[4] Skipwith assisted Robert Livingston (known as "The Chancellor" for the high New York state legal office he held) in negotiating the Louisiana Purchase, and actively participated in the transfer of 828,000 square miles of land in its southern part.

[6] At first, Skipwith and the West Florida government – located in St. Francisville – were opposed to the proclamation, preferring to negotiate terms to join the Union as a separate state.

However, the Territory of Orleans Governor, William C. C. Claiborne, who led armed troops to take possession in December 1810, refused to acknowledge the legitimacy of the West Florida government.

In December 1814, during the War of 1812, Magloire Guichard and Skipwith sponsored a legislative resolution to grant amnesty to "the privateers lately resorting to Barataria, who might be deterred from offering their services for fear of prosecution."

In 1827, Skipwith, Armand Duplantier, Antoine Blanc, Thomas B. Robertson, and Sebastien Hiriart received permission from the Louisiana State Legislature to organize a corporation called the Agricultural Society of Baton Rouge.