Derrick Freeman Jackson

Derrick Freeman Jackson, 73, died Sunday, September 29, 2024, in Mission Viejo, California, after a brief illness.

Derrick was born on March 18, 1951, in Chicago, Illinois, to Beatrice and Robert Jackson, the second of their eight children. Derrick grew up on the city’s South Side, where he had a daily paper route, spent summers playing baseball with friends, and developed his lifelong love for Jackie Robinson’s Dodgers. He attended Harlan High School and proudly wore his letterman’s jacket with the varsity letters he earned for achievement on the track team in sprinting and pole vaulting, an event in which few African Americans competed. To quote a childhood friend, “He was tough, dedicated–and he was a winner.”

Years later, Derrick’s alma mater recognized him for his positive impact on the community through good deeds, strong character, and professional accomplishment by inducting him into the Harlan High School Hall of Fame.

Throughout his life, Derrick embodied the integrity, honor, and grit his father demanded of his eldest son. These values carried Derrick through life’s challenges and, coupled with his mother’s attentive kindness and acceptance, fostered his keen perception of human behavior. Ever vigilant, he kept his eyes and ears open, stood firm in his beliefs, and lived an upright life of service to the Chicago community, armed with the wisdom to know when to be cynical and when to show compassion. Those who knew him often sought his wise counsel to talk through issues, analyze problems, read over complex documents–he was an excellent proofreader–and, most valuably, offer them thoughtful solutions.

Derrick attended Western Illinois University on an athletic scholarship and earned a Bachelor’s degree in education. He also played football, worked for the athletic department as a student trainer, and joined the Black Student Association. He returned to Chicago and taught physical education at Scott Elementary. Never a social butterfly, he and his close friends enjoyed going to see live jazz and having serious conversations over late-night pizzas.

In 1978, after teaching for six years in Chicago Public Schools, Derrick left education to become a firefighter. His 32-year career with the Chicago Fire Department fueled his professional, social, and intellectual world. He served the citizens of the City of Chicago in both operational and administrative capacities and earned a Master’s degree in Public Administration from Roosevelt University in 1991.

Derrick’s first assignment was at Engine 13 downtown. He later worked at Truck 11, one of the busiest truck companies in the United States. He joined the department at a time when there were few minority firefighters, and the adversity he faced and endured informed his resolve as a manager to command respect for himself and demand it for others.

Derrick possessed profound institutional and historical knowledge and cultivated deep relationships with his colleagues while rising through the ranks from engineer to lieutenant, captain, battalion chief, and into management. His work overseeing labor relations as Director of Employee Relations reflected his respect and concern for his fellow firefighters and paramedics, and he worked hard to ensure the racial makeup of the fire department mirrored Chicago’s diverse population. He was appointed Deputy Fire Commissioner of Administrative Services in 1999 and became President of the Firemen's Annuity and Benefit Fund. In these roles, Derrick earned his colleagues’ respect as a man of his word, a tough negotiator, and a deliberate decision maker. Throughout his time at the Chicago Fire Department, Derrick developed