Oscar Sunny Shipley

Oscar Sunny Shipley, 89, passed away peacefully surrounded by his family in Kissimmee, Florida on September 15, 2023. Oscar was born in Georgetown Kentucky to parents Dias and Annie Shipley on September 1, 1934.

He lived a very active and full life. He was a proud Air Force veteran. He loved his career as a horse trainer, and was very proud of his work, often recounting stories of his horses and their races and the time he put into them and their accomplishments. He met his wife of nearly 56 years, Helen, during his horse training years, and they got married on September 23, 1967. They had three children together: Carl, Oscar and Jennifer. They lived on a farm for a while, and he loved telling stories of their milk goat and more until finally they moved to Florida and built their life and final home here where they lived for 47 years.

This is where Oscar became a large part of the community. He retired from the city of Kissimmee. He became a regular in many small mom and pop stores and made a difference wherever he went, loving to make small talk with whoever he could along the way. He was active in the Little League program here, and boy did he love his sports, especially softball and baseball. He would watch all the Little League he could all day long. While he loved sports, his real passion was fishing. Anyone who knew Oscar knew his happy place was on the lake. He took great pride in his fishing career, and has many awards, magazine clippings and newspaper articles to show for it. He knew the best spots to fish, the best lures to use and would often snag Helen’s nail polish to make a lure just right for what he needed it to do. For him, fishing wasn’t just a passion but a way of life, one he shared with his friends and family.

Oscar was preceded in death by his parents and eleven of his twelve siblings. He is survived by his wife, Helen; his sister Maxine Collins; his children, Oscar, Carl, and Jennifer; his grandchildren, Kayla, Tara and Kassandra; and great-grandchildren.

His memorial service will be held at Conrad and Thompson Funeral Home on Friday September 22, from 5:30 p.m. until 9 p.m. located at 511 W Emmett St, Kissimmee Florida 34741. Oscar will be accorded Military Honors by the Osceola County Veterans Council.

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