Ebenezer Woodbury Franklin Stirrup, Sr. became the most successful African-American businessman in Coconut Grove, FL. History has mainly recorded the advances he made in real estate, but Stirrup was also a formidable businessman owning a grocery store, bicycle repair shop, tailor shop, meat market, private horse and buggy transportation, two cemeteries and a dry goods store. The dry goods store was owned in partnership with William Burdine, founder of the Burdines department store chain which was renamed Macy’s Florida in 2005 by the Federated Department Stores Inc. (now Macy’s, Inc). Through his years of hard work and business savvy, Stirrup eventually became the first black millionaire, owning a variety of properties in Coconut Grove, Cutler and Overtown. When he passed at the age of 84 in 1957, he was not only one of the largest landholders in Coconut Grove, but had also done much to improve the housing conditions of the African-American community in Miami.
Stirrup was born on Governors Harbour Island just off the coast of Eleuthera in the Bahamas in 1873. He was the child of his Bahamian mother and her wealthy white employer, from whom he took his last name, which was spelled Sturrup. At the age of nine, Stirrup was left in the care of relatives due to the untimely death of his mother. Determined to advance despite the odds, Stirrup saved his meager earnings and in 1888, at the age of 15, emigrated to Key West to live with an uncle. Under the tutelage of his uncle who was a carpenter, he learned the skills of woodworking and construction, which would prove extremely useful in the years to come.
Stirrup would remain in Key West for 10 years, but during that time he returned to the Bahamas to marry his childhood sweetheart, Charlotte Jane Sawyer. After becoming disenchanted with an arrangement made with his uncle, Stirrup modified his last name from Sturrup to Stirrup and moved to Cutler, a settlement 14 miles south of the mouth of the Miami River. There he worked in the pineapple fields by day and cleared land for home sites in the evening. In lieu of cash, Stirrup was often paid in land, the source of what would become a vast accumulation of valuable real estate. The first of the 10 Stirrup children (six of whom survived into adulthood), named Kate Biscayne, was born in Cutler.
In 1899, when he was 25, Stirrup moved the family to Coconut Grove, where he was employed by James Deering as both a chauffeur and a farm worker on Deering’s magnificent estate, Villa Vizcaya. (Other sources indicate that Stirrup worked for Charles Deering and even others give his employer as William Deering, the father of James and Charles). Eventually, Stirrup’s land holdings increased and when Coconut Grove pioneer John Frow offered to sell land in Coconut Grove, Stirrup was in a position to purchase a significant number of lots. Stirrup and his wife began to construct frame houses to rent to other Bahamians who were immigrating to South Florida. The houses were built of sturdy Dade County pine, and were simple structures based on Bahamian housing types. Stirrup and his wife, who was employed as a laundress, built the homes together at night after a full day’s labor. In a 1976 interview, Kate Stirrup Dean, the eldest daughter, recalled her father’s views on home ownership, “Father believed in every family having a house, a yard and a garden, so you would feel like you had a home. He felt that people became better citizens when they owned their own homes.”
Stirrup constructed more than 100 homes in his lifetime, providing an opportunity for newly arrived Bahamians to actually own their first home. Many of the houses built by Stirrup remain, and are concentrated around Charles Avenue (originally Evangelist Street) close to the present-day Coconut Grove Playhouse, and the heart of the Bahamian community. Stirrup’s own home is at the head of Charles Avenue, and has survived as a legacy to its builder. Over the years, many across Miami have continued to honor the legacy of Stirrup by keeping his memory alive in books as well as naming buildings around the city after him, like E.W.F. Stirrup Elementary in West Miami, The Stirrup Townhouses, and the Stirrup Senior residences in Coconut Grove. His residence, which still stands today, as well as the street he cleared to serve as the major thoroughfare for the community, Charles Avenue, were both designated Historic Sites by the City of Miami.