The senior Dennehy was born in County Kerry, Ireland, in 1834 and emigrated to the United States in 1851 when he was 17 years old. Three years later, about 1854, he came to Chicago and apparently served an apprenticeship in the liquor industry of that Illinois clity. In about 1855 he married Annie Mead Coogan, herself Irish-born in County Wicklow. They were wed in Chicago.
In 1870 having saved sufficiently to begin his own whiskey business, Charles Dennehy joined a partner named Weadley and they opened their doors at 15 Dearborn Street. That same year the U.S. census taker found Dennehy living with his wife in Ward 18 of Chicago. With them in their home were four children, Eleanor, 13; Thomas, 11; Anna, 9, and James, 9, and Charles’ 78-year-old mother. Three years later, in 1873, Weadley & Dennehy took a third partner named Cleary. Subsequently the company, now named Weadley, Dennehy & Cleary, moved to several addresses on South Water Street.
In the meantime Dennehy was carving out a political career in Chicago. As recounted in a 1874 book by M. L. Ahern entitled, “The Great Revolution,” the Irish immigrant was cited as a prominent force in the formation of the People’ s Party of Cook County. This organization was assembled with purpose of defeating ‘”starched collar” Republicans. At least for a brief period the People’s Party was able to unite politically groups that rarely got along, including native-born liberals, Irish, and Germans. One unifying factor was the growing Prohibitionist factor among the GOP. The Drys moved to ban the sale of liquor on Sunday in Chicago. They were characterized by Dennehy and his cohorts as “Puritan rule.”
Charles was among the candidates placed on the ballot in 1873 by the new political entity. Proposed for City Assessor, he ran strongly and was elected along with the entire Peoples Party ticket. In his book Ahern commented about Dennehy: “...No better selection could have been made for the discharge of the important duties of the office to which he has been elected....His knowledge of real estate and his unblemished character preeminently qualify him for the very responsible position to which he has been so handsomely elected by the people.” There is no record of Dennehy being elected to a second term as his party eventually dissolved.
In 1881, Dennehy and his partners split. Weadley and Cleary moved to River Street and continued in business. Dennehy, now on his own, stayed on South Water with a liquor dealership he called Charles Dennehy & Co. The reason for the break-up may have been Charles’ interest in bringing his son Thomas into the business. Thomas quickly became an officer in the newly formed company.
As blenders and compounders of whiskey as well as a wholesaler, the Dennehys featured a number of house brands, including "1901,” "Cherry Lane,” "Clear Spring,” "Jefferson Club,” "Old Carlton,” "Old Potter, " and "Pebble - Ford." In 1906 they trademarked Cherry Lane, Jefferson Club, Old Potter, and Pebble-Ford. Far and away the Dennehy flagship brand was “Old Underoof,” trademarked in 1905. The firm packaged that whiskey in both flask and quart sizes, usually in amber bottles bearing several label varieties. Frequently, as shown here, the bottles were embossed with his company name.
Widely acclaimed for his honesty, industry, business tact and for having accumulated a “liberal fortune” in the whiskey trade, Charles died in 1892. At that point Thomas Dennehy, without changing the company name, took over its full management. He proved to have a flair for advertising and its attendant puffery. An example is a booklet issued by the younger Dennehy that was printed on paper made to look like birch bark and held together by a leather thong. This city of Chicago-made whiskey was identified with an Indian chief, indicated as Old Un-Der-Oof, whose visage appeared on the cover along with a list of advantages the chief claimed for Dennehy whiskey. A newsletter of the advertising trade in 1901 hailed the publication as “a wonderful little book” and extolled it highly: “The lettering and the pictures have a decidedly aboriginal air -- tepees, wampum belts, tomahawks, moccasins, mustangs and campfire being depicted on the leaves of bark with the hot point of an old hunting knife....”
This Dennehy does not seem to have camped on Indian ground very long. By 1907 he was advertising in newspapers as far away as Spokane Washington using colonial American figures -- the people who drove out the Indians. Now Old Underoof Rye was “a particular whiskey for particular people.” Some ads claimed the whiskey was “almost entirely free” of fusel oil and tanic (sic) acid. Fusel oil should not be confused with fuel oil. It is not oil but an alcohol and a byproduct of making whiskey. It was believed to contribute to hangovers and distillers of good liquor tried to eliminate it.
Thomas Dennehy hit his stride several years later. He conceived of a series of ads in Chicago newspapers keyed to what was happening with the Chicago Cubs baseball team. Although Cubs fans have not had much to cheer about for almost a century since, the club was in its heyday in 1910. It had won the World Series in 1907 and 1908 and although coming in second in 1909 had compiled a record of 104 wins against only 49 losses. When the team sparkled in 1910 and gained the World Series again, Dennehy hired local cartoonists to craft ads that discussed the contests.
One cartoon, entitled “Still in the Game,” showed a bear holding an elephant gun with four spent shells on the ground. They represented the four pitchers who had given up 13 runs in the two previous Series games to the Philadelphia Athletics. The Cubs lost a third game, occasioning a cartoon entitled, “No They Are Not Dead.” The Chicagoans won the fourth game by one run in extra innings and then lost the next and the Series. Undaunted for opening day 1911, Old Underoof was back and optimistic about the season. It would be 108 years, however, until the Cubs would win their next World Series in 2016.
Although not a politician like his father, Thomas Dennehy was an active member of liquor industry organizations both in Chicago and nationally. He became an elected board member of the National Wholesale Liquor Dealers Association. Perhaps emboldened by his prominence in the trade, in 1898 he challenged the powerful Distilling & Cattle Feeding Company, better known as the “Whiskey Trust.” Rectifiers were dependent on supplies of spirits from distillers, many of whom had been bought up by the Trust who then jacked up prices to wholesale dealers and rectifiers like Dennehy. Resentment ran high.
When an Illinois court decision in 1898 branded the Distilling & Cattlefeeding Co. as “an unjust monopoly” and determined that its business practices were illegal Thomas Dennehy saw an opportunity to retaliate. He refused to pay the Trust for more than $5,000 worth of whiskey for which he had contracted on the grounds that the organization was illegal, charged highly inflated costs and averred that it was “impractical and detrimental” to his business to buy liquors elsewhere. The Trust hauled Dennehy into Federal District Court in Chicago and won a judgment. Thomas persisted, appealing the case to the U.S. Court of Appeals. That body found that even if the Trust was an unjust monopoly, other sources of liquor were independent and accessible to Dennehy and ordered him to pay up. He did.
In the end, none of these vagaries of the liquor business proved important compared to the onslaught of Prohibition forces. Neither the politics of the father, Charles, nor the puffery of the son, Thomas, was a sufficient barrier to the moralistic crusade that swept all in the distilled spirits industry before it. By now located on Chicago’s West Randolph Street, Charles Dennehy & Co. was forced to shut its doors after 1918, never to reopen.