Cover photo for J.D. Callaway's Obituary
J.D. Callaway Profile Photo

J.D. Callaway

February 10, 1936 — June 4, 2023

Bay St. Louis

J.D. Callaway

Jimmie Darrell “JD” Callaway, age 87, of Bay St. Louis, MS, passed away on June 4, 2023, in Bay St. Louis.

He was preceded in death by his father, James Callaway; his mother, Naomi Callaway; and 2 sisters, Lynn Hula and Kay Boe.

Mr. Callaway is survived by his loving wife of 62 years, Kay Pearl Callaway, his daughters: Jamie Lynn Skladzien and Anne Callaway, a sister: Yvetta Iverson (Toby), & 4 grandchildren: Christopher Skladzien, Suzuane Skladzien, David Skladzien, and Kaylynn Lamar; his amazing nieces and nephews to whom he always brought fun treasures to, and all of his wonderful in-laws whose lives he brightened along the way.

J.D. was born on the family farm in Quinlan, Oklahoma where he was raised with his three sisters. During his high school years the family moved to Presho, South Dakota. While in his new high school, JD played football and basketball and would later come to enjoy hunting with his father-in-law. It was here in this small farming town he was to meet his wife, Kay Brakke; and although she knew it the first time they met (just ask her), it wouldn’t be until after they spent a few summers working together at the local diner JD helped Melvin Hutchinson build and operate (Hutch’s Café) that they would come to marry at the end of winter in 1961.

A couple years into their marriage they would welcome their first daughter, Jamie Lynn, into the world. Following his ever present entrepreneurial spirit the young family packed up in the late winter of ’64 (in what I can only imagine was a covered wagon) and headed out west in search of prosperity and self-actualization.

Wickenburg, Arizona is where they would settle and using  his new-found knowledge and skill-set went on to open the Sun Dial Café nearby in Carefree. It wouldn’t be long after celebrating the birth of their second daughter however, sensing the shifting winds of opportunity, JD would seek to strike his fortune in the new construction of the electrical pylons connecting the southwest that stand in operation to this day.

Following in what now has become a characteristic of his, JD attained his contracting license and went back to work for himself applying his construction experience by building homes for individuals in the surrounding neighborhoods. While he successfully built quality homes that last to this day; in 1977 JD and his family would once again move across the country to a small and up and coming town outside Houston, Texas called Katy

Following his entrepreneurial spirit it would be here in Texas that he would spend a good part of the rest of his working years. Starting with a CDL and one truck, JD and Kay would grow CalCarCo, Inc  by the year 2000  into a fleet of 8 trucks and employing several drivers hauling cars across the entire continental US. Following the recession JD and Kay found themselves down to one truck but happily logging the books together with their chocolate poodle companion “Chocers.” After taking advantage of this slower pace to spend extended time with the many friends and family he and Kay both had meet and come to know across the decades. In 2013 JD sold his custom made Peterbilt that he had to come to clock over 3 million miles on and in 2018 retired to the beach community of Bay Saint Louis to be in the company of his ever loving wife, his daughter, and grandchildren.

If there is one thing we should all take away from the life of JD Callaway: his rugged individualism and relentless pursuit of the American Dream. His resilience and determination to provide a better life for him and his family off the sweat of his own back, the ingenuity of his intellect, and the providence of foresight. The man built and lost enough fortunes for several men, but through it all kept a heart full of joy and love for those blessed enough to know him.

The family will hold a private celebration of his life at a later date.

The Riemann Family Funeral Home, 141 Hwy 90, Waveland, is serving the family and online condolences may be offered at

To order memorial trees or send flowers to the family in memory of J.D. Callaway, please visit our flower store.


Visits: 595

This site is protected by reCAPTCHA and the
Google Privacy Policy and Terms of Service apply.

Service map data © OpenStreetMap contributors

Send Flowers

Send Flowers

Plant A Tree

Plant A Tree