The ring was an American scandal, broken in May 1875, involving the diversion of tax revenues in a conspiracy among government agents, politicians, whiskey distillers, and distributors.
The kingpin of the Whiskey Ring was the notorious General John McDonald, whom Grant had appointed Revenue Collector of Missouri District in 1869.
McDonald was indicted, put on trial, found guilty, fined $5,000, and sentenced to federal prison for 18 months.
In 1880, an angered McDonald authored a salacious book The Secrets of the Great Whiskey Ring, in an effort to keep Grant from getting a third term nomination.
[3] By the mid-1870s, during the Ulysses S. Grant administration, the illegal cartel had organized into an efficient machine of whiskey distillers who kept Treasury agents in line by aggressive tactics.
[3] The whiskey syndicate involved distillers, government officials, rectifiers, gaugers, storekeepers, and internal revenue agents.
In St. Louis, the ring was led by Missouri Revenue Collector John McDonald, appointed by President Ulysses S. Grant, in 1869.
McDonald coordinated with Grant's private secretary, Orville Babcock, in Washington D.C. to keep the ring hidden and prevent it being exposed.
George Fishback, the proprietor of the St. Louis Democrat, gave Bristow and Wilson an informant to investigate the Ring and uncover illegal activity.
The secret investigators reported to Bristow evidence of a massive ring of conspirators between revenue agents and distillers.
The ringleader John McDonald, was indicted, tried by Henderson and United States Attorney of the Eastern District of Missouri, David P. Dyer.
"[16] Grant, on the other hand, was divided between the loyalty he had for Babcock, and his desire for Bristow and Pierrepont, trustworthy members of his cabinet, to prosecute the Whiskey Ring.
[11] Since Babcock had no acceptable explanation for his messages, he was indicted for conspiracy to defraud the Treasury of the United States on November 4, 1875.
[20] It took place at the U.S. Post Office and Customs House located at 218 North Third Street, and the status of the defendant made the trial a popular and well-attended spectacle.
[19] When court was not in session, Babcock stayed at the newly rebuilt Lindell Hotel on Sixth Street and Washington Avenue.
[19] Grant's White House deposition took place on February 12; it was notarized by Chief Justice Morrison Waite and witnessed by both Bristow and Pierrepont.
"[19] Grant's deposition, Sherman's in-person testimony, and the evidence presented by Babcock's shrewd defense counsel led to his acquittal on February 25.
[25] The Whiskey Ring was seen by many as a sign of corruption under the Republican governments that took power across the nation following the American Civil War.
The Whiskey Ring, along with other alleged abuses of power by the Republican party, contributed to a national weariness of Reconstruction, which ended Grant's presidency with the Compromise of 1877.
McDonald said that when Babcock had attended the annual St. Louis Fair, with Col. John A. Joyce, while they were walking on 5th Street, he saw a very attractive woman, who would be nicknamed the "Sylph" for her beauty.
Babcock reportedly said to Joyce, "She is the most beautiful and bewitching woman I ever saw; for heaven's sake; let us turn the corner and meet her again so that you can give me an introduction.".