American and British sailors both sang this forebitter. Slavery was abolished in Jamaica and aboard British ships in 1807. Although slaving with American ships was prohibited by several acts of Congress between 1807 and 1823, shipmasters were convicted for this crime as late as 1861. Colcord believes this song most likely dates from somewhere between 1819 and 1825, when joint naval powers finally cleared the West Indies of pirates.

Captain Moore and Baltimore don't seem well-preserved in records, and the California clipper ship Flying Cloud was not built until 1851. Whall nevertheless feels this is the fast ship immortalized in song.

As far ships as official, properly authenticated records go, this was one of the fastest ships that ever floated. She was built by Donald M'Kay, of East Boston, U.S., in 1851. Her dimensions as then given were :—
Length of keel, 208 feet
Length of deck, 225 feet
Length over all from knight heads to taffrail, 235 feet
Extreme breadth of beam, 41 feet
Depth of hold, 21.5 feet
Tonnage per register, 1750 feet

The Flying Cloud only beats by a very narrow margin the equally celebrated Sovereign of the Seas from the same yard. Her day's run of 374 knots from noon to noon, taken from her log by Lieutenant Maury, and carefully corrected for longitude, is her best record. Maury gives the equivalent in land miles as 433.2 statute miles, and correcting this for her day (which was 24 hours, 19 minutes, 4 seconds), estimates it as equal to 427.5 statute miles for 24 hours. The Flying Cloud is credited with many remarkable passages ; for example, New York to San Francisco in 84 days.

Frank Shay and other authors have tried to clear her name: the Flying Cloud had no Captain Moore, was never engaged in the slave trade or piratical practices, and there are no records of another ship with the name. Stan Hugill's position was that because the slave-trading Flying Cloud and her captain had not been identified, both were probably fictitious.