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Myra A. Jones. (Aunt Myra)
Billy was like another nephew. to me calling me "Aunt Myra". He was always a special kid who kept the sweet side of himself hidden only revealing the macho side but we that knew him know kind he was. Being a big. Gator fan I insisted he remove. his FSU cap before I would hug him. He was a unique person and will be missed by everyone who knew him.
Myra A. Jones. (Aunt Myra)
Billy was always like another nephew to me calling me "Aunt Myra". He was always a special kid and enjoyed hiding the sweet side of him prefering
David Drake
Billy you were one of a kind! Great LEO and friend. I’m glad I got to be one of your Chaplains at NCSO. Thanks for your service and the memories.
Kathie J Sciullo
My condolences to family, friends and loved ones of Billy. He was fun to know in high school . He will be missed by his FBHS classmates.
Holly T Lowe
We have know Billy for over 30 years. When my hubby was FTO for Billy he came by to eat when they worked night shift. One of kind and truly a gentle giant. He will be missed by all.
Cedric Arline
To my good friend, he was someone you looked up to. He had his “Grumpy Bear” moments, and we loved him for being him. I wish you a peaceful, and pleasant rest my friend. Your work here is complete and you’ve left lifelong legacy with an abundance of memories. Love you Buddy!
Brandon Smith
Josh Askew
Billy was always such a wonderful human being and amazing to work with at NCSO. I know you are resting in peace with the good Lord brother.
Josh Paetsch
Billy was a fixture in this community. A lot of us local law enforcement always looked up to him. He was one hell of a cop and even more of a man. Words cannot express how grateful we all are to have known him and spend time with him. He was often referred to as “Grumpy Bear”, but he always had a heart of gold and truly loved helping others. God bless you my brother and we’ll see you again.
Sheri Miranda
You will be missed,my brother from another mother .. always the fond memories of our family hanging out together growing up. us running the streets of Fernandina Beach you and my brother on bicycles. you is a long time neighbor always asking me Ms. Sheri you doing ok? always making sure my children are safe as they were growing up! you will be very missed! God's got you now! time to rest my friend!
Jill Zuber McCarthy
Pete "Da Meat" Silvano
There's so much I can say about Billy. Him and I were business partners well over 10 years ago in The hospitality business. we had a café inside the courthouse and a kitchen inside of Wicked Davies downtown. We also entered barbecue competitions and did a ton of catering within the sheriffs department and beyond. I learned a lot of skills in the barbecue genre from Billy and by far he had the best brisket I've ever had. I can actually replicate it and I thank him for it very much. I also rented from him for a little while when I was getting on my feet. He was a very humble individual and very quiet. He had a different type of humor, but one of the biggest hearts of anyone I know. He would give me the T-shirt off his back if necessary. When Billy meant business he met business but all in all he was the kindest gentle giant around. I will miss you so much, buddy and I wish I had seen you the last time I was in town. Kids also said rest in peace, Mr. Billy, as that's what they called you. Take care and God bless you and your family. .
Cody
I had the privilege of being around Billy a handful of times over the years and always enjoyed time spent together. What I missed in getting to know him more was made up by the countless stories shared with me of he and his closest buddies throughout their decades of friendship. Billy—as its been illustrated—was a bold and strong individual. He was also immensely loyal and always there when his friends needed him, never fearful of what laid ahead. Billy’s family and friends will be in my thoughts over the coming weeks.
Mitch May
Prayers to the family and all who were close to Billy. He touched many lives, and will always be remembered for helping people. Billy was a great friend and classmate. He will aways be remembered in our hearts! RIP Billy!
William "Billy" J. O'Leary, Jr.
2025-05-19
William “Billy” J. O’Leary, Jr., 62, passed away unexpectedly Monday, May 19, 2025.
Billy began his life in Fernandina Beach as the son of the late William J. and Roberta Pearce O’Leary.
Billy was a proud graduate of Fernandina Beach High School where he played football, baseball, wrestling and threw the shot putt for the track team. Billy played most sports from the Peewee age all the way through high school. After high school, he attended Newberry College in South Carolina on a football scholarship.
He also served honorably in the U. S. Marine Corps before returning to Fernandina Beach where he served his community for 30 years in law enforcement. His service began with the Fernandina Beach Police Department and he retired from the Nassau County Sheriff's Office with 24 years’ service.
Billy was genuinely a fixture of the Fernandina Beach community. In addition to being a dedicated alumni of Fernandina Beach High School he served as president of the Quarterback Club, he was the “Voice of the Pirates” for both football and baseball. He coached football in the community and was heavily involved in the fundraising and supporting the various teams at FBHS.
Billy was a die-hard FSU fan. He loved all things FSU. He also loved to barbeque. In addition to catering, he cooked for many fundraisers over the years and also participated in barbeque competitions where he won awards.
He leaves behind his children, Emery McTindal of Charlotte, NC, Caitlin (Eric) Lee of Fernandina Beach and Skyler (Dynasty) O’Leary of Hilliard; his sister, Robin (Billy) Holland of Tishomingo, MS; his “best ex-wife” Carla Cribb of Fernandina Beach; his beloved grandchildren, Carter, Brooks and Parker Mae and a niece and nephew, Angela Stroupe and David Holland.
A celebration of Billy’s life will begin at 2:00 PM on Wednesday, May 28, 2025 at the Journey Church. The family askes that all who attend dress “Billy casual”.
Billy will be laid to rest at a later date.
Rather than flowers, please make donations, in Billy’s memory, to the FBHS Quarterback Club, P. O. Box 16331, Fernandina Beach, FL 32035 or through the First Port City Bank in Fernandina Beach.
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