Last Saturday, the following ad showed up in the Vintage Ads LJ community (holy shit yes, I still sometimes use Livejournal) and I immediately became enamored with it.

1908 ad

I am really into old ads and Chicago history, and the ad copy filled me with joy. I loved the idea of a female PI working the South Side of Chicago during the Progressive Era. My mind almost immediately started concocting stories and cases for her (historical fanfic? Is that a thing?). Cheating husbands, missing daughters, crooked alderman, maybe even a murder in the Stockyards. I was sure she had an affair with Upton Sinclair and her nemesis must have been H.H. Holmes.

I resolved to find out as much about her as I could. I never would have guessed that I would find so much and that she completely lived up to my expectations. So here is a timeline and documentation of everything I could find out about her (or at least as much as I could while spending no money and "researching" from the comfort of my couch). I HIGHLY recommend you click the links and read the articles. They're amazing.

I'm glad I can share this with the rest of the internet, feel free to hit me up via email or twitter with any comments, questions, or extra information you might have.

1868 -
Cora M. Strayer is the oldest of 4 children born to farmers Frank and Mahala Strayer in Elkhart, Indiana.
1885 -
At age 17, Cora marries a man named George W. Murray in Elkhart. I can't find anything else about this guy.
1885-1898 -
Sometime in here George dies. The 1890 census would be really helpful figuring out if he was still alive and what their location was that year, but almost all of the data was destroyed in a fire in 1921. In the 1910 census Cora lists herself as widowed, and as having given birth to two children, both of whom were no longer living. A "George Murry" who's in the right age range, did die in 1894 in Pierceton, IN, which is only 40 miles from Elkhart.
1898 -
Miss Cora Strayer is living at 3819 Wabash in Chicago. She lists her job as "Clerk."
1902 -
The first ad for her detective agency appears! It's at 5453 W Lake - a 4-room apartment with $18 a month rent. The apartment is above a tavern that was consistently being raided by the cops for it's illegal poker room and bookmaking operations.
Aug 1903 -
Cora is profiled in the Chicago Tribune under the matter-of-fact headline "Woman Directs A Detective Bureau". In it she claims that she originally studied law and practiced as an attorney for several years.
1905 -
The first big ad in the Chicago city directory, complete with photo! Cora has moved to 3104 Cottage Grove, and a George S. Holben is named as the "Supt. of the Criminal Dept." In 1903 Holben was involved in a robbery where his landlady accused him of drugging her and stealing $750 worth of diamonds. Several weeks later, the diamonds were still missing, but Holben was not prosecuted. I don't know if Holben was working for Cora yet when this all went down.
Apr 12, 1906 -
Mahala Strayer dies at age 60. Her address is on Cottage Grove not far from Cora, so I assume her and Frank moved to Chicago at some point.
1907 -
Cora is hired by a Mrs. Campbell who believes that a Mrs. Harris is writing fake letters in order to make it look like she is having an affair with Dr. Harris and so she may blackmail her. Cora takes Mrs. Harris on a trip to Milwaukee, gets her drunk on $150 of fine wines, and steals the letters when she is passed out. Turns out Mrs. Campbell and Dr. Harris actually were having an affair and he performed an abortion on her. Mr. Campbell eventually killed Dr. Harris.
1905-1912 -
During this time ads for Miss Cora M. Strayer's Private Detective Agency appear consistently in both the Chicago Tribune and the "Blue Pages." I'm guessing business is going pretty well.
July 1908 -
George Holben has lost his diamond lapel button, and he lists his address as the same as Cora's.
1908 -
The ad with the awesome copy. "Ladies, when in need of legal or confidential advice, why not confer with one of your own sex?" She's found a niche! Also, I'm calling bullshit on this "Est in 1890" claim. I can't find any record of the agency before 1902, and going from a 16 year old girl married in Elkhart, to a 21 year old single attorney/detective in Chicago seems like a pretty whirlwind ride for a woman of the time.
1909 -
"Business Women Who Have Made a Success of Bossing Men" - Cora is one of the subjects of a full-page article in the Sunday Tribune about female business owners. In it we learn that Holben was her first employee and that she is moving her office. The article also features a photograph of her and Holben in the office.
1910 -
In the 1910 census, Cora lists herself as widowed, but living with George Holben at 2838 Indiana Ave, she is 41 and he is 34. Also in the household is Hanna Newberg, a 29 year old Swedish immigrant. Cora lists her profession as "Detective" and George is a "Journalist".
Dec 5, 1910 -
George Holben is shot and killed by Stephen Ayers, a 33 year old disgruntled ex-employee of the agency. Ayers claims that he met Cora in Seattle over the summer and that they traveled along the west coast with each other. He says that Cora invited him to Chicago with with promises of a job and marriage, but that she was being held hostage by Holben. Cora denies any love affair and says that she ordered Ayers fired due to unreliability. The murder even gets coverage in Los Angeles. Ayers is later sentenced to 15 years, and in 1913 he escapes from prison, but was caught two days later.
1912 -
George Holben is no longer listed on the ads.
1911-1912 -
At some point here Cora marries a man named Robert L. Fortune. He works in real estate. Cora is 43 and Fortune is 24, continuing her penchant for younger men.
Feb 19, 1913 -
Robert Fortune dies. According to his death certificate he had oral cancer ("sarcoma of the fauces and palate") and a contributing factor was "exhaustion following a number of operations for removal of growths." I'm guessing all these treatments led to Cora's later bankruptcy. (Thanks Christopher Wilde for finding the cert.!)
Oct 1913 -
Cora files for bankruptcy and is over $9000 in debt. I just realized that all the men connected to her ended up dead before the age of 40, how sad.
1914 -
"Colonel" Cora Strayer forms the First Volunteer Women's Calvary Regiment to take up arms and join the fight in the Border War with Mexico. The killer quote from her:
"Do you want to wait until all the men are killed to do your duty, sisters? A woman that would stand and let a man do all the fighting and suffering for his country is not a soldier. She belongs in the effete ranks of those who hurry abroad when the trouble starts. Pooh! She is not even worthy of the ballot."
Apr 1914 -
The regiment has 100 women.
May 1914 -
200 women.
1918 -
Cora is hired by the friends of a Mrs. Russell, who think her husband is having an affair. She is joined on a stakeout by police, who want to bring up Mr. Russell and his mistress on morals charges. The situation culminates in a car chase up Lake Shore Drive with Cora in pursuit behind the wheel of her black sedan. The ensuing case receives big coverage. Also, check out the awesome Wurlitzer ad on that page. They're "sanitary" records!
1920 -
In the 1920 census Cora is still living at 2838 Indiana, but her retired father Frank has now moved in with her.
May 1923 -
The office has moved to 4933 S. Michigan Ave.
Apr 13, 1927 -
Frank Strayer dies in Chicago.
1930 -
On her 1930 census form Cora lists herself as "Cora Fortune". She says she is 61 years old, a widow, and can read and write. She pays $40 a month in rent. She is still working, owns her own business, and declares her profession to be "Investigator".
Dec 1930 -
This is the last ad I can find for the agency. The office is now at 5834 S Wentworth. (Thanks to Brian Wolf for hooking me up with access to old Tribunes).
Dec 19, 1932 -
Cora May Strayer Fortune dies in Chicago. She was 64.