Last of the 7 Bailey Brothers was Tuskegee Airman

Lt. Charles P. Bailey Sr. of Punta Gorda, Fla. in 1943 upon graduating as a Tuskegee Airman. The Germans called his all-black 99th Fighter Squadron the “Black Birdmen.”  Photo provided

Lt. Charles Bailey, Sr. was the last of the line. He was the last of Punta Gorda, Fla.’s “Fighting Bailey Brothers.” The last of a family of seven sons and two daughters who distinguished themselves in war and in life during World War II, Korea and much of the 20th Century.

Charles was the first black aviator from Florida to become a Tuskegee Airman. He is credited with shooting down two Focke-Wulf-190 German fighter planes in “Josephine,” a P-40 Warhawk named for his mother, and later in “My Buddy,” a P-51 Mustang named for his dad.

“At 1425 hours (2:25 p.m.) on the afternoon of Jan. 27, 1944 Lt. Bailey caught an FW-190 headed in the general direction of Rome with a 45-degree deflection shot (from his P-40). The pilot was seen to bail out,” a 99th Squadron Mission Report reads.

Lt. Charles Bailey in his flying gear with his boot on the wheel of the P-51 Mustang named for his father. He shot down a German fighter flying this plane while serving in the all black 99th Fighter Squadron in Europe during World War II. Photo provided

“On July 18, 1944, 10 days after Charles started flying a P-51, the 99th Fighter Squadron flew its second combat mission as part of the 15th Air Force. During that flight, Capt. Edward L. Toppings and Lt. Charles P. Bailey destroyed one FW-190 apiece,” the Air Force records indicated.

Bailey was an early member of the 99th Fighter Squadron. The squadron is famous for never losing an Allied bomber to enemy fighter planes during World War II.

Charles was one of only 450 black pilots who saw action during the war. The 99th Squadron was assigned to the U.S. Army’s 12th Air Force in Europe together with the 100th, 301st and 302nd black fighter squadrons.

Charles’ fight with the Luftwaffe began in North Africa. He flew 133 combat missions over enemy territory. Charles and his squadron also saw action in Sicily, Naples-Foggia, Anzio, Rome-Anzio, Normandy, Northern France, Southern France, North Apennines, Rhineland, Central Europe, the Po Valley and the EAME Theatre in Germany.

During World War II, 66 Tuskegee pilots were killed in action and 32 became prisoners of war. The black airmen received 150 Distinguished Flying Crosses, Legions of Merit and Red Stars of Yugoslavia.

Before the war, Charles graduated from all-black Howard Academy in Ocala. There was no black high school in Charlotte County. So he lived with family in the Ocala area while going to high school there. For two years, in the late ’30s, Charles was enrolled at Bethune-Cookman College in Daytona Beach, one of the few black institutions of higher learning in the state 70 years ago.

While in college Charles enlisted in the Army Air Corps. On April 29, 1943 he earned his wings and gold second lieutenant’s bars upon graduation form aviation cadet training at Tuskegee Institute, the premier black college in Alabama. A month later, when the 99th Fighter Squadron shipped out to take part in the Allied Invasion of North Africa, Charles was one of the squadron’s pilots.

After the war, he returned to Bethune-Cookman to complete his final two years. He received a degree in elementary education. Charles married Bessie L. Fitch of Punta Gorda in 1946. They had two children, Charles Bailey, Jr. and James A. Bailey. Later he also graduated from the Cincinnati College of Embalming. Eventually the family moved to DeLand, Florida where Charles Sr. taught school for decades. When he retired from teaching he opened the Charles P. Bailey Funeral Home in DeLand.

Lt. Carl A. Bailey stands beside the F-84 Thunderjet he flew over the Punta Gorda, Fla. water tank in the 1950s to let his family know he was home again. Photo provided

Lt. Carl A. Bailey 1st black jet pilot in Florida

Lt. Carl A. Bailey was the youngest child. He was born Sept. 1, 1929 and died Nov. 23, 1957.

Carl didn’t serve in a segregated unit like his older brothers in World War II. He was a member of the integrated U.S. Armed Forces. He was one of two black jet pilots from Florida, at the time, who flew F-84 Thunderjets in the early 1950s.

