In looking back at Chuck's image with the Colonial men and their Old Underoof, perhaps there's some symbolism here. The clovers are perhaps representative of Ireland itself, Charles Dennehy's land of birth. They form a roof for the brand name, Old Underoof, to be under. The Colonialists toast in the direction of Ireland (the clovers) while one carries a bottle of the whiskey. The colonists are in green, perhaps identifying them as Irish-Americans. Perhaps this drawing/ad is saying that just as the Colonial Americans freed themselves from the British, so too shall Ireland and the Irish.
While very much a blend, honestly admitted on the bottle label, it seems Charles Dennehy wanted to present his whiskey as a cut above. And the advertising journals point to Charles Dennehy & Co as being innovative (certainly for a smaller brand).
If for the most part he didn't make his own whiskey, why emphasize in the one ad the use of heavy char and heated warehouses? Was he re-aging the whiskey he bought? I don't know if this was a common practice for the liquor wholesalers of the day.
Just to add a little bit of spice here, it appears that the Dennehy company was involved in a legal battle with the Distilling & Cattle Feeding Company in 1897-1898. The appeal of the case can be found at OpenJurist
. The case involved questions involving rebate vouchers given to Dennehy from the D&C-F Co, which was declared an illegal monopoly. Some of the names involved, which may lead to other distillers, wholesalers, and their businesses are listed below. Dennehy claimed to be owed $5238 in rebates at 7¢ per proof gallon. This means he'd purchased nearly 75000 proof gallons; if the whiskey was barrelled at proof, that would be about 1400 barrels. So about 300,000 quarts.
Apparently, D&C-F Co was an illegal trust, acting as a monopoly, controlling 85% of the liquors available in the country at this time (according to the court documents).
J. B. Greenhut, President, Distilling & Cattle-Feeding Company
German-American National Bank of Preoria, Ill. (was to pay the vouchers)
Stein Brothers (another claimant for $3604), Moses Salomon, the assignee of these vouchers, an attorney
United States Distilling Company (mentioned as receiving the vouchers, endorsed by Dennehy)
G. E. Jones (an officer of USDCo?)
The offices of Charles Dennehy & Co, distiller and importer of fine liquors, are given as 39 South Water Street, Chicago, in the 1890 edition of St. Luke's Free Hospital Annual Report. (Various companies advertised.)
Now, we come to the Congressional serial set By United States. Government Printing Office
where we have a case decided Jan 5, 1909, Charles Dennehy & Co v. Robertson, Sanderson & Co. Limited. Apparently Dennehy tried to trademark the term "Mountain Dew" in 1905, but was declined as the term was seen as being in common use as referring to whisky. As also was challenged by a Scottish distiller (the Robertson, Sanderson & Co, Ltd).