This file portion of www.watertownhistory.org website
1892 - 1977
04 30 Harry O’Brien, former Watertown resident and former Jefferson County sheriff as well as one of the all time greats of bowling here, retired today as a deputy United States marshal. O’Brien, who lives in 2344 North 27th Street, Milwaukee, with his wife, the former Louise Koenig of Watertown, has reached the mandatory federal retirement age of 70 years. Mrs. Koenig is a daughter of the late Mr. and Mrs. Hugo Koenig. O’Brien’s career as a law enforcement officer started locally in 1933 when he joined the Jefferson County sheriff’s department as a deputy. WDT
1972 Harry O'Brien was an all time bowling great and in 1972 was elected to the Milwaukee Bowling Hall of Fame. His accomplishments in bowling were many. He was a former Milwaukee and Wisconsin doubles champion, bowled a perfect 300 game and had a three game total of 814.
Harry O'Brien, Bowler, Former Sheriff, Dies
Harry B. O'Brien, 85, 917 Bunker Hill Road, Columbus, Ga., died this morning in Milwaukee. O'Brien was a former well known Watertown resident.
Funeral services are pending at the Schmidt-Bartelt Funeral Home, 550 West Vliet Street, Milwaukee. Burial in Oak Hill Cemetery.
O'Brien was born April 1, 1892 in Chadron, Nebr., son of Mr. and Mrs. James O'Brien. The family moved to Watertown when O'Brien was two years old.
O'Brien's career as a law enforcement officer started locally in 1933 when he joined the Jefferson County Sheriff's Department as a deputy.
His first assignment was that of chief investigator for Attorney H. M. Dakin of Watertown, then district attorney. O'Brien played a vital role in the solution of two Jefferson County murder cases, gaining recognition with the public which later led to his election as sheriff.
The first murder was the slaying in Jefferson of Earl Gentry, former bodyguard for D. C. Stephenson, one-time grand dragon of the Ku Klux Klan in Indiana. Gentry was killed by an itinerant painter named Carl Church. Church was sentenced to life imprisonment. Mrs. Carrie Gill, who operated a Jefferson tavern, was named as co-conspirator, but was acquitted by a jury.
O'Brien was selected Sheriff of Jefferson County in 1936, was re-elected in 1938, serving until 1940.
In October of 1936 while running for the office of sheriff, he helped solve a murder described as "an almost perfect crime." The body of Ferdinand Engelke, a 59-year-old bachelor farmer was found Oct. 4 in his home west of Watertown [cross reference to file on Watertown Police]. The trail led to William Voss, a deaf farm hand. Voss finally confessed to O'Brien that he had clubbed Englelke to death with two pieces of wood after an argument.
Arthur Zimmerman, William Voss [murderer], Harry O'Brien, Harold Dakin, 1936
O'Brien moved to Milwaukee after he was appointed a deputy United States marshal for the eastern district of Wisconsin in 1941.
He was an all time bowling great and in 1972 was elected to the Milwaukee Bowling Hall of Fame. His accomplishments in bowling were many. He was a former Milwaukee and Wisconsin doubles champion, bowled a perfect 300 game and had a three game total of 814.
O'Brien was a 62-year member of the Watertown Lodge No. 666 of the Elks. He was a member of the Bickett Rubber team that participated in the National Elks Bowling Tournament. He led the team to the national championship.
Survivors include four children, Lt. Col. (Ret.) Thomas J. O'Brien, Columbus, Ga.; William H. O'Brien, Costa Mesa, Calif.; Mrs. Nancy Strobel, Highland, Mich., and Mrs. Barbara Yelle, Milwaukee; nine grandchildren and one great-grandchild; one sister, Mrs. Laurine O'Brien Leighte, Milwaukee, and brother-in-law, Gilbert Koenig, who is editor of the Waukesha Freeman.
He was preceded in death by his wife, the former Louise Koenig of Watertown.
History of Watertown, Wisconsin