He flew jet fighters at the end of the Korean War after attending Florida A&M University in Tallahassee, Fla.

“He wasn’t actually in the war,” his nephew Maurice Bailey recalled. “He joined up too late.”

“Some of the older folks around town can tell you about him flying over the Punta Gorda water tower in his jet fighter back then,” his nephew added. “The water tower was right next to where his mother lived in those days.”

At 28, and still in the service, Carl was killed while on vacation in an auto accident near Fayetteville, N.C. He is buried next to his father and mother in the Cleveland cemetery, east of Punta Gorda, named for him. Carl never married or had children.

Maurice M. Bailey buried in Arlington

Maurice Bailey

Sgt. Maurice M. Bailey is buried in Arlington National Cemetery in Arlington, Va. He served his country in World War II and in Korea.

Born on May 16, 1906, Maurice was the eldest of the nine Bailey children.

Maurice’s son said he entered the Army after graduating from Florida A&M University. He married his wife, Olivia, when they both attended college.

In the Second World War, he was a member of the “Red Ball Express,” a primarily black unit that kept U.S. front line troops supplied with fuel, food and ammunition during the fighting in Europe. As the German lines were crumbling, the “Red Ball Express” supplied a surging Allied advance across Europe.

Arthur J. Bailey on Iwo Jima

Arthur Bailey

Cpl. Arthur J. Bailey was a Marine who was at Iwo Jima.

Í don’t know what he was doing there, but he was there,” Maurice’s son said.

His discharge papers don’t give a clue either. All they say is Arthur was qualified to drive a light truck and he saw no combat.

When Arthur was discharged from the Marines, he returned to his hometown of Punta Gorda. For a while he was a cook at a local hotel. Then he went to work for General Development Corp., the primary home builder in Charlotte County after the war.

Legusta Felder, his widow who remarried after his death, said he was next to the youngest of the Bailey children. Arthur was born March 20, 1925. He died Nov. 14, 1959, according to his former wife, who still lives in Punta Gorda. He is buried in the Cleveland Cemetery, named for his younger brother, Carl.

Paul Bailey served as chaplain’s assistant

Paul Bailey

Pfc. Paul Bailey was a chaplain’s assistant assigned to Company D, 2805th Engineering Battalion in the Western Pacific during World War II.

While in the Army, Paul received the Good Conduct Medal, the APTO Medal and the World War II Victory Medal.

After the war, he earned a degree in music at Betehune-Cookman College in Daytona Beach, Fla. He also graduated from the Boston Conservatory of Music.

“He could play the piano beautifully,” his cousin Margaret Johnson recalled.

She said he went on to become a high school music teacher. For years he taught music in Madison County near the Florida-Georgia border. Paul retired in the 1970s and returned to Punta Gorda to live with his widowed mother until he died on April 2, 1987. He is buried in the Cleveland Cemetery. Born Sept. 3, 1922, he was the sixth Bailey sibling.

Berlin J. Bailey Sr. on Guadalcanal in WW II

Berlin Bailey, Sr.

E-4 Berlin J. Bailey, Sr. was a member of the U.S. Navy’s 3rd Construction Battalion who served in the Pacific Theater during the war. He was at Guadalcanal, the scene of one of the major island battles in the South Pacific.

Berlin was an electrician’s mate 3rd class, a trade that served him well after he was discharged from the service.

When he returned from war, he established an electrical business in Punta Gorda he operated for more than 50 years. In 1960, Berlin was named to the Charlotte County Citizens’ Committee on Education. From 1976 until 1983, he sat on the Punta Gorda Planning Commission.

Lorene, his second wife, taught school in Charlotte County for 33 years.

Berlin has one son, Berlin J. Bailey, Jr., from his first marriage.

Berlin Sr. died Jan. 6, 1997. He is also buried in the Cleveland Cemetery. He was the second-born Bailey child. He was born Nov. 24, 1912.

Harding Bailey served aboard USS Mason

E-5 Harding C. Bailey, Sr. served aboard the USS Mason, a destroyer escort, during World War II, according to his son Harding, Jr. His father was an electrician’s mate 2nd class.

