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703. Milton's October Loss 10-10-1944 WWII

Updated: Mar 3, 2022

US Army Private Henry Oliver Cassady was born in Atmore, Alabama on October 9, 1922, the son of Augustus "Gustus" Laprade Cassidy (1882-1955) and Oreleus Mary (Ora Mae) Seale (1887-1975). His parents were married on January 12, 1908, in Conecuh County, Alabama. They would begin making their way south by way of Atmore and Brewton. By 1930, Henry and his family were living at 324 Dixonville Rd. in Brewton while his father supported the family as a farmer. Note, the 1930 Census was the only one that noted whether families owned a radio or not. This was to determine the nation's new interest in consumer behaviors as well as methods of mass communication for the future. Sadly, the Cassady family did not own this luxury! By 1940, the entire family was living with their son James Russell who was a local farmer in Santa Rosa County. James and his wife Marie were renting a house for $15.00 per month and sharing it his parents and sibling. In 1941, Henry was listed as working for the Gulf Shipbuilding Corporation in Chickasaw, Alabama as a ornamental metal worker.


Henry was also the great grandson of John Calvin Cassady (1825-1884), a Confederate soldier with Company "H" of the 4th Alabama Infantry Regiment. He had been conscripted on July 2, 1864, so he had little choice in whether he wished to fight or not. The Confederacy's Third Conscription Act was passed on February 17, 1864, which stated all white men between 17 to 50-years old would become available for military service for an unlimited period. There was also a provision that anyone 17-18 years and 45-50 years old, were allowed to enter their state's defense reserve rather than the regular army. Unfortunately, John Calvin was 38 years old! As it were, his regiment was assigned to General Longstreet's Corps who had already fought some of the bloodiest battles in American history. By the time he joined his regiment they were already fortifying themselves during the siege of Petersburg, Virginia. The Confederate troops there were starving and the casualties horrendous as shown in the 1st Battle of Deep Bottom and the Battle of the Crater. At that time, John deserted to the Union lines on August 7 and survived the war.


Then came WWII and Henry Oliver's enlistment on October 28, 1943, before reporting to Camp Blanding, Florida for processing and orientation. After basic training, he was assigned to the Headquarters Company of the 349th Infantry Regiment, 1st Battalion, 88th Infantry Division. He was "one of the first fathers to enlist from Allentown" and left behind his wife Wynell "Nell" Edwina Stokes (1925-2000) and his young son Henry Gerald Cassady. He had married Nell on February 13, 1943 in Milton, the daughter of Samuel T. and Lala P. Stokes.


Henry arrived in Italy in April 1944 and his unit was thrust into the campaign to take control of Northern Italy. In September 1944, the 88th Infantry Division used the 349th Infantry Regiment as a rapid advance column to spearhead the drive north to Bologna. After a fierce firefight, the 1st Battalion cleared out the town of Belvedere, Italy and by October 2nd they controlled a ridge line that overlooked the German positions. It was in this vicinity that Private Cassady was killed in action on October 10, 1944.


After his death he was buried in a military cemetery in Italy while his wife and family were notified of his passing. After the war, his wife requested his body be returned to Milton at no costs to the family. On November 19, 1948, Henry was buried in the Calvary Baptist Cemetery with full military honors. Wynell would remarry in Milton on August 30, 1948, to Earlie Linzy Jr. (1923-1988), son of Earlie Sr. and Sarah Justice. Linzy had served himself in WWII and was a German prisoner of war. He would retire from the Escambia River Electric Corporation prior to his death. After his passing, Wynell would marry Buell Davidson who survived her.


Postscript: The son he never met went on to serve in the US Army with the 101st Airborne Division and following his service he became a police officer with the Pensacola Police Department. He retired after a long, distinguished career of 34 years plus seven more with the Florida Department of Juvenile Justice. He was the first officer with the PPD to receive the "Medal of Valor." Henry Oliver's grandson Jeremy followed his father into law enforcement with the Escambia County Sheriff's Office. His granddaughter Dana Cassady also served with the 101st Airborne Division in the Gulf War and currently serves in the Army Reserves. It is a great honor for the Santa Rosa community to have three generations of Cassady's that have served their country so well!


















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