Regarding the Old Underoff brand, just some things I found doing a google search.
There's an ad in the Spokesman-Review, Nov 19, 1903 for Old Underoof, produced by Chas. Dennehy & Co, Chicago. The ad says that it is "Pure. Old. Delicious."http://news.google.com/newspapers?nid=1 ... 55,2282141
The same ad appears in the Spokane Daily Chronicle of Jan 13, 1904.http://news.google.com/newspapers?nid=1 ... 662,766686
It is also listed in the American Food Journal, Volume 2, (1907) where is is claimed that it is "free of fusel oil and tanic acid"http://books.google.com/books?id=6HxNAA ... of&f=false
The The Inland and American printer and lithographer, Volume 22, (1899) mentions that the advertising for Old Underoof whiskey is getting attention by using current events (such as the arrival of the new Japanese Minister Jutaro Kumora in Chicago).http://books.google.com/books?id=g_ooAA ... of&f=false
The Library of advertising, Volume 4 (1911), Axel Petrus Johnson, mentions Wilson's
"Old Underoof". They're mentioning that metal lithography is very common with big national brands such as Coca-Cola, the brewer's Pabst, and a dozen distillers products such as the Old Underoof.http://books.google.com/books?id=OTZOAA ... 8Q6AEwAjgU
In a Daily racing Form ad from June 22, 1900 we have this very interesting page where it is said "matured in heavily charred oak barrels in warm storage".http://kdl.kyvl.org/cgi/t/text/pageview ... et&seq=3_2
From A directory of names, pennant numbers, and addresses of all members of the ... By Ship Masters' Association of the Great Lakes (1904) we have the address given of the Chas. Dennehy & Company as 216 and 218 Randolph Street, Chicago. (With long distance telephone main 2077).http://books.google.com/books?id=CC7YHi ... of&f=false
And please do not forget that "it is not wise economy to save "the slight difference in cost between Old Underoof rye and other whiskies" when you get such superior quality in Old Underoof Rye. As listed in The Chicago medical recorder, Volume 26, Part 1 (1904)http://books.google.com/books?id=k0NYAA ... of&f=false
The book The great revolution: a history of the rise and progress of the People's Party (1874) By M. L. Ahern gives a biography of Mr. Dennehy. It states he is a member of the firm Weadly, Dennehy & Cleary, a wholesale liquor house. And a leading member of the People's Party.
And in the book History of Chicago, Volume 3, (1886) there is an extensive section of the brewing and distilling trades, and a brief biography is given. Born in Ireland, came to the US, apparently was in the grocery business in Alabama before moving to Chicago.http://books.google.com/books?id=THd5AA ... &q&f=false
Hopefully I haven't duplicated something that the real historians here have already posted somewhere.