What made the Mason unique is that it was the first Navy ship with a predominately Negro crew, the Dictionary of American Fighting Ships says. The Mason served in the Atlantic and the Mediterranean.

Harding Bailey

Following his military service, Harding, Sr. became an educator. He began as a teacher and retired a principal in the Brevard County School District on Florida’s East Coast.

Harding is the fifth-born child of the Bailey siblings. He was born Oct. 2, 1920 and died Aug. 31, 1984.

He and Ozie, his college sweetheart, married after they met as students at Bethune-Cookman. They had two children, Harding, Jr. and Burdette. The couple’s marriage did not last. They divorced and later Harding, Sr. married Corrine.

Bailey family descendants and other relatives say the brothers did not tell war stories. They also say the brothers’ demeanor before and after their military experiences reflected their up bringing.

“They were straight-laced,” Burdette Cain, the 45-year-old daughter of Harding, Sr. explained from her Melbourne, Fla. home. “They had the value of respect and family life.”

Margaret Johnson remembers the Bailey children were brought up in a religious household and were ardent supporters of the Bethel A.M.E. Church in Punta Gorda.

Maurice Bailey was a church benefactor even after he moved away. He is responsible for the existing entrance doors on the century-old church.

“He came down here and paid for them,” Johnson said.

Since Bailey descendants followed in their elders’ footsteps, Maurice’s son, Maurice, Jr., enlisted in the Air Force. Harding Jr. is an Army veteran of the Vietnam War.

In 1995 Marcia Bailey, Maurice’s  granddaughter, graduated from the U.S. Naval Academy at Annapolis, Md. Like her forefathers she carried on the military tradition of the Baileys of Punta Gorda.

“I remember Charles’ parents, Archie and Josephine Bailey,” Leo Wotitzky, a long-time Punta Gorda attorney and native said. “Archie was an electrician and plumber. If anyone wanted anything fixed you called Archie.”

People who knew the Bailey brothers credit their parents, Archie and Josephine, for instilling in their children high standards. They pose with their children and daughters-in law in the photo above. From the left kneeling in the front row: Charles, Carl, Berlin and Harding. Standing at left: Maurice, Josephine, Maurice’s wife, Olive, and Archie. Photo provided

Charles and his six brothers and two sisters grew up in Charlotte County during the 1920s and ‘30s. They fought for freedom, a basic right none of them completely enjoyed when they took up arms for this country. That fact wasn’t lost on them, but it didn’t stop Arthur, Berlin, Carl, Harding, Maurice, Paul and Charles from enlisting in the Army, Navy, Marines, Army Air Corps, and Air Force.

Charles died on April 9, 2001. He is buried in Greenwood Cemetery, Daytona Beach, Fla. He was 82.

“We had to fly until we dropped or were shot out of the skies,” Judge Robert Decatur of Washington, D.C., one of the  principal speakers at his funeral, told mourners. Like Charles, he was a member of the Tuskegee Airmen.

Charles was buried with full military honors, including a flyover by four F-15 jet fighters station at Patrick Air Force Base, Cape Canaveral, Fla. The fighters swooped over his grave in the “Missing Man Formation” signifying the loss of a fallen comrade.

“Just before the planes went over, a big wind came up. It was like something from heaven,” said Marguerite Johnson, a second cousin of Charles who attended the funeral.

Bailey’s File

Name: Charles P. Bailey
Age: 82 (deceased)
Address: Daytona Beach, Fla.
Hometown: Port Charlotte, Fla.
Discharged: 1947
Rank: Lieutenant
Unit: 99th Fighter Squadron, 15th Air Force
Commendations: Distinguished Flying Cross, Air Medal with four oak leaf clusters, Presidential Unit Citation, World War II Victory Medal
Married: Bessie Fitch
Children: Charles Jr. and James.

This story was first published in the Charlotte Sun newspaper, Port Charlotte, Florida on May 27, 2001 and is republished with permission.

