Corporal Caleb O. Simpler (1917–1942)

Caleb O, Simpler in 1941 or early 1942 (Courtesy of the Delaware Public Archives)
Home StateCivilian Occupation
DelawareBank employee
BranchService Number
U.S. Army32167222
European, AmericanBattery “H,” 61st Coast Artillery Regiment (Antiaircraft)
Purple HeartBattle of the Atlantic

Early Life & Family

Caleb Oliver Simpler was born in Felton, Delaware, on the evening of March 10, 1917. He was the second child of Clifford Morris Simpler, Sr. (a bank cashier, who at other points worked as a school superintendent and ran a lumberyard, 1885–1966) and Caroline “Carrie” Simpler (née Caroline Hammis Angstadt, 1887–1969). He was born half an hour after his twin brother, Clifford Morris Simpler, Jr. (1917–1936). Caleb and Clifford also had a younger brother, J. Barratt Simpler (who served in the U.S. Navy during World War II, 1922–1967), and a younger sister, Caroline Simpler (later Abbott, 1923–2016).

The Simpler family was recorded on the census on January 2, 1920, living at 10 Church Street in Felton. The Simpler family was still living on Church Street at the time of 1930 census. As a teenager, Simpler’s twin brother was stricken with kidney disease and anemia. C. Morris Simpler, Jr. died in Felton on February 26, 1936, shortly before his 19th birthday.

Simpler in The Blue Hen yearbook (Courtesy of the University of Delaware, enhanced with MyHeritage)

Caleb O. Simpler attended the University of Delaware, where he was football team manager. He was also a member of the school band, the Athenaean Society, and the Sigma Phi Epsilon fraternity. After graduating from college in 1938, he began working at the Equitable Trust Company. Simpler was recorded on the census on April 25, 1940, living with his family in Felton and working as a bookkeeper. A 1940 Wilmington directory and his draft registration card, dated October 16, 1940, gave his address as 1019 Park Place in Wilmington, Delaware. The draft registration card indicated that he moved to 304 Marsh Road sometime in the next 11 months.

Simpler’s enlistment data card listed his occupation as financial institution clerk. Simpler’s military paperwork described him as standing five feet, 8¼ inches tall and weighing 137 lbs., with brown hair and brown eyes. No religious preference was recorded.

Military Career

Simpler was drafted before the U.S. Army entered World War II. He was inducted on August 7, 1941, in Trenton, New Jersey, and assigned to the Coast Artillery Corps. C. B. Simpler wrote that his son began training at Camp Wallace, Texas, in September 1941. According to a document in his Individual Deceased Personnel File (I.D.P.F.), as of October 13, 1941, Private Simpler was a member of Company “A,” 29th Coast Artillery Training Battalion at Camp Wallace.

Simpler’s father wrote that on December 6, 1941, his son transferred to Fort Hancock, New Jersey, where he remained until February 17, 1942. Simpler’s military paperwork confirms that he was at Camp Wallace in December 1941 and Fort Hancock in January 1942. Simpler’s father added that his son was promoted to private 1st class in January 1942 and went overseas from the New York Port of Embarkation on February 17 or 18, 1942.

Both Simpler’s father’s statement and his I.D.P.F. listed his unit as Battery “H,” 61st Coast Artillery Regiment (Antiaircraft). Curiously, the regiment’s movements do not line up with C. B. Simpler’s statement about his son’s movements. According to a summary of the unit in Shelby Stanton’s World War II Order of Battle, the regiment was stationed at Fort Sheridan, Illinois, when war broke out. He wrote that the unit shipped out from the New York Port of Embarkation on February 26, 1942. The regiment arrived in Iceland on March 3, 1942.

