The phrase “until Hell freezes over” seems to originate during the civil war, as the earliest examples in print date from that time. In his 1869 book, The Life and Campaigns of General U.S. Grant, from Boyhood to his Inauguration as President of the United States, Phineas Camp Headley puts the phrase in the mouth of a boastful rebel soldier during Grant’s first effort to capture the Confederate stronghold of Vicksburg, Mississippi; the dialogue takes place on December 29, 1862:

During Monday, the 29th, several brilliant charges were made on the works; but all was in vain; the [Union Army] men were outnumbered by the enemy, and could not hold the positions, even after they were taken. General Blair’s brigade, led by, himself, on foot, particularly distinguished itself, and suffered the greatest loss. As the men, swept down by the iron and leaden hail, fell back, the last of the brigade lingering behind in the storm was its commander.

After hostilities had ceased, and the slain and wounded were borne away under a flag of trace, the pickets had their talk:

“How far is it to Vicksburg?”

Rebel picket. “So far you’ll never git thar”

Federal picket. “How many men have you got?”

Rebel picket. “Enough to clean you out.”

Then another rebel, who seemed to be the stump speaker of the squad, with a flourish, added:

“Banks has been whipped out at Port Hudson, Memphis has been retaken, and you Yankees will not take Vicksburg till hell freezes over.”

And so the conversation went on during the four hours of truce. The profane assertion of the rebel was destined to be refuted in the heat of the next midsummer.

In an 1865 profile of Grant in Harper’s New Monthly Magazine, the phase is attributed to Gordon Granger in a comparison of the persistence and tenacity of Union generals:

It is difficult to say which excels in these qualities. Grant’s famous dispatch from Spottsylvania, “I propose to fight it out on this line if it takes all summer,” was written with compressed lips—the reader naturally reads it with clenched teeth—and fairly and graphically illustrates the perseverance and stubbornness of the man. It is even more forcible than the memorable dispatch of Thomas, “We will hold Chattanooga till we starve”; and in better taste than that of Granger’s, ” I am in possession of Knoxville, and shall hold it till hell freezes over.”

This would date Granger’s use of the phrase to 1863, as that’s when Knoxville fell to the Union army.

Image: John Collier: The Devil Skating when Hell Freezes Over (2012)