curtis Massey was elected the first black mayor in 1975, and he said the citizens were content with the size of the town.

“I don’t think anybody in town really wants us to get any bigger,” he said at the time. “One of the reasons people like it here is because it is peaceful and quiet.”

Massey served just one three-year term but continued to consult elected officials and town staff after he left office.

The former mayor died Jan. 29 at the age of 98.

Massey was born in Orlando July 12, 1926, to Frank and Flossie Nelson Massey, and he always told people he was the seventh of seven sons.

At a young age, he met and married Nellie Vernell Paulk and then joined the military. Massey was ordered to go to Germany to serve during World War II, but he never made it. He and three other men on the train contracted mumps and were told to exit the train at the next station to avoid infecting any other men, said his daughter, Rhonda Massey Hall Steib.

“He felt like it was forever in the hospital, but I think it was only a month in the hospital because he really did have a bad case,” she said. “He went back to (his base), so he didn’t see any action. He used to talk about training, he was a rifleman, and they used live rounds. He didn’t actually have any war time.”

After his military service, he returned to civilian life and settled in Tildenville. Shortly after returning home, he went back and finished his high school diploma by attending night school. While there, he met his agriculture teacher, Mr. Johnson, with whom he developed and maintained a friendship. For many years, he assisted Johnson by providing citrus for Charles R. Drew High School’s display at the county fair. He started work picking oranges.

He initially worked in the groves harvesting oranges and eventually worked his way up to truck driver and foreman.

“During the summer or whenever school was out, I could sometimes go to the grove with him,” Steib said. “Eventually, he decided he could do as good a job as anybody else was doing.”

After learning all he could about the agriculture business, he secured a $20,000 loan, which he paid back in one year, and started his own citrus transport company — Curtis Massey Harvesting — which employed 270 and operated with three tractors, nine trailers, 26 trucks and seven foremen.

In 1974, the year before he began his mayoral term, Curtis moved to Oakland, Florida. There, he met and married Edna Steplight Massey.

And even after his term as mayor was finished, he continued as a consultant to the commission.

“I would call and say I was coming over, and he said, ‘Well, I have a meeting with Oakland,’” Steib said. “He was very much into Oakland because he really liked living there and doing what he did as mayor. … He was sad that things were building up so much in Oakland. He wanted the properties to be an acre in size, not one on top of each other.”

Fifty years ago, the town had few paved roads, a two-man police department, no municipal taxes and no subdivisions.

ASSISTING IN THE AMERICAN DREAM

Massey had a fundamental love and care for mankind. His generosity and passion for helping others knew no bounds. Well after his tenure as mayor, he still was looking after the needs of the people of his community. He was a person who always helped others when he could, however he could, family members said. Having an innate drive and desire to see others prosper, he worked tirelessly to ensure the people of his community did not succumb to the poverty that plagued the black community in Oakland but had their stake in the American dream of home ownership.

“To be certain of such, he held mortgages for black residents when the banks would not loan them money, following in the footsteps of his dad, Frank Massey,” the family wrote in his obituary. “Many of his relatives and friends have been recipients of his generosity and kindness.”

“He didn’t expect anything back from people,” Steib said.

“As a father, he always wanted me to tell the truth,” she said. “He didn’t think there was anything he couldn’t hear that would bother him. He was very religious when I was young. He was superintendent of the church school at the Methodist church at the time in Oakland. We used to go to Bible study.

“He was a good person,” Steib said. “He used to train bird dogs, and I used to go with him, and it was enlightening to try to do those kinds of things. He was into all kinds of things, and he excelled at everything he tried.”

Massey retired at the age of 65 and would enjoy 33 years of retirement. Fishing became his passion and favorite pastime. He loved the peace and serenity of fishing in the local lakes. Even more, he enjoyed catching them and giving them away to family, friends and members of the community. After becoming frail and unable to go to the lake, not going fishing became the thing he missed most. Two days before his passing, he expressed to his grandson Brandon that he wanted to go fishing.

Massey also enjoyed taking cruises.

“He just was a man of leisure,” Steib said of her father’s retirement years.

Massey was preceded in death by his parents, Frank and Flossie Nelson Massey; son, Ricky Johnson; and brothers, David Massey, Lenwood Massey, Grant Massey and K. C. Massey.

Besides Steib, Massey is survived by another daughter, Gladys Rodgers Coates; stepdaughter, Rosalyn Jones; son-in-law, Joseph Steib; grandsons, Will Curtis Hall (Michelle), Vance Hall (Maria), Wendell Coates (DeAndre); granddaughters, Elenora Vernell Hall, Jasmine Coates, Renee Bowman; step-grandchildren, Kenya Holmes and Jade Holmes; 10 great-great-grandchildren, Brandon Joseph Hall, James Carlies III, Jordan Carlies, Brittany Ortiz, Ashley Reid, Joshua Robinson, Amon Hall, Jazz’men Hall, Amaya Hall, Ayumi Hall; numerous other grands and great-great-great-grands, as well as a host of nieces, nephews, cousins, other loving relatives and friends.

Marvin C. Zanders Funeral Home, Apopka, was in charge of arrangements. A graveside service was held Feb. 5 at Orlando Memorial Gardens, in Apopka.