On Thanksgiving Day of 1833 he founded the "Chicago Democrat" (1833-1861) newspaper. He lived on State Street at the corner of the alley between Madison and Washington Streets and usually walked through the alley for a short-cut to his print shop.
|The south west corner of Madison and Dearborn|
showing "Newspaper Alley," Chicago. 1853.
The Chicago Times (1854 to 1895) was the first newspaper user of the alley. It was started on the site of the old University Club. Newsboys entered the basement through a stairway off the alley and there received their papers to sell.
|Newspaper Alley... the first Tribune building would be erected here in 1869.|
Other famous users of the alley, all of whom have gone out of business or moved away, were the Chicago Board of Trade ; the Chicago Open Board of Trade ; George Clark's concert hall; "Appetite Bill's" saloon in which Jere Dunn killed Jimmy Elliott ; the Round Bar in which "Doc" Haggerty was killed by "Bad Jimmy" Connorton ; the Whitechapel Club ; William "Silver Bill" Riley's Poolroom; John Condon's , Pat Sheedy's, and "Si" James' gambling houses; Bill Shakel's "clock."; "Bathhouse John's silver dollar saloon (1895-1914) ; Billy Boyle's Chop House ; Harry Varnell's Big Faro Game ; and Jim McGarry's place, where Finley Peter Dunne got the inspiration for his "Mr. Dooley. "
On May 7, 1918, the passing of the Chicago Herald as an individual publication and the subsequent address 30 Newspaper Alley was the occasion for a tribute to the few hundred yards of famous brick and stone.
NEWSPAPER ALLEY GOES DARK FOR THE FIRST TIME.
Lights went out for the first time in a half century on May 10, 1918 in the famous old "Newspaper Alley." Its passing came with the sale of the Herald, and the ending of its night life. Between midnight and 5 o'clock A.M. the alley in former days was full of bustle and activity. Wagons and auto trucks were coming and going. At times the alley was choked with traffic.
 Calhoun Place, (20 North - 1 to 400 West) named after John C. Calhoun editor of the Chicago Democrat the city’s first paper. He died in Chicago on 20 Feb 1859 at the age of 51 years old. Nick names but nothing official: Newspaper Alley, Whitechapel Alley, Gamblers Alley, and Newsboy’s Alley.
 The completion of the Illinois & Michigan Canal in the fall of 1847 and its opening in the spring of 1848 inspired the formation of the Chicago Board of Trade, the city's first voluntary association of businessmen. The Board of Trade reorganized in 1850 to conform to a law governing boards of trade passed by the Illinois General Assembly in 1849.
The city's merchants adopted their procedures to handle grain in bulk, not in bags, as traditionally had been the case. The first small shipment of grain in bulk had occurred in 1839. Chicago's grain traders gained national recognition as a reliable and competitively priced source of grain during the 1850s.
The Board of Trade enhanced its role in the grain trade by implementing regulations for grading grain. The state legislature recognized its regulations by granting it a special charter in 1859. The special charter gave the board the power to impose rules and regulations for handling of grain and to arbitrate disputes between commodity merchants.
 The Chicago Open Board of Trade was organized in 1880 and has survived as the Mid-America Commodity Exchange and is a subsidiary of the Chicago Board of Trade. A butter and egg exchange that traces its roots to the post–Civil War era was reorganized in 1919 as the Chicago Mercantile Exchange.
 How I Killed Three Men, Chicago Daily Tribune, July 1, 1890.
 He murdered "Doc" Haggerty, Chicago Tribune, February 17, 1891
 The Whitechapel Club was started in 1889 by a small group of newspapermen in Chicago, Illinois. The club was named after the area in London where Jack the Ripper murdered his victims. It only lasted five years, ending in 1894. While the core of the club members were newspapermen, the club members included artists, musicians, physicians and lawyers. Some of the well known members of the club included Brand Whitlock, George Ade, and Finley Peter Dunne.
Inside, the Whitechapel Club looked more like a trophy room for murderers rather than club house. Walls were decorated with Indian blankets soaked with blood, nooses, knives that had been used to kill, and pictures of pirates who had been beheaded. Skulls, used to drink red fruit juice, lay everywhere, and a full-size model of their "President," Jack the Ripper, was placed in a corner. Pipes, cigars, and alcohol would be easily found in any room as well.
Meetings at the Whitechapel Club would usually start around midnight. Because Jack the Ripper was never in attendance, meetings would be chaired by the Vice-President. Club meetings were very private, although guests very occasionally were brought. During meetings, people would tell stories, jokes, poems, or monologues. It was customary to yell insults at whoever rose to speak to the club. Throughout the meetings, members would drink heavily.
In later years of the club’s existence, membership became very coveted. In order to become a member a candidate had to go through an initiation. First, only two members of any profession could belong to the club at any time. The new member, known as a probationary member, would go to club meetings for one month. At any time during that month, another member could reject him from becoming a member. If the first month was survived a club-wide vote would be made whether to keep or reject the man. If one vote was a “No” he would not get membership to the club.
 The story of Bathhouse John. Chicago Tribune, May 24, 1953
 Billy Boyle's famous "chophouse in the alley," at 5 Calhoun Place, Chicago, known widely since 1875 among Bohemians of Chicago and those by other cities visiting Chicago, was closed on March 20, 1895 by its creditors. High rent, many "tabs," and a declining business have put an end to the noted "all night" resort.
 Faro, Pharaoh, or Farobank is a late 17th-century French gambling card game. It is descended from basset, and belongs to the Lansquenet (card game) and Monte Bank family of games due to the use of a banker and several players. Winning or losing occurs when cards turned up by the banker match those already exposed. It is not a direct relative of poker, but faro was often just as popular, due to its fast action, easy-to-learn rules, and better odds than most games of chance. The game of faro is played with only one deck of cards and admits any number of players.
 Finley Peter Dunne (1867-1936) was an American humorist and writer from Chicago. In 1898 Dunne published “Mr. Dooley in Peace and in War,” a collection of his nationally syndicated Mr. Dooley sketches. The first Dooley articles appeared when Dunne was chief editorial writer for the Chicago Post, and for a number of years he wrote the pieces without a byline or initials. They were paid for at the rate of $10 each above his newspaper pay.
A contemporary wrote of his Mr. Dooley sketches that "there was no reaching for brilliancy, no attempt at polish. The purpose was simply to amuse. But it was this very ease and informality of the articles that caught the popular fancy. The spontaneity was so genuine; the timeliness was so obvious." In 1898, he wrote a Dooley piece that celebrated the victory of Commodore George Dewey over the Spanish fleet in Manila Bay—and this piece attracted national attention. Within a short time, weekly Dooley essays were syndicated across the country.
In 1899, under the title Mr Dooley in Peace and War, a collection of the pieces was brought out in book form, received rave reviews from the critics, and was on the best seller list for a year.