A key strategist who worked closely with John D. Rockefeller building the Standard Oil Trust, Flagler noted both great potential and a lack of services during his stay at St. Augustine.

Ball claimed the company could not afford the same costs as larger Class 1 railroads and needed to invest saved funds in its infrastructure, the condition of which was fast becoming a safety issue.

The FEC was historically a Class I railroad owned by Florida East Coast Industries (FECI) from 2000 to 2016, FOXX Holdings between 1983 and 2000, and the St. Joe Company prior to 1983.

Though Flagler remained on the Board of Directors of Standard Oil, he gave up his day-to-day involvement in the firm in order to pursue his Florida interests.

Construction began in 1889 and the bridge opened on January 5, 1890, allowing a direct connection for private railcars and Pullman coaches to reach St.

Finally, Flagler acquired the St. Johns and Halifax River Railroad which opened in the early 1880s from East Palatka southeast to Ormond Beach and Daytona.

Flagler would eventually claim in excess of two million acres (809,371 ha; 8,094 km2) for building his railroad, and land development and trading would become one of his most profitable endeavors.

The development of these three structures, coupled with railroad access to them, established Palm Beach as a winter resort for the wealthy members of America's Gilded Age.

He sent his two lieutenants, James E. Ingraham and Joseph R. Parrott—now famous in Florida history—to investigate; they brought boxes of truck (produce) and citrus back to Flagler, who then wired Tuttle, asking, "Madam, what is it that you propose?"

Tuttle added 50 acres (200,000 m2) for shops and yards if Flagler would extend his railroad to the shores of Biscayne Bay and build one of his great hotels.

To further develop the area surrounding the Miami railroad station, Flagler dredged a channel, built streets and The Royal Palm Hotel, instituted the first water and power systems, and financed the town's first newspaper, the Metropolis.

In 1903, Flagler extended the main line an additional 12 miles from Downtown Miami southwest to access much of the unsettled lowlands near Cutler Ridge which he felt could generate agricultural traffic.

[10] According to historian Joe Knetsch, reformers and muckrakers exaggerated charges of peonage regarding construction of the Florida East Coast Railway in 1893 to 1909.

[8]: 100  In 1925, the Moultrie Cutoff was built to shorten the distance between St. Augustine and Bunnell (just north of Ormond Beach) on the main line by bypassing its turn towards Palatka.

Ball was certain that if the company didn't become profitable, the equipment and track would deteriorate to the point where some lines would become unsafe or unusable and require partial abandonment.

Ball's use of replacement workers to keep the railroad running during the strike led to violence by strikers that included shootings and bombings; a number of freight trains were derailed or blown up.

[23][1] Eventually, federal intervention helped quell the violence, and the railroad's right to operate during the strike with replacement workers was affirmed by the United States Supreme Court.

The FEC continued operation with heavily reduced non-union crews (often former strikers), at the cost of a high turnover rate, low morale, and deteriorating infrastructure.

The Florida East Coast Railway has operated from its relocated headquarters in Jacksonville since it sold the original General Office Building in St. Augustine to Flagler College in late 2006.

In March 2005, Robert Anestis stepped down as CEO of Florida East Coast Industries after a four-year stint, allowing Adolfo Henriquez to assume that position, with John D. McPherson, a long-time railroad man, continuing as president of the railway itself.

[31] James Hertwig retired as president and chief executive officer of the company effective December 31, 2017, and was replaced by Nathan Asplund as the railway was purchased by Grupo México and now manages it along with its other transport interests.

A new railway extension to Orlando International Airport started service in 2023, and a future rail expansion to Tampa is currently in the planning stages.

Additionally, the FEC currently transports Tropicana Products "Juice Train" cars to and from one of the company's processing facilities located on the "K" Line.

The Juice Train concept was developed by Tropicana founder Anthony T. Rossi in conjunction with Seaboard Coast Line Railroad (a CSX predecessor) beginning in 1970.

At its greatest extent, Florida East Coast Railway's Main Line ran from Jacksonville via Miami to Key West, a distance of over 500 miles.

In 1925, the Moultrie Cutoff was built to reroute the main line on to a more direct route from St. Augustine to Bunnell, bypassing the inland swing to East Palatka.

[48] In 1972, four years after the discontinuation of FEC's passenger services, work began to restore the main line to single track with passing sidings every 10 miles and Centralized traffic control.

A steam locomotive pulled the first train over the line onto the wharf on the Indian River at Titusville on the afternoon of December 30, 1885, and greatly accelerated the transportation of passengers, produce, seafood, and supplies to and from central Florida.

While Titusville thrived thanks to this new transportation connection, Enterprise lost stature as a steamboat port, since Henry Plant's railroad paralleled the St. Johns River and greatly reduced travel times to Jacksonville.

[65] The branch would also run past The Casements, which would be the winter home of John D. Rockefeller, the founder of Standard Oil and Flagler's former business partner.