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Harry was born in Dublin, Ireland on Sunday, November 12, 1876 to Joseph and Catherine (nee Kearns) O'Keefe. He was baptized on November 20, 1876 in the church of SS. Michael & John in South Dublin with the name Michael after his paternal grandfather, Michael O'Keeffe. Margaret O'Keefe was listed as his sponsor. It was in the same church and by the same priest, Rev. John O'Hanlon, who married his parents. From the very earliest times Harry Michael O'Keefe was his formal name but he always went by Harry. His sister, Elizabeth, was 2 ½ years old. In April 1883, when he was 6 years old, the four of them immigrated to the United States and settled in Cleveland, Ohio. On October 25, 1892, he was naturalized thru his father because he was a minor (15 years old). Harry was listed in the City Directory as an ironworker before enlisting in the U. S. Calvary. Apparently, during most of his adult life he dropped the "O" and went by Harry M. Keefe.

Harry enlisted on September 19, 1898 when he was almost 22 years old and served until January 25, 1899 in "F" Troop, 2nd U.S. Calvary. After basic training and because the Spanish American war ended December 10, 1998, he was discharged in Huntsville, Alabama and returned to Cleveland. However, shortly after The Philippine Insurrection began in February 1999 he re-enlisted in Cleveland on March 13, 1899 in "M' Troop, 4th U.S. Calvary. His enlistment papers show his height as 5' 6½" and 5' 7¼" respectively with brown eyes on one document and blue eyes on the other. It seems they could agree on brown hair and fair complexion. It took six days to travel by train from Cleveland to the Presidio in San Francisco. On June 28, 1899, Harry shipped out on the troop transport "Valencia" which made a short stop in Honolulu on the way to the Philippines. The voyage took 32 days. Harry kept a journal almost daily from March 13, 1899 to May 12, 1900 and again from February 22 to March 13 in 1901. He chronicled what it was like serving during the Philippine Insurrection, which many still referred to as the Spanish-American War in the Philippines. It is very interesting reading. A copy of his journal has been transcribed and is available in computer readable form. His handwriting showed the artist in him and the journal is in excellent shape considering the severe conditions he endured during the war. He contracted malaria, suffered malnutrition and food poisoning while he served in the Philippines. This could explain some of the gaps in his journal. He also served in "G" Troop, 15th U.S. Calvary and after attaining the rank of sergeant was finally discharged on March 18, 1902 in California and then returned to Cleveland.

A little over eighteen months later he married Frances Margaret Seitz on Wednesday, November 11, 1903 in St. Francis Church, Cleveland, Ohio. He was 27 years old. She was 21. Harry and Frances moved in with his parents for about a year when their first child, Gertrude Catherine O'Keefe was born October 19, 1904 and again when Edward Joseph O'Keefe arrived May 11, 1907. Harry's occupation was listed as machinist from 1903 through 1916 except for the year 1907 when he was listed as a fireman. In 1910 they moved to 1460 East 93rd Street, which would be their home until 1926. Bernice Frances O'Keefe was born December 23, 1917. When Bernice was born Frances was 35 and Harry was 41. Gert was 13 and Ed 10 years old. From 1917 until 1922 Harry was a foreman (of machinists).

On September 12, 1918, Harry registered for the draft as required, even though he was two months shy of his 42nd birthday. On August 16, 1922, at the age of 45 Harry started working for the U. S. Government's Veteran's Bureau (later called Veteran's Administration) serving in Dayton, Columbus, Lexington and Toledo before finally being assigned to the Cleveland office. Harry and Frances bought a home that had been built in 1927 at 1251 Irene Road, Lyndhurst Village in what was called the Mayfield Highlands.

The only story Harry's son, Edward, ever told his children about their grandfather was about the time when Harry had to go to a small town in Kentucky or Tennessee and a local who operated a moonshine still fired a rifle at him from across the street, hitting a mail box that he was standing beside. He returned fire with a small .25 caliber automatic pistol that he carried. Apparently neither was hit and it could have well been a warning shot because he was a "government man" even though he had nothing to do with liquor control. His grandson, Richard, now has that pistol that maybe saved Harry's life.

Harry was also an artist. He produced many pen and ink sketches, mostly of western themes. He also painted several pictures, some of which are still displayed in his granddaughter's home.

Harry began suffering from cardiac disease and coronary thrombosis in 1933. Harry suffered a heart attack at his home at 1251 Irene Road, Lyndhurst, Ohio on October 8, 1937. He was taken to the U.S. Marine Hospital in Cleveland where he died the next morning on October 9, 1937 at the age of 60. The wake was held at the family home. After a Requiem Mass at St. Gregory the Great Catholic Church, he was buried at Calvary Cemetary section 12 lot 183. Harry and Frances were married 33 years. His wife was buried at his side some 43 years later.

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