Stephen Gray Calaway

Stephen Gray Calaway, 78, of Winston-Salem passed away Tuesday September 4, 2018. He was born in Forsyth County February 19, 1940 to Harley Robert and Alice Ball Calaway. Stephen attended Old Town School and then attended Reynolds High School, graduating in 1958. His favorite activity was the marching band where he played the trumpet. He attended Wake Forest University and WFU law school, graduating in 1964. He participated in army ROTC and was a member of Sigma Chi fraternity. He also served as a freshman dorm counselor while in law school. He met Jackie while as fellow students at Wake Forest. They married in1964, Soon after graduating, Steve entered the army and he served as a purchasing officer for Fort Polk in Louisiana. His base trained and sent troops to Vietnam. After serving, he and Jackie returned to Winston-Salem and began the law career he had planned since he was five years old. He tried various types of law and discovered he enjoyed zoning, contracts and real estate transactions best. He was quite involved in political and community life. He and Jackie had Murray and Clint, who both were active in sports which led Steve to being active in various sports organizations. Steve was a member of the Jaycees, and during his membership, the Jaycees and many other community leaders helped develop and build the West Central Community Center. He served on the board at Northwest Forsyth Little League for many years. He was also an officer for the Pfafftown Packers in the Pop Warner Football Association. While helping the Packers he discovered his love of cooking barbeque. He and others would cook all night to sell barbeque for the Saturday home games for the organization. He cooked for baseball opening days, parties at the swim club, all the while being busy with his zoning and real estate practice. His work in zoning helped shape the city and county. He attended zoning boards, Alderman and County Commissioners meetings, and community meetings of all types. He fought for and influenced the city’s growth and how the city and county would be developed. He enjoyed work, family, and people. He hunted but rarely killed in North Carolina, Colorado, Montana and Wyoming. He rarely shot anything; his joy was being with the group. The experience of exploring, and seeing wild animals. He fished in numerous locations, even in Alaska. He Saw his children grow up and start their own families as he still enjoyed his love of law. He will miss it and all the friends he has made over the year. Ten years ago he suffered a massive heart attack, after which the Doctors said he might survive two or three months.  With sheer determination, many operations, dialysis for much of this time. He continued to fight and enjoy life. His physician fought with him and thought he was a miracle because he lived and was able to continue working in Clint’s law office. He always wanted to be a lawyer until he died.  He succeeded in that, working up to the end.  He was preceded in death by his parents. He is survived by his wife of 54 years, Jacqueline Guffey Calaway; two sons and their families, Murray (Caprina) and Clint (Jordan); Grandchildren Taleah, Treza, Toren, Lucy, Gray and Charlotte, all of  Winston-Salem; his brother Bill of Florida; and sister Sandra Hunter (Bill) of Winston-Salem. We hope you will join the family at Pfafftown Christian Church on Transou Road in Pfafftown, NC on Saturday September 22, 2018 anytime between 1:00 pm and 4:00pm. We will have barbeque, as long as it lasts, which will be cooked by Chris Pinnix on Steve’s old grill. The family wants to celebrate Steve’s life with you and your memories of Steve.

12 Responses to “Stephen Gray Calaway

  • James Clabby
    10 months ago

    We have known Steve and Jackie Calaway since 1964, during our time spent in The Army at Fort Polk, Louisiana. Without adequate housing available, we bought a trailer and resided at The Tower Trailer Park in Leesville as did Steve and Jackie. Steve was assigned to Post Headquarters, while I was assigned to a Advanced Infantry Training Company, which prepared troops for what awaited them in Vietnam. My wife, Kathy and I enjoyed many pleasant social occasions with Steve and Jackie. At the time Steve and Jackie had no children, while 2 of our 4 children, Kelly Ann and James, were born at Fort Polk. I recall a trip to Houston over a long weekend with Steve and Jackie. We returned to New Jersey when released from active duty, while Steve and Jackie returned home to Winston Salem. I recall visiting with them there during a family trip to Disney World. Much later they visited us in Westfield, New Jersey. Separated by distance, we were able to have only occasional reunions but we have stayed in touch over the years. Steve was a good friend and a kind and contemplative man. He was also a man of many interests and he will be sorely missed by many.

    Jim and Kathy Clabby
    47 Dillon Way
    Washington Crossing, PA 18977

  • Ashley and Wanny Hogewood
    10 months ago

    We will miss Steve and send our sympathy to Jackie and family. Wanny and I shared the “Deacons in Love” bond with the Calaways. Steve was our ever faithful Sigma Chi brother and we counted on being greeted with his warm smile and embrace on returns to our Wake Forest reunions. All honor to his name

  • George & Brenda Dickson
    10 months ago

    Although there never seems to be the right thing to say or do but know we are truly sorry for your loss……..with our deepest sympathy to Jackie and the family.. George and Brenda Dickson

  • Mr. Calaway was a friend, role model, mentor, and father figure to myself and too many other young men to count over the years. Such a fine man, gentlemen, and example for all to emulate. I am so fortunate and grateful to have crossed paths with him in this life. My thoughts and prayers continue to go out to the family.

  • Tom and Carolyn Clark
    11 months ago

    Although it has been many years since our paths crossed, we will always remember Steve for his generous and kind spirit. Our hearts go out to Jackie and the entire family.

  • Phillip Richard Yarbrough
    11 months ago

    I knew Steve for more than 50 years. He and my father, J R Yarbrough, were business associates and close friends. Steve was always jovial and forthright, the epitome of a man with a clear conscious.

    Steve helped me through a very trying time. Not as a lawyer; as a friend.

    I am fortunate and grateful I got to know a great man.

  • Chris Pinnix
    11 months ago

    Mr. Calaway was not only a friend, he was also a mentor, role model, and father figure for me over the 38 years that I knew him. I am sure there are countless others who feel the same way. He was a true legend that will be missed by all who were fortunate enough to cross paths with him. My thoughts and prayers are with the family.

  • Nancy S Brill
    11 months ago

    I always thought the world of Steve. He was one of a kind. I worked for the county and got to know Steve. I always enjoyed his stories. My thoughts and prayers go out to Steve’s family.

  • Anonymous
    11 months ago

    Thinking of you and your family.


  • Tim Gauss
    11 months ago

    I worked for the City-County Planning Board for several years in the 1980’s and 1990’s and had the opportunity to work with Steve on several subdivisions and rezoning requests that required approval by the Planning Board and either the Winston-Salem Board of Aldermen or the Forsyth County Board of Commissioners. Sometimes our staff position was to support his requests; sometimes we opposed the projects he represented. He was always cordial and respectful; even when we took a position against his client. He had a wry smile and a sense of humor that defused tension. He understood our respective roles and never took personal offense, nor gave any hint of animosity or resentment. He was a professional, and a gentleman. And of course there was the pipe….. I have not seen Steve for years, but I felt compelled to offer my condolences and express my gratitude at crossing his path in my walk.

  • Anonymous
    11 months ago

    I knew Steve through my daughter Dean who worked alongside Steve for 30+ years, he was a kind gentle giant who loved life and people, I personally received kindness from Steve, he will live on in the hearts and memories of his many friends. Thank you Steve for being you it was an honor to call you friend. To Jackie and the extended family who have heavy hearts I hurt with you.
    Celia Claridge

  • Dean Lusk Arnold
    11 months ago

    The world will be a little more ordinary with the passing of our unique, one of a kind special friend. Jackie, Murray. Clint and all your families, I am so sorry for your loss.

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