Several months after arriving in Iceland, Simpler had the opportunity to return to the United States to attend Officer Candidate School (O.C.S.). Simpler’s father wrote that his son was promoted to corporal (as was customary for officer candidates) two days before he sailed home. Travel was hazardous at that time. The Battle of the Atlantic had been in progress since the outbreak of war in Europe in 1939, but the U.S. entry into World War II intensified U-boat activity along the U.S. East Coast.

Corporal Simpler boarded the S.S. Cherokee, a civilian vessel skippered by Twiggs E. Brown (1887–1967), which sailed from Iceland on May 27, 1942. Records indicate there were 169 men aboard the ship: 112 crew members, 11 members of the U.S. Navy Armed Guard manning the ship’s single 4-inch gun, and 46 passengers (43 U.S. Army personnel, two Soviet naval personnel, and a coast pilot). Of the U.S. Army passengers, 36 were earmarked for O.C.S. in the continental United States and six were traveling for medical treatment, with the 43rd man supposed to attend warrant officer music school. The vessel stopped in Halifax, Nova Scotia, joining Convoy XB-25 there for the rest of the voyage to Boston, Massachusetts. Although Cherokee’s top speed was 16–17 knots, she was forced to sail at half that speed to stay with the convoy.

It was stormy on the night of June 15, 1942, with a northwest gale blowing, but the convoy was scheduled to reach Boston on the 16th. About 75 miles east of Boston and perhaps 30 miles northeast of the tip of Cape Cod, steaming at eight knots, the convoy was intercepted by a German submarine, U-87, under the command of Kapitänleutnant Joachim Berger (1913–1943). The submarine fired two torpedoes at S.S. Port Nicholson, followed by two more at S.S. Cherokee.

In testimony before the “C” Marine Investigation Board of Boston on June 18, 1942, Third Mate Edwin R. Kremer, Jr. (1922–2001) stated that after Port Nicholson was hit, he

rung down [to the engine room] “full speed” and gave “hard right [rudder]” to the quartermaster, and then the captain was on the bridge at the time, and he threw on the alarms for the passengers’ quarters and the crew quarters, and I threw in the alarm for the gun crew, and then the captain went to the telephone and told the engine room, “Give her all she’s got. We have been attacked.”

Lookouts and the men manning the 4-inch gun searched the darkness looking in vain for the enemy submarine. Cherokee’s master testified that despite the evasive maneuvers, his ship was torpedoed forward on the port side, followed by a second on the “Port side, aft of amidships[.]”

According to a summary of the incident in a document in Simpler’s I.D.P.F., Cherokee

was struck by two torpedoes within a minute and a half of each other at 2230 15 June 1942 and sank by the bow within seven minutes after the first torpedo struck.  No lifeboats could be launched because of the list but seven life rafts were cut loose.  Of the total of 169 crew members and passengers on board, two were known to be killed and eighty-six were missing.  The first torpedo exploded under the bridge with terrific force, lifting the shift out of the water momentarily and the second struck amidships.  Many were asleep at the time of the attack and did not get on deck in the short time before the vessel went under.

Despite that the heavy seas and the speed with which the ship went down, 83 men (just under half of those aboard Cherokee) were rescued by other ships in the convoy, including 23 of the 43 Army passengers. 86 men died in the sinking, including Corporal Simpler. Several bodies were recovered by other ships in the convoy and buried at sea, while others washed ashore on the coast of Canada. Simpler’s body was never found. Less than a year later, on March 4, 1943, Canadian warships sank U-87 with all hands, including Kapitänleutnant Berger.

Journal-Every Evening reported on March 8, 1946, that a V.F.W. post in Felton was to be named in honor of Corporal Simpler, Technician 5th Grade Loran C. Adams and Private John A. Ware:

Three Delaware men who died in World War II will be perpetuated in the memory of their home town and their schoolday friends when the Adams-Simpler-Ware Post of the Veterans of Foreign Wars is formally dedicated in Felton Sunday afternoon [March 10] at 2:30 o’clock.

