City of Kissimmee attorney, community servant, husband, father of five, and grandfather of fourteen, Donald Smallwood, whose service to the City spanned over 3 decades — passed away peacefully on Thursday, January 20, 2022. He was 68.
Don was born on October 13th, 1953, to Roy Edward and Joan Pryor Smallwood in Dehue, West Virginia, a humble coal mining community. Wanting a better life for his family, Don’s father, Roy, relocated the family to Kissimmee in 1960. Don graduated from Osceola High School in 1971 and was a proud Kowboy fan for life. He graduated from FTU (UCF) in 1977 with a bachelor’s degree and in the same year married his first love and wife of nine years, Cheryl Kemp. In 1981 Don earned his Doctor of Jurisprudence from Samford University at Cumberland School of Law in Birmingham, Alabama—the only time he lived outside of Osceola County as an adult.

Don moved his family back to Kissimmee and began working for the state attorney’s office after law school. He formed a law partnership with his friend Nick Kelly in 1982 and also began working for the City of Kissimmee. Shortly after, Don found love again when he met Cinda, who Don claimed, “knocked him off his feet,” and they married in 1987.

Don was a man of impeccable character. He loved his family more than anything in the world and was an amazing mentor to not only myself but to anyone that needed his help.

Austin Blake

Assistant City Manager, City of Kissimmee

Don Smallwood Kissimmee
Don Smallwood Kissimmee
Don Smallwood Kissimmee

Don’s passion for his community and family led him to transition from private practice to public service. He began his journey as the city attorney of Kissimmee in 1991 and proudly served his community for more than 30 years. Over Don’s dedicated career he oversaw the drafting of 1,466 city ordinances that were adopted, in 2011 he was nominated President of The Florida Municipal Attorney Association which he considered a privilege and was awarded City Attorney of the Year in 2017.

Outside of work Don loved spending time with family and living life to the fullest. He was a man of faith, conviction, and strength who enjoyed listening and offering profound advice. He filled his time hunting with his eldest son, coaching his youngest son’s football and baseball teams, running alongside his children at their cross-country meets, watching his daughters dance, swim, and cheer competitions, and attending local high school football games. He was always drumming on the dashboard to his favorite music and even secretly took drum lessons. He enjoyed his peaceful rides on his Harley, working on model trains, and fixing up and racing “The El Camino”.

He was proud of his West Virginia heritage, loved cheering on the Mountaineers and the Florida State Seminoles. Ballroom dance with his wife, being surrounded by his grandchildren, playing cards with his sister and cousin, Sunday matinees, and Thursday night dinners with his dearest friends were just a few of the things Don cherished. 

Don is survived by his loving wife of 34 years Cinda R Smallwood whom Don often called, “heaven-sent”, his five children, Chad (Shannon) Smallwood, Courtney (Jamie) Nix, Cristen (Paul) Hardy, Ciara (Brent) Boate, and Cyle (Lelar) Smallwood and his fourteen grandchildren. He is also survived by his younger sister Susan Smallwood Wild. Don will be missed by many and Positively Osceola thanks him for his years of selfless dedication to the community.


Tuesday, January 25, 2022
5:00 PM to 7:00 PM
Conrad & Thompson Funeral Home
511 Emmett St
Kissimmee, FL 34741


Wednesday, January 26, 2022
11:00 AM
Cornerstone Family Church (Canoe Creek Rd. – St. Cloud, FL)