1911 is late in our timeline. By 1910 , the oldest three children are off on their own and the two youngest daughters are already in the orphanage. But who knows how long May Gaines was on the scene or what her role was in disrupting the family.
On the Moses' death certificate filed from St. Vincent's Institution, he is listed as Married, but spouse is "unknown."
As for the poisoning, see the Tidbit below.
Other women who names come up in association with Moses are Maggie's sister Delia and Moses' sister-in-law Bridget.
The story has it that when Maggie Keville Flanagan died in 1903, her sister, the widow Delia Walsh came to town with her two daughters to help out. In 1903, her daughter Mary was 9 and Margaret was 7, the ages of Maggie's Joe and Moses. This didn't work out at all. The implication was that she and Maggie's husband Moses didn't get along.
Luckily, she hadn't sold her big house in Chicago and moved back there in time to be counted in the 1910 Census.
Rose Park  was wondering why she didn't take the youngest girls back to Chicago with her - she clearly had the room and was easily moved to kindness. Perhaps she offered. Perhaps Moses the proud and stubborn Irishman refused her offer. Perhaps big sisters Nellie and Kitty protested. Perhaps Moses simply loved the little darlings too much.
Since Delia ran a boarding house and came to St. Louis apparently prepared to stay, I suspect she was a take-charge kind of woman. Maybe it was she who investigated the option of Guardian Angel Industrial School for the little girls as a humanitarian alternative to a motherless household.
Around the corner from Delia Walsh on 48th Place in Chicago was Bridget Mehan Flanagan. Bridget was married to Moses' brother Jerry and, although he was a laborer in the stock yards, they owned their own home. Some time between the 1900 and 1910 Census, Jerry died.
A family story goes that Bridget moved to St. Louis and married Moses. She must have brought her two young sons, just as Delia had brought her daughters. Apparently, this arrangement was no more successful than Delia's. If we have our facts straight, she was back to Chicago by 1910.
in 1911, he married the 42-year-old May Gaines, in Clayton MO. 
Conspiracy corner. My cousin Barbara came up with this -- apparently told to her mother by Kitty Mom (Moses' 2nd daughter, our grandmother). When Moses died in 1920 (remember he was in a mental hospital then), Kitty Mom got an anonymous letter from someone urging her to exhume his body. The writer claimed Moses had probably been poisoned by his wife, since she had poisoned her first husband. A whacko? Who knows. We've grown to expect the unexpected with this family.
Perhaps totally unrelated... a month after Moses Flanagan died, a "May Gaines" married Pride L. Jones in Chicago. While Moses died of an infectious brain syndrome, the estranged May Gaines might have been waiting for him to be out of the way so she could get on with her life. I found no evidence of any marriages prior to Moses.
3.31.05 (rev.3/30/08, 5/17/2016)
 Missouri Marriage Records, .
 distant cousin and fellow family historian
 Census data
b. Dec 1865, Ireland. Married to John Walsh, 2 Jun 1887.
Daughters: Mary E, b. Jun 1894, Illinois; Margaret, b. 1896, Illinois.
Living on 4808 Union Av, Chicago, in a home she owned. With daughters and 5 boarders, including Pat Keville (b. Mar 1873 Ireland, to US in 1890) and Chas. Keville (b. May 1878 Ireland, to US in 1897). The other boarders were John Egan, Barney Hand, and Chas. Smith.
Same address, with daughters and 3 boarders, incl. Charles Keville. The others were Mulhoney Scanlan and Thomas Durkin.
b. Feb 1861, Ireland. Immigrated 1880.
Married to Jeremiah (Jerry) Flanagan, b. 1860 Ireland. Immigrated 1880. In 1910 worked as a laborer in the Chicago stock yards.
Sons: Timothy Joseph, b. 1 Aug 1892 Illinois; James Jerome, b. 2 Oct 1884 Illinois.
Owned own home with Jerry on W. 48th Place. Boarders: niece Hannah Hayes (b. Feb 1887 Ireland, to U.S. in 1899, working as a domestic) and nephew John Flanagan (b. Apr 1878 Ireland, to US in 1898, working in the stock yards)
Widowed, living with 2 sons and 2 boarders (record almost illegible). 4757 Union Av.
5 Jun 1917 Draft Registration
Tim (tall, slender, blue eyes, dark hair), working as Yard Brakeman for Pittsburgh Fort Wayne Chicago Railroad, 55th. Living at 4720 Union Av.
James (med, slender, lt blue, lt brown). Same workplace and address as Tim.
Still listing herself as "widowed" living in her own home on 944 51st Place (Chicago), still with her two sons, now grown. Tim working as a clerk with Morris Packing and James working as a switchman with the Rockford Railway
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