January 14, 1919 (Greenwich, CT) – February 1, 1943; 24 years old; unmarried
Last local address: Chestnut Hill Road, Norwalk
Enlisted: August 26, 1941
Service number: 11033041
13TH ARMY AIR FORCE, 11TH BOMBARDMENT GROUP (HEAVY), 42ND BOMBARDMENT SQUADRON
Awarded the Distinguished Flying Cross, Air Medal (twice), and Purple Heart Medal
On February 1, 1943 Sgt Olmstead was the assistant radio operator and left waist gunner on B-17E #41-9151, assigned to the 13th Army Air Force, 11th Bombardment Group, 42nd Bombardment Squadron. They were flying from Henderson Field on Guadalcanal as part of a nine-plane mission to bomb Japanese shipping. After successfully bombing a ship in Tonolei Harbor Bougainville they turned east towards Choiseul Island when they came under heavy attack from fifteen to twenty-five Zero fighter planes. Olmstead’s plane was shot down and the crew declared missing in action. On January 11, 1946 the Army officially declared them dead.
Pilot Major Earl O. Hall, Jr., O-325099, C. O. of the 42nd BS (MIA / KIA) Crawford, TX
Co-Pilot 1st Lt Joaquin Castro, O-428914 (MIA / KIA) Mission, TX
Navigator 2nd Lt Frank N. Stern, Jr., O-438256 (MIA / KIA) Chicago, IL
Engineer TSgt Paul Adler, 6147915 (MIA / KIA) Cambridge, MA
Bombardier SSgt James Y. Bales, 15058894 (MIA / KIA) Crawfordville, IN
Radio SSgt James C. Stephens, Jr., 6953552 (MIA / KIA) Pania, CO
Asst. Engineer SSgt Francis S. Banasiak, 11020224 (MIA / KIA) Holyoke, MA
Asst Radio Sgt Jesse N. Olmstead, 11033041 (MIA / KIA) Norwalk, CT
Gunner Sgt Martin T. Grady, 6980875 (MIA / KIA) New York, NY
From The Norwalk Hour June 12, 1943
NORWALK MOTHER TO GET MEDALS FOR ‘MISSING’ SON
Presentation To Mrs. Mary E. Olmstead on Sunday At 2:30 At Community Baptist Church
A proud but sorrowing Norwalk mother will receive on Sunday at 2:30 P.M. at the Community Baptist Curch, the medals of valor awarded by the War Department to her son, one of three in the armed service. She is Mrs. Mary E. Olmstead, now of 23 Reservoir Avenue but until a week ago, of Chestnut Hill Road. Her son, missing in action in the South Pacific since February 1, is Sergeant Jesse Olmstead, 24 on January 14th, who attended Franklin Junior High School and Norwalk High School. The presentations will be made at the Community Baptist Church by Colonel Urband who will come here from Groton. The awards to be presented to Mrs. Olmstead are the Distinguished Flying Cross, two Air Medals, and the Oak Leaf Cluster, one of these for bringing down a four motored Jap bomber on August 26. Jesse’s last flight, apparently, was on January 29 his mother thinks, because he wrote to her on January 28 and the dispatches from the South Pacific told her of a big air battle the net day and as she received notice on February 11 that he was missing, she figures that he must have been in that January 29 fight. She did not receive his letter, a cheerful missive as usual, until a day after she was notified that he was missing in action. There were eight others in his plane, all now missing. Jesse entered the service on August 26, 1941. He had been studying and working at radio. He liked it and had a room set up in his Chestnut Hill Road home. He had everything in it, his mother said, and she was heartbroken when she had to dismantle it to move to Reservoir Avenue about a week ago. Jesse was sent immediately to radio school, then to another, more advanced, until he was ready for flying service. “My ‘Tiny’ was a fine boy,” said Mrs. Olmstead at her home yesterday. “He always made light of what he was doing in the big fights in the South Pacific, but I could tell from his letters an watching the reports of the battles from Washington that he had been in some big fights. He had been in that area since May 1942. I feel mighty proud of him and the recognition he has received from his superiors. I wish he were here to get them himself and I hope that some day he will come back so that I can hand him his medals for him to wear. He may have been saved. He had a good head on his shoulders and if there was any way of coming through, he’s make it. “I have two other boys in the service. LeRoy, 22, we call him ‘Laddie’, is in the air service too, a ground mechanic. He entered on July 8, 1942. Then I have Robert, ‘Robbie’, who will be 27 on June 17th. He’s a gunner on a tank. He entered December 17, 1492. “My boy ‘Laddie’ is now home on leave, 15 days. He goes back next Tuesday so he will be at the church on Sunday when I receive the medals. So will all of my family. The Rev Mr. Brainard Brown and others will be at the church. I was told by Colonel Anderson who phoned from Windsor Locks, that the presentation would be made at any place I selected and I picked the Community Baptist Church because my boy Jesse, sang in the choir there for three years. Some of my other children sang there too. He liked the church and i do. “Of course I’m proud of his medals but then I’d like to have my boy here to receive them himself. I’d like to pin them on his breast. He’s done a good service for his country.”
