I have applied for the marriage certificate for James to Mary Heslop in March quarter of 1890, so it will be interesting to see what that says about his marriage status.
James's marriage to Anne Eliza Millsop/Montgomery was either annulled or they got divorced or both became Bigamists!
Eliza Millsop
mentioned in the record of Isaac Winter and Eliza Millsop
Name: Isaac Winter
Event Type: Marriage
Event Date: 13 Oct 1888
Event Place: Mahoning, Ohio, United States
Spouse's Name: Eliza Millsop
Reference ID: 192 , GS Film Number: 906675 , Digital Folder Number: 004017181 , Image Number: 00458
We have already established that Eliza's mother Dorcas Montgomery along with Eliza's son John Montgomery Millsop were living in Mahoning, Ohio in 1900.
But now I've found Eliza with Isaac Winter and an infant son in the 1910 census.
Isaac Winter
United States Census, 1910
Name: Isaac Winter
Event Type: Census
Event Year: 1910
Event Place: Youngstown Ward 2, Mahoning, Ohio, United States
Gender: Male
Age: 52
Marital Status: Married
Race: White
Race (Original): White
Relationship to Head of Household: Head
Relationship to Head of Household (Original): Head
Birth Year (Estimated): 1858
Birthplace: England
Immigration Year: 1886
Father's Birthplace: England
Mother's Birthplace: England
Household Role Gender Age Birthplace
Isaac Winter Head M 52 England
Anna E Winter
Wife F 54 Scotland
Esther Winter
Daughter F 21 Ohio
Mary Winter
Daughter F 14 Ohio
Robt J Winter
Son M 1 Ohio
District: 115 , Sheet Number and Letter: 1A , Household ID: 4 , Affiliate Name: The U.S. National Archives and Records Administration (NARA) , Affiliate Publication Number: M1283 , GS Film number: 1375225 , Digital Folder Number: 004449945 , Image Number: 00368
Eliza gives her age as 54 and born in Scotland, which is close enough to her birth on 24 September 1855 in Bothwell.