President Monroe also participated in the popular and lucrative practice of selling his slaves "down river" to plantation owners, in his case to Florida. Since the importation of slaves from Africa became illegal in 1808, there was a shortage of field labor in the south, just at the time when the industries of rice and cotton were expanding. The effect of submitting these workers to sunrise-to-sunset working conditions in the southern climate was debilitating and often led to disease and death. Such was the case with Monroe's slaves exported to Florida.

Monroe's slaves in the White House included three women: Sucky, Eve, Betsey, four men: Daniel, Tom, Peter, Hartford, an unnamed woman and 5 unnamed men

As Governor of Virginia from 1799 to 1802, Monroe oversaw the hanging of 27 slaves who conspired to gain their freedom. The leader was the 25 year old blacksmith Gabriel Prosser, hanged in October of 1800. The rebellion led to further tightening of laws regarding educating slaves, notably the "anti-literacy" laws. A proclamation by one of those executed slaves was a paraphrase of Patrick Henry, "Give me Death or Give me Liberty".

See Death or Liberty: African Americans and Revolutionary America Douglas R. Egerton, 2009