Corporal Simpler’s family placed a cenotaph at Barratts Chapel Cemetery in Frederica, Delaware, where his twin brother had been buried. His parents and younger brother were also buried there after their deaths. Corporal Simpler’s name is also honored at the Tablets of the Missing at the East Coast Memorial in New York City and at Veterans Memorial Park in New Castle, Delaware.


Time of Attack

There are some discrepancies in the time of the attack, possibly due to time zones. A summary of the attack in Simpler’s I.D.P.F. gave the attack as about 2230 hours Eastern War Time (Eastern Daylight Time) on June 15, 1942. Captain Brown testified that the ship was torpedoed at around 2321 or 2322. It is unclear if the ship’s clock had been changed over from Atlantic Time by that point or whether the summary was an hour off. An article on, based on German records, stated that U-87 fired two torpedoes at the Cherokee at 0421 hours on June 16, 1942. Presumably that was not adjusted for local time.

Had Simpler sailed a month later, the attack would not have happened (at least not where it did), because the Germans pulled their submarines away from the East Coast in July 1942 as sinkings fell due to Allied convoys and airpower.

Photo Enhancement

The Blue Hen photo on this page was digitally enhanced using tools on the genealogy website MyHeritage. This software is useful in instances where the only known photograph is of limited resolution (due to the resolution of yearbook printing). I believe it to be an accurate reconstruction, but the software could potentially introduce errors by misinterpreting fuzzy details in the original photograph. A comparison of the original and enhanced versions of the photos can be viewed below.

Comparison of the original (below) and the product of MyHeritage’s enhancements (bottom)


Special thanks to the Delaware Public Archives and to the University of Delaware for the use of their photos of Simpler.


The 1937–1938 Blue Hen. Courtesy of the University of Delaware.

Caleb O. Simpler Individual Deceased Personnel File. Courtesy of U.S. Army Human Resources Command.

“Caroline S. Abbott.” The News Journal, October 31, 2016. Pg. 8A.


“Corp Caleb Oliver Simpler.” Find a Grave.

“Joachim Berger.”

C. Morris Simpler death certificate. Bureau of Vital Statistics, Hall of Records, Dover, Delaware.

Caleb Oliver Simpler birth certificate. Record Group 1500-008-094, Birth certificates. Delaware Public Archives, Dover, Delaware.

Clifford Morris Simpler, Jr. birth certificate. Record Group 1500-008-094, Birth certificates. Delaware Public Archives, Dover, Delaware.

“Felton Soldier Among Missing in Ship Sinking.” Wilmington Morning News, June 24, 1942. Pg. 1 and 21.,

Gaines, William C. “Coast Artillery Organizational History, 1917–1950 Part I, Coast Artillery Regiments 1–196.” The Coast Defense Journal, Volume 23, Issue 2.

“New V.F.W. Post at Felton Will Bear Names of Three Dead.” Journal-Every Evening, March 8, 1946. Pg. 23.

Polk’s Wilmington (New Castle County, Del.) City Directory 1940. R. L. Polk & Company Publishers, 1940.

Simpler, Clifford M., Sr. Caleb Oliver Simpler Individual Military Service Record, c. 1946. Record Group 1325-003-053, Record of Delawareans Who Died in World War II.  Delaware Public Archives, Dover, Delaware.

United States of America, Bureau of the Census. Fourteenth Census of the United States, 1920. National Archives at Washington, D.C.

United States of America, Bureau of the Census. Fifteenth Census of the United States, 1930. National Archives at Washington, D.C.

United States of America, Bureau of the Census. Sixteenth Census of the United States, 1940. National Archives at Washington, D.C.

World War II Army Enlistment Records. Record Group 64, Records of the National Archives and Records Administration. National Archives at College Park, Maryland.

WWII Draft Registration Cards for Delaware, 10/16/1940–3/31/1947. Record Group 147, Records of the Selective Service System. National Archives at St. Louis, Missouri.

Last updated on April 26, 2022

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