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  1. How truly awe inspiring. It was very hard for me to hold back the tears while reading of this incredible, courageous family of warriors. I am so very proud to be a part of the greatest country in the world, and to read these stories makes me feel safe and sound in my bed at night, thanks to people like Charles Bailey and all of the heroic Bailey’s. I can never thank you in person, so perhaps someone will read this letter from a 51 yr. old woman from Western NY, who’s father served valiantly in the Battle of The Bulge. He just died on Jan. 2nd of this year. When that happened, I thought of all the men and women who fought so very hard for our freedom and most assuredly put their lives on the line for total strangers, but all for a common cause. Freedom. Apparently, they all thought it was well worth it. I, and my entire family are eternaly grateful to all of the Baileys .God Bless and keep you all. Most sincerely, Lizzie Grey Brockport, NY

    • Lizzie,
      I’m glad you liked the Bailey brothers story. Their exploits in WW II were something else, but what they accomplished afterwords was truly incredible.

      Most of them became school teachers at a time before integration in Florida. That meant they couldn’t go to high school locally even though they lived two blocks from the local high school and they had to start off teaching in an integrated school system.

      None of this seemed to bother them. They thrived and became not only respected teachers but in some instances principals.

      What a family.

      Please keep reading “War Tales.” There are lots of other great stories coming up with pictures to support them.

      Don Moore
      Sun Newspapers

      • “None of this seemed to bother them” are you serious? What do you think they talked about at dinner? What do you think they had to do to protect their families, and get them opportunities to live a good life. What do you think they did when turned away at voting polls? And lastly, do you imagine that they cried at the thought of loosing friends and family who were sacrificed to preserve the American status quo. You bet it bothered them, and still bothers their kids, just ask before you assume.

  2. Proud to have known the Baileys, while growing up in Punta Gorda in the 1970’s. Excellent story!!!! “Ms Josephine” as she was lovingly known as, was a wonderful woman. I can still hear Mr. Paul Bailey on the piano!

    • What the seven Bailey brothers did in the service during World War II and Korea was impressive. But what they accomplished as teachers and principles after the war was even more impressive. They were role models for all of us.

      Don Moore

  3. I am a proud descendant of the Bailey brothers being my great uncles I never had the opportunity of meeting all of them however the few that I did have left a lasting impression on my heart. They served our country and I will forever be grateful by continuing to carry on their last name.

    • Carmen, Your kinfolk were not only very unusual since all seven of them were in the service, 6 at the same time. And they were serving at a time when their country didn’t allow them the right to vote. Amazing! But better than all that, after they got out of the service almost all of them went into education making their lives and the those they taught better. It doesn’t get any better than that. Regards, Don Moore Sun Newspapers War tales

  4. Author Bailey is my great grandfather, so blessed and proud to come from me African American family brothers, and Uncles all in different branches I’m glad to come from success family I’m proud to be American…

    • Tyris –

      Those seven men were indeed, remarkable, especially if you consider the times when they came of age. It could be said the legacy they leave is more important than what they did when they were in the service. You come from good stock, and it’s good to know you recognize the importance of your heritage.

      Thank you for reading and commenting on War Tales.

  5. I have two adult children that are grandkids of Harding Bailey Sr. Although I knew their dad, Harding Jr., served time in Viet Nam, it was many years before I knew the legacy that had been left by their grandfather and brothers, which is something to feel blessed by.

  6. Hi Don, let me start by saying that I enjoyed reading all of the nice things people were writing about my family. It was a pleasure meeting you at the airport dedication in Punta Gorda. It was a great day. That was awesome having the Marine Corps Honor Guard there, and I was literally blown away to find out the commander was General Bailey. (not related) Well my friend, there’s only one left of that generation. My aunt Mrs Lorene Bailey, who incidentally was my third grade teacher at Baker Academy. Again Don, great job!!

    • You or someone else might want to put a video camera in front of your aunt and start asking her questions. That would be a great Christmas gift to her family. Email everyone asking input on what questions to ask. Have that list in hand so questions aren’t forgotten.

      It was my pleasure to write about your father and uncles. They were a remarkable bunch.

  7. Authur Bailey is my great grandfather.. proud to come from a family that supported this country.. RIP pop.. and to my uncle’s too

  8. Mr. Charles P. Bailey was my 4th grade science & social studies teacher in 1984-85 at Altamonte Elementary School. We did not know of his military service at that age, but all the children loved him! He was kind, fun, and inspiring. He was a finalist to be the first teacher in space, which was during my time in elementary school. What an amazing family he had, too!

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