A tycoon and a train transformed The Sunshine State

If there was one man who pretty much created modern Florida it was Henry Flagler. Flagler (1830-1913) made a fortune in the oil business and was one of the world’s richest men when he embarked on a second career that transformed Florida from a semitropical wilderness into a powerhouse of tourism and real estate development.

The Gilded Age magnate first visited Florida in 1878 when he wintered in Jacksonville to improve the failing health of his first wife, who died only a few years later. But he was charmed by the state’s weather, and soon smelled opportunity amid the orange blossoms. Frustrated by the lack of good accommodations and transportation, in 1885 Flagler began work on the lavish 540-room Ponce de Leon Hotel in St. Augustine, then bought two railroads and formed a new company that would become Florida East Coast Railway — the predecessor to Brightline.

Flagler spent the next quarter century enticing northern tourists to visit Florida by plowing money into railroads, resorts, a steamship line, land companies, newspapers and cities along the state’s east coast from Jacksonville to Key West. “He was building transit-oriented development 100 years before the term was used,” said Jim Kovalsky, president of Florida East Coast Railway Society, a group of fans devoted to the history the railroad.

Beginning in 1892, Flagler obtained a grant from the state of Florida awarding him 8,000 acres per mile for extending his line south of Daytona, allowing new cities like New Smyrna, Titusville and West Palm Beach to develop. In April 1896, the railroad reached Miami, then home to only a few hundred souls, and as he had in other places he built streets, water and power systems, a resort hotel, schools, churches and houses for workers. He drained canals from the Everglades that covered much of the land and Miami soon had the first of many real estate booms. In 1905, he began his last and least successful endeavor to extend the railroad over open water to Key West, an ill-advised effort to capitalize on increased trade brought by the opening of the Panama Canal. Hundreds of men died during the construction of “Flagler’s Folly,” which was completed a year before Flagler died in 1913. In 1935, a category 5 Labor Day hurricane — still the most powerful storm to strike Florida — mangled the Overseas Railway and the company sold its infrastructure to the state and Monroe County, which built a highway over the old route.

In the ensuing years, as U.S. rail travel suffered a death at the hands of the automobile, Florida East Coast discontinued passenger service. Flagler’s old company fell in and out of bankruptcy but chugged along as a real estate development and freight rail enterprise. In 2007, New York-based private equity firm Fortress Investment Group paid $3.5 billion for the company with a strategy of reaping money from the railroad’s old assets. Fortress sold Florida East Coast Railway for $2.1 billion to Grupo Mexico but retained its similarly named parent, Florida East Coast Industries, and exclusive rights to run passenger service over the tracks.

Launched in 2018, Brightline represents the first privately funded major U.S. intercity passenger rail service in over a century (read “Now boarding“). It projects in 2025 it will capture 4.3 million U.S. and international rail passengers traveling between South Florida and Orlando, according to a statement for a $770 million bond offering. Brightline also plans to expand to Tampa with stops at the Orange County Convention Center and near theme parks.

In an interview on CNBC, Fortress co-founder Wes Edens, a part-owner of the NBA’s Milwaukee Bucks, said Brightline’s niche is to exploit major city pairs roughly 250 miles apart. A sister firm, Brightline West, plans a $12 billion high-speed train to link Los Angeles and Las Vegas. Count Edens among the fans of Flagler. He reportedly read “Last Train to Paradise: Henry Flagler and the Spectacular Rise and Fall of the Railroad that Crossed an Ocean,” an account of Flagler and his railroad. “I found it compelling on many levels, not the least of which was that he was doing something that nobody else had done before and doing it in a way that was profoundly impactful,” Edens told the Orlando Sentinel.