From The Norwalk Hour June 12, 1943
Friends and relatives attended the special service at the Community Baptist Church yesterday afternoon, when Mrs. Mary E. Olmstead of 23 Reservoir Avenue was presented with two medal from Lieutenant Colonel Edward M. Urband of Groton. The medals, honoring her son, Sergeant Jesse Olmstead, missing in action in the South Pacific since February 1, were the Air Medal and the Oak Leaf Cluster for her son’s work in the Pacific battle area. Colonel Urband made the presentation from the platform of the church and spoke briefly on the accomplishments of Sgt. Olmstead. Mrs. Olmstead has also received two other medals honoring her son. During the program, the congregation, numbering about 100, sang “America” and a church hymn. Thomas Hyde played the violin and Boris Lang, the organ. Rev Brainard Brown said the prayer for the occasion and presented Colonel Urband to those present. Sergeant Olmstead for five years, never missed a day in Sunday School at the Baptist Church. Mrs. Olmstead was accompanied at the ceremony by a son, LeRoy, who is with the U.S. Air Corps. She has another son, Robert, who is a gunner on a tank. The citations follow:
January 10, 1943
Jesse N. Olmstead, PFC, U.S. Air Force, for meritorious achievement in air action against the enemy on August 26, 1942, in the Solomon Islands area. Private Olmstead, as a member of heavy bombardment airplanes on a search mission, participated in an attack upon a Japanese four engine flying boat, sighted and engaged, at a point 50 miles north west of Giza Island. Enemy craft turned away but was overtaken and again engaged for approximately 15 minutes and finally shot down by Private Olmstead and other members of the crew. Airplane attacked by enemy fighter which made one ass, securing two hits on the left wing, then pursued out of gun range for approximately 50 miles before turning away.”
By Command —
MAJOR GENERAL HARMON
Signed:
M.F. TWINING, Brigadier General
U.S.A. Chief of Staff
March 7, 1943
Second citation — “By direction of the President — A bronze leaf cluster in lieu of an additional Air Medal is awarded by the commanding general of the U.S. Air Forces in the Southern Pacific area to Jesse N. Olmstead, Sergeant — then Corporal — for meritorious achievement in air flight on December 16, 1942 over the Solomon Islands. Corporal Olmstead was assistant radio operator for the flight leader on a successful bombing mission with six B-17s (Flying Fortresses) 16 enemy fighters attached the formation. Wingman No. 3 was disabled early in the encounter, and bomber in which Corporal Olmstead was a crew member with the remainder of the formation, stayed over and to the rear of the disabled bomber, thereby preventing complete destruction and loss of Wingman 3, which finally crashed with little injury to the crew who were finally rescued. At least four enemy fighters were destroyed.”
Command
MAJOR GENERAL THOMAS
A.J. BARNETT,
Brigadier General, G.S.C.,
Chief of Staff
Memorialized Manila American Cemetery and Memorial, Capital District, National Capital Region, Philippines Tablets of the Missing
Honor 
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