James Freeman Jr. was born on July 28, 1884 in Mornington Township, the eldest son of James and Cornelia (Nicklin) and raised on the family farm on Lot 4, Concession 10, near the village of Newton.

Early on in his life he showed exceptional business sense. At 17 he was selling farm implements and at 25 he owned and operated a highly prosperous machinery business which served the extensive rural territory. He continued to run his business until 1913, when failing health led to his retirement and his move to the city of Stratford. He didn’t stay retired, he engaged in the contracting and construction business erecting some 30 houses including the one at 197 Albert St. where he and and his third wife Anna are listed as residents of the house in the 1922 tax assessment. James attributed his substantial success to his invariable policy of fair dealing and he prided himself on keeping his promises to the letter.

He married his first wife, Alice Generva Thorpe, born August 5, 1892,  on June 19, 1912 and they welcomed a daughter Charlotte May the following year on June 4. Alice would die on August 15, 1914 at the age of 22 from consumption.
 
His second wife, Eleanor “Ella” Lavina Squire was born on June 10, 1893 in Mornington Township and they married on September 29, 1915. A son William  James was born on August 4, 1916 followed by another son Floyd Squire in November 1918. Eleanor died on November 7,1918 from complications during his birth and pneumonia.

Anne Heinbuck born on September 29, 1903, became James’s third wife on May 10, 1922.  In James’s obituary there is mention of another  daughter, Alice Eleanor, living at home.  As of 1962 she was still listed as a spinster living at 25 Douglas St.

James was a long faithful member of St. John’s United Church. He was on the building committee when it was built. He joined the I.O.O.F. as a member of Millbank Lodge and continued to be a member for 34 years.

He died on September 21, 1939 after a lingering illness of which confined him to his bed for 6 years while living at 25 Douglas St. in Stratford. He is buried in Avondale cemetery.