Charles was a lawyer who became influential in Minnesota Territory after moving there in 1853 from New York City.  In 1859 he married his first cousin, Isabella Dinsmore.  The wedding ceremony was held in the Dinsmore parlor and was probably followed by a large dinner for family and friends.  They had two daughters: Martha Macomb (‘Patty’) in 1861 and Sarah Gibson (‘Sally’) in 1867.  In 1862, during the Dakota War, Flandrau enlisted to defend settlers at New Ulm as part of the Union Army.  His leadership earned him an appointment to head the defense of southwest Minnesota as a colonel. His career included serving on the Minnesota Territorial Council, in the Minnesota Constitutional Convention, and on the Minnesota territorial and state supreme courts.  

In 1866, his wife, Isabella, died, having never fully recovered from childbirth six months before.  She was buried in Kentucky and Patty and Sally were raised in Kentucky by their Aunt Julia.   Charles went on to remarry Rebecca Blair Riddle, a widow with one son, John Wallace Riddle, Jr.,  and together they had two more children, Charles Macomb and William Blair McClure.  In 1870, he moved to St. Paul, where he practiced law until the 1890s.

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