It began in 1939 as the Henry M. Flagler, a regional service between Miami and Jacksonville, Florida; the FEC renamed it and extended it to Chicago a year later.

As an overnight streamliner it was part of the every-third-day pool shared by the City of Miami and South Wind.

Together with its counterparts the South Wind and City of Miami, the trains offered daily service between Chicago and the east coast of Florida.

[3][4] As a daytime streamliner, the Henry M. Flagler operated entirely over the Florida East Coast Railway, however, this particular train ended in 1940.

[5] At Jacksonville it had sections that split and joined with the ACL's West Coast Champion and went to Sarasota via Orlando and Tampa, and St. Petersburg via Gainesville.

[6] Separate connecting Atlantic Coast Line branches from Jacksonville served Gainesville, Orlando, Tampa, St. Petersburg, Sarasota and Ft. Myers.