[citation needed] He was to be re-elected three times; he resigned on October 2, 1798, on the grounds of ill health and in disgust at the Alien and Sedition Acts.

Working with Jefferson and Madison, he introduced three sets of resolutions in 1793, which attempted to censure Hamilton's "administration of finances" as Secretary of the Treasury to the point of accusing him of maladministration in office under the Funding Act of 1790 to force the US to repay America's debts to France following the French Revolution.

He, however, published opinion pieces and columns, chiefly in the Richmond, Virginia, Enquirer, in which he deplored the Era of Good Feelings as false prosperity, given over to banks, tariffs, and fraudulent internal improvements; these would centralize and corrupt government, and ruin the farmers.

From the governorship, Giles encouraged Virginia's Senator Littleton Waller Tazewell to organize a southern resistance to the American System of Henry Clay centered on a boycott on northern manufactures.

Giles lost to some extent: while the governor's term remained short and was still accountable to the General Assembly, the Constitution of 1830 abolished the privy council, thus making the governorship a bit more independent.

Frederick Scott Oliver called him a "preposterous, pugilistic character" marked by a "reckless disregard of truth" and by "the grossness of his nature.

"[2] Joseph Story, though taking similar umbrage at Giles's alleged rhetorical excesses and noting the poor impression made by his dowdy appearance, wrote that, "when he speaks, your opinion immediately changes":[A] clear, nervous expression, a well-digested and powerful condensation of language, give to the continual flow of his thoughts an uninterrupted impression.

He holds his subject always before him, and surveys it with untiring eyes; he points his objections with calculated force, and sustains his positions with penetrating and wary argument.

He certainly possesses great natural strength of mind; and if he reasons on false principles or with sophistic evasions, he always brings to his subject a weight of thought, which can be shaken or disturbed only by the attack of superior wisdom.

[3]Claude Bowers called Oliver's appraisal a "wretchedly unfair caricature" and advanced a favorable view, noting, among other things, praise that Giles received from Patrick Henry, John Randolph of Roanoke, and other contemporaries.