Raymond Leonard Callaway, Sr.

Air Force Badge
  • Name: Raymond Leonard Callaway Sr.
  • Location of Birth: Granite Falls, Minnesota
  • Date of Birth: April 12, 1916
  • Date of Death: February 19, 2005 (88 years old)
  • Parents: Raymond Leonard Callaway and Eleanor (Day) Callaway Holle
  • High School and Class: Paynesville Area High School, Paynesville, Minnesota
  • College:
  • Highest Rank: LT COL (Lieutenant Colonel)
  • Branch: Air Force
  • Other Branch:
  • Date Sworn In:
  • Place Sworn In:
  • Date of Discharge:
  • Place of Discharge:
  • Military Awards:
    Purple Heart
    Distinguished Flying Cross
    Asiatic Pacific Ribbon with two Bronze Stars
    American Theater Ribbon with one Bronze Star
    Authorization to wear the Pilot Badge of the Chinese Air Force

  • Military Highlights:
    Raymond was appointed a cadet in the new Army Aviation Cadet Program in March, 1941. He graduated from flying school as a Second Lieutenant on December 12, 1941. He spent 4 1/2 years on active duty as a fighter pilot. Ray served 19 months in China with General Claire Chennault's Chinese American Composite Wing, the "Flying Tigers". Ray became a Fighter Ace, downing 6 1/2 craft in aerial combat in his P-40. Battles and campaigns Ray participated in included those in China, India, Burma, and submarine patrol. Raymond returned to civilian life in September, 1945, but remained in the Air Force Reserve, retiring in 1965 as Lieutenant Colonel.

    News article from Grand Rapids Herald Review, dated February 27, 2005:
    "Shirley Callaway, the widow of Raymond Leonard Callaway, World War II flying ace, was presented with a folded United States flag during the burial ceremony for her husband, which took place at the Itasca Calvary Cemetery on Wednesday, February 23, 2005. Raymond Callaway was a member of the famed "Flying Tigers," from 1943 to 1944. He downed several planes in aerial combat and receive two Bronze Stars and a Purple Heart in addition to other medals for exemplary service. Two F-16 airplanes received clearance from the Pentagon to fly over the Itasca Calvary Cemetery on Wednesday, February 23, 2005, in honor of World War II flying ace, Ray Callaway who died Saturday, February 19 in his home in Grand Rapids. Callaway served 19 months in China with General Claire Chennault's Chinese American Composite Wing, the "Flying Tigers."

    Information in the United States, World War II Draft Cards Young Men, 1940-1947:
    Name: Raymond Leonard Callaway
    Gender: Male
    Race: White
    Age: 24
    Relationship to Draftee: Self (Head)
    Birth Date: April 12, 1916
    Birth Place: Granite Falls, Minnesota, USA
    Residence Place: Grove City, Meeker, Minnesota, USA
    Registration Date: October 16, 1940
    Registration Place: Grove City, Meeker, Minnesota, USA
    Employer: Dale Ruyter Brothers
    Height: 5' 8"
    Weight: 145
    Complexion: Light
    Hair Color: Brown
    Eye Color: Blue
    Next of Kin: Eleanor Gertrude Holle (mother)

  • Wars Involved:
    World War II

  • MIA / POW:

  • Civilian Life:
    Five days after graduating from flying school,Raymond was married to Shirley Joan Wedlock of Aitkin, Minnesota on December 17, 1941 at the Post Chapel at Foster Field in Victoria, Texas.

    In civilian life, Ray worked mostly in construction as a heavy equipment operator and was also a master mechanic and carpenter. He worked for two years as a mechanic during the building of the Alaska Pipeline.

    Ray lived for twenty-three years in Prior Lake, Minnesota retiring to Grand Rapids, Minnesota in 1984 "to take it easy".

    He was a charter member of St. Andrew's Lutheran Church in Grand Rapids, Minnesota, a member of the Civil Air Patrol in Grand Rapids, Minnesota for four years, was a highly skilled woodworker, loved to play cribbage, enjoyed fishing and gardening, getting up early, and long-distance driving (many times driving to Alaska to see his children and their families). Ray was also a longtime fan of the "Flying Berg", Charles Lindbergh.

    Ray was preceded in death by his parents; a daughter-in-law, Lynda Callaway; three sisters and their husbands, Betty (Sawyer) Shelp, Margaret (Rodney) Nelson, and Carol (Ralph) Paulson.

    He is survived by his wife of 63 years, Shirley; sons, Ray Callaway, Jr. and Roy (Dolly) Callaway; daughters, Kathy Callaway, Leslie (Ray) Hobson; a brother, Douglas Holle; two sisters, JoAnne Holle and Helen (Ted) Swanson; five grandchildren; and numerous nieces and nephews and their families.

    Family and friends send our hero a proud and loving farewell, with the Lord Our Savior "guarding his six."

    Buried in Itasca Calvary Cemetery in Grand Rapids, Minnesota. (Plot I-G-08-2-2)

  • Tribal Affiliation(s):