WC native son one of famed Tuskegee airmen

Middleton-Esters family had long tradition of military service

Maurice Esters

This article originally appeared in the Daily Freeman-Journal in 2015, written by local historian Nancy Kayser. It is reprinted here in observance of Black History Month.

There were fewer than one thousand African-American Tuskegee airmen during World War II. The pilots, training under rigid military segregation, became one of the Nation’s most fabled war-time units.

One of them, Maurice Vincent Esters, was born and raised in Webster City. He carried on the tradition of serving his country begun by his grandfather, Nathan Esters Middleton, who was born a slave in Shelby County, Kentucky around 1838.

After emancipation, Middleton joined the 109th Kentucky Regiment, United States Colored Infantry at Louisville, Kentucky in June of 1864. He served with the unit until mustering out in March of 1866.

His December 1867 Freedman’s Bank application at Louisville, Kentucky under the name Nathan Estes, records his history, listing his master as Henry Estes and his Mother as Lilah Middleton, then of Paris, Edgar County, Illinois.

Esters-Middleton, the name he chose to use, was a horseman, training Standardbred trotters and pacers. His occupation took him to Grandview, Edgar County, Illinois by at least 1870, moving to nearby Charleston, Coles County, Illinois by 1880. He likely joined other family members already settled in the area.

These central Illinois counties were a mecca for harness racing and Nate Middleton, as he was known, would have found steady employment. One of his employers was Dr. J. W. Neal, physician and later editor of the Western Horseman racing magazine.

When Nate Middleton came to Webster City, Iowa is uncertain, but it was definitely linked to the town’s Driving Park and large cluster of citizens raising and owning sport horses. Middleton leased the Driving Park in early 1887, married Scottish born Jane Hawkins Hays and settled into his horse training life in Iowa.

He and his family, which now included a son Charles “Chic” Middleton, continued to live in Webster City, returning to Illinois many times over the years to train for that state’s horse owners.

Even when he was training horses out-of-state, Nate Middleton – “that black republican” – as the Hamilton County Journal called him, always made a point to return to Webster City to exercise his newly gained right to vote. He was also active in the local Grand Army of the Republic (GAR), a group of Civil War veterans.

In the late 1890’s, Nathan Esters Middleton was selected to be a janitor during at least two Iowa Legislative terms. His health declined in early 1903 and his local GAR comrades escorted him to the Iowa Soldiers Home in Marshalltown for care. Middleton died there in June of 1903 and was buried in their Veteran’s cemetery.

Carries on tradition

Charles “Chic” Middleton, son of Nathan and Jane Middleton was born in Webster City in 1890. He carried on the family’s military tradition by joining the local Company C, Iowa National Guard by at least 1908. While he served as the unit’s cook, he was also an expert sharpshooter, winning the National Guard state championship 800-yard shoot in 1915.

When Webster City’s Company C, Iowa National Guard, was federalized in mid-1916 for the Mexican Border War, “Chic” Middleton went with the unit to Des Moines for additional training. It was there he was informed, according to the Webster City Tribune, “as the only colored member of Company C, he would not be allowed to go the Mexican border with the white company, but would have to join a colored regiment in Illinois, if he went”.

Hamilton County newspapers were indignant and editorialized extensively against the federal military’s discrimination rules. “Chic” Middleton returned to Webster City, while his unit went on to serve guard duty along the Mexican border.

Charles “Chic” Middleton legally changed his last name to Esters in 1912, but the local newspapers continued to refer to him under both last names.

Charles Middleton Esters did serve briefly during World War I with the 6th and 19th Battalions, 163th Depot Brigade at Camp Dodge, near Des Moines.

Two sons

The two sons of Charles Middleton Esters and his wife Idena were born in Webster City – Charles H. Jr. in 1919 and Maurice V. in 1921. Both boys spent their teen years at the Iowa Soldiers Orphans Home in Davenport because of their parents’ legal skirmishes. On graduation at age eighteen, both returned to their hometown to live.

All male citizens, ages 21 to 36, were required to register in the fall of 1940 under the peacetime conscription act. Charles H. Esters, Jr. received number 757, but he didn’t wait to be drafted. He enlisted in the Army Air Corps in January of 1941. After training as an airplane mechanic at Chanute Field in Illinois, he was assigned to the 11th Air Force group and served in the Aleutian campaign. On return to the U.S., he went with the 497th Bombardment Group, 20th Air Force for duty in the Northern Mariana Islands. Esters, who later made his home in California, remained in the Air Force, retiring in 1970.

Brother, Maurice Vincent Esters, meanwhile, attended Webster City Junior College and worked as a bellboy at the Willson Hotel. He was well liked and excelled as a baseball player. Newspaper reports show he was an outstanding student in chemistry. Local residents still recall Maurice saying “he was holding out to join the Tuskegee flyers”, an African-American Army Air Corp group first authorized in January 1941.

Maurice V. Esters, who had signed up for training as a cadet flyer, received his call to join the Air Corps on August 10, 1942, just two months after he turned twenty-one. He received training at Fort Riley, Kansas, Selfridge Field in Michigan and the Tuskegee Institute in Alabama.

Awarded his wings

On May 28, 1943, Maurice V. Esters was awarded his wings and commissioned as a 2nd Lieutenant. His last trip home to visit Webster City was in December of 1943.

Esters was assigned to the 301st Fighter squadron, part of the 332nd Fighter Group, which departed for overseas duty from Hampton Roads, Virginia on January 3, 1944 in a four-ship convoy. The 301st rode aboard the SS Clark Mills (HR-812) stopping briefly in North Africa on their way to a permanent station in Italy.

Flying out of a base at Montecorvino, Italy under command of the Twelfth Air Force, the 301st went into combat for the first time in mid-February 1944. The unit flew escort missions for the B-17 and B-24 bombers.

After stationing on several temporary bases, Ester’s unit, the 301st, was moved in late May of 1944 to Ramitelli Airfield in Italy near the Adriatic Sea. The former wheat field had a 5,500-foot long steel planking runway which was only 150 feet wide. A farmer’s house served as the group’s headquarters.

It was also at this time the group began transitioning to the Republic P-47D Thunderbolt fighter.

Maurice V. Esters was assigned to a used P-47, serial number 42-75958, from the 325th Fighter Group. The plane had been shot up in combat, rebuilt and returned to duty.

On June 26, 1944, the 332nd Fighter Group flew a bomber escort mission to the Lake Balaton area of Hungary. While the group lost no bombers on that trip, they did lose two of their unit’s fighter pilots – one was Maurice V. Esters of Webster City.


Recently declassified Missing Air Crew Report No. 7061 details the loss of fighter pilot Esters, just recently promoted to 1st Lieutenant. Fellow pilot Charles A. Dunne reported that Esters’ plane developed engine trouble about ten minutes from home shore. Esters broadcast a “Mayday” call and then bailed out. Dunne stated that he followed his parachute down and saw Esters climb into his dinghy and release a green oil marker on the water. Being short on gas, Dunne noted the location and returned to base.

The loss occurred about fifteen miles north of the Isle of Vis and was considered hostile territory. There was no recorded search made, as other pilots noted they saw Esters’ dinghy swamped by a large wave.

Maurice V. Esters was listed as Missing In Action. One year and one day after his loss, the Tuskegee pilot from Iowa was officially declared dead as required by war time military regulations.

Esters was the only one of the twelve Iowa Tuskegee airmen to die during World War II. His name is inscribed on the Tablets of the Missing at the Florence Italy American Cemetery and Memorial to honor his service.