James Wilmer "Jim" Bailey

james bailey

September 5, 1948 ~ October 29, 2022

James Wilmer “Jim” Bailey, Jr., 74, of Lusby, MD, passed away on October 29, 2022 at his home. Born on September 5, 1948 in Leonardtown, MD, he was the son of the late James Wilmer Bailey, Sr. and the late Agnes Lorraine Wallace Bailey. Jim married Martha Ann Millikan on November 24, 1971 in Houston, TX. Fifty years married, Jim’s life has been filled with adventure, joy, and the love of family and friends. In addition to his wife, he is survived by his daughters, Elsie Summers (Jason) of St. Mary’s City, MD and Mary Lu Dove (Rick) of Lexington Park, MD, his sisters, Pat Leslie (John) St. Augustine, FL, Glenda Joyce of California, MD, and Franny Bailey of Hollywood, MD, as well as his grandchildren, Natalie, Steven, and Lyra Summers. In addition to his parents, Jim was preceded in death by his sister, Mary Jean Wills and his brother, John Lee Bailey. Jim attended St. John’s Catholic School in Hollywood, MD. He graduated from Chopticon High School in 1967, and enlisted in the Army in 1968; he then served in Vietnam from 1969-1970. He performed the duties of a crew chief/door gunner on gunship helicopters in Wolf Pack in the 281st Assault Helicopter Company. The 281st AHC was the first special operations company in the United States Army. Jim was awarded 17 air medals, including one with “V” Device (for Valor). He participated in Project Delta. When he departed from the Army in 1971, he was a maintenance electrician in Houston, TX. He moved his family to Maryland in 1997. Jim worked from several DOD contractors as a facilities coordinator at Patuxent River Naval Air Station. He was a member of the Knights of Columbus, 281st AHC, The Special Operations Association, The Disabled American Veterans, The Vietnam Veterans of America, and the Southern Knights Car Club. Jim was in the Recycled Bluegrass Band and in the Uncloudy Day Band. He enjoyed performing bluegrass country and gospel music. Jim wrote the song, “Sitting in the Door.” It is a song about him being a chief/door gunner during his tour in Vietnam. Jim enjoyed going to car shows with his 1957 Chevy Bellaire. He had his family childhood car restored and he always said that the 57 looks like it did when he was young. Jim retired in April 2022 from SA-TECH. He enjoyed travelling to Texas, going on a cruise to Alaska, and going to his 281st Army reunion in New Orleans during a three-month span. The family will receive friends on Thursday, November 10, 2022 from 5:00 PM to 8:00 PM with prayers recited at 7:00 PM in the Mattingley-Gardiner Funeral Home, Leonardtown, MD. A Mass of Christian Burial will be celebrated on Friday, November 11, 2022 at 10:00 AM in St. John’s Catholic Church, Hollywood, MD with Father Ray Schmidt officiating. Interment will be at Arlington National Cemetery, Arlington, VA, at a later date. Serving as pallbearers will be Tommy Alvey, Jay Armsworthy, John Brawley, Mickey Dillow, Ray Faulstich, and Randy Stillwell. Honorary pallbearers will be Phil Cameron and Jack Tippett. A Funeral Service will be held on Thursday, March 7, 2024 at 3:00 PM in Arlington National Cemetery Arlington, VA. Contributions may be made to the Hollywood Volunteer Rescue Squad Auxiliary, P.O. Box 94, Hollywood, MD 20636. Condolences may be made to the family at www.mgfh.com. Arrangements provided by the Mattingley-Gardiner Funeral Home and Cremation Services, P.A., Leonardtown, MD.

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  1. Diana Huntt McConnell says:

    So sorry to hear of Jimmys passing. A classmate and friend of sister, Pat. A good man and a great loss. Deep condolences to family and friends.

  2. Katherine and Thomas Bean says:

    We are very sad to hear of Jim’s passing! He will be missed by us and all those who knew him as a loving, gentle man with a big heart who loved to make music!

    I’ve messaged Marina and she and Natasha are grieving too!

    May God grant peace to all who mourn Jim’s loss! We are praying for you all and offer our love always!

    Kathi and Tom Bean

  3. I really enjoyed all the times I heard your music, Glenda & I spoke often about wanting to get back our to hear some more, seems we always missed out.May your heavenly band bring a smile to our Lords face as he gets to hear what he has wrought,another voice that can be added to a ll of the otherBailleys & Wallace’s that he has already there. GOD Bleas .

  4. Jimmy, may you rest in peace. Always enjoyed your music. A good man always.

  5. Martha – So sorry to hear about Jim’s passing. I haven’t seen you two in quite a while but always enjoyed Jim’s singing and chatting with you. May Jim rest in peace.

  6. So many thoughts and prayers are being sent to each of you . I will never hear Walk across Texas without thinking of Jim and of course you Martha. Hope you know will always love you Martha and of course Jim
    to the moon and back xo
    Linda Muller

  7. Tism Thompson Blackwell says:

    To all of the Bailey family – I’m so sorry for your loss. I always remember Jimmy as a kind person. Sympathy to you all – Tism Thompson Blackwell

  8. Ruth Joy Coombs / Betty Joy Thomas says:

    Martha and all of Jim’s Family: So sad to hear of Jim’s passing. Martha, you and Jim were so warm and welcoming and it was always a joy to be in your presence. May your wonderful memories give you peace during this time of great loss. Our most heartfelt thoughts and prayers are with you.

  9. Paul and Patti Lincoln says:

    With a heavy heart we send our prayers of peace in this time of loss to Jim’s family. We always enjoyed listening to Jim sing and play his guitar. He was so kind and welcoming to us as we joined the family at Mt Zion every other Thursday. Prayers and hugs!

  10. I first enjoyed Jim and Jay playing and singing in Recycled Bluegrass and will always remember his amazing talent, was so inspiring to me! Sending the family my condenses and love!

  11. Dear Martha

    Although we have never met in person you have been a dear and precious FB Friend. I was very saddened by your message today telling me about Jim. I can’t express how sorry I am for you and the family. This is a loss that I have not had in my life yet…the loss of a husband. Please know that you will be in my thoughts and prayers. I am thankful for your friendship.

    Love You ❤
    Glenda

  12. So very sorry to hear about Jimmy’s passing. I remember our childhood of course but once he went into the service and I left the County for Rhode Island we lost contact. He was a great person from a great family and will be sorely missed by many. R.I.P. Jimmy.

  13. As a member of The Unclouded Day, it was my honor to perform with Jim and he was an awesome performer and a very nice guy. He was also an excellent storyteller which is required for a singer-songwriter. He will be sorely missed by all who knew him.

  14. Sincerest condolences to the Bailey family. We will miss this old boy. He was a good singer and a great guy. So sad to hear of his passing.

  15. Pat and Myra Pettit says:

    We have been friends with Jim and Martha for over 46 years. They both are so sweet, kind and thoughtful! Jim was a patriot, talented musician, dear friend, and wonderful husband and father. He will be greatly missed by all. Our love and deepest sympathy goes to Martha and family.

  16. I WAS SO SAD TO HEAR THAT MR. BAILEY HAD PASSED AWAY.IVE KNOWN MARTHA FOR A LONG TIME. PRAYERS FOR HER AND HER FAMILY. REST IN PEACE

  17. I worked with Jim for several years. He was such a nice and gentle man. My thoughts and prayers are with you during this difficult time.


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