O.B. OSCEOLA, SR Collier County Born, Our Living Legacy”

By Tina Osceola

Today’s Ochopee, Florida bares little resemblance to its former 1934 self, when it was some what of a hub of Florida’s early agribusiness. Large wooden packing houses where tomatoes were boxed up, placed on trucks and sent off for parts unknown.

Most of the Seminole families who lived in that area worked the fields and were an integral part of the workforce.

Villages were dotted along the canal banks of the Tamiami Trail and were as common as a sunning alligator.

In what is now a campground in the Big Cypress National Preserve, a Seminole family had set up their village close enough to the hustle and bustle of the farms of Ochopee, but far enough so that they were able to still remain within a few hours of Miami, where other family were living and working.

Cory and Juanita Osceola and their three older children, Tahama, Curtis and Petties moved to this spot in the early 1930’s. In March of 1934, Juanita gave birth to her fourth child, a son they would name after a Miami attorney, Oscar Bryant “O.B.” White, who represented the Seminoles fighting the federal Indian policies of that era.

O.B. was the only child not born in a hospital. Juanita happened to be alone in the camp when she went into labor and delivered O.B. by herself. Their bond was strong throughout the rest of Juanita’s life.

The family moved their village many times throughout young O.B.’s childhood, following work and opportunity. As a child O.B. worked in the fields hauling buckets of water to the farm workers, picking tomatoes, and loading boxes, even driving farm trucks before he was twelve years old.

He entered school for the first time in Everglades City with his younger brother, Guy, younger sister, Mary, and his cousin, Harry Billie.

O.B. was a teenager when he first stepped into his first grade classroom. He was a quick learner, good in school and like his brother and cousin, he excelled in sports.

Entering school for the first time as a Seminole in the South during those years of Jim Crow and segregation produced unique and an often untold historic perspective. O.B. has great memories and lifetime friends from that era but the scars of having to sit on the bus when his white friends would go into eat, or not being allowed into restaurants are everlasting.

His friend, “Punch” Herren, would bring soda and snacks back out to the bus. The silver lining were the good people of Everglades City who took him into their homes and families.

O.B. went on to serve in the US Army, only to return on an honorable hardship discharge due to the death of his older brother, Curtis. Upon his return he worked in Naples and eventually trained to become an air condition repair technician for Stevenson Heating and Cooling.

Many in Naples know O.B. as the winning stock car driver of the infamous “Zero,” a black 1957 Chevy.

All of this provides a cursory background for a man who has become legendary in many ways. He will be 85 years old this March and he still works as hard as he did when he was a boy.

Up until this last year he was still building chickee bars. Now he travels the state setting up a booth with his daughter, Tina Marie Osceola, and granddaughter, Dakota Osceola, selling jewelry, sofkee corn that he grinds himself as well as traditional corn pounders that he carves out of oak and cypress.

He also repairs and restores antique Singer sewing machines and searches for vintage cast aluminum cookware still in high demand by the Seminole women. He is known to frequent O.B. III’s (his grandson) baseball games, and a few NASCAR races with his son, O.B., Jr.

O.B. lives in Golden Gate with his wife of 52 years, Joanne Yannaco Osceola. They are the proud grandparents of five grandchildren and one great granddaughter. Most days you will find O.B. working in the backyard or navigating the aisles of the local hardware store. Regardless, this man is always working to support his family and to make sure he leaves a legacy.

4 replies
  1. David McCormick
    David McCormick says:

    O.B. and my father? Harvey McCormick were good friends and I can remember when they use to live in the village by Rattle Snake Hammock.

  2. Jim Coletta
    Jim Coletta says:

    Great article about a local legend. OB is also an astute business man who played a major role in the success of the Seminole casino in Immokalee. Proud to call him my friend.

  3. Carla Hasse Dean
    Carla Hasse Dean says:

    OB Osceola doesn’t have to work to leave a legacy. He’s a true legend.
    I know my dad, Max Hasse, thought highly of OB & truly considered him a friend. I still have & treasure several things OB gave my dad & will always value them as a gift of friendship. Be well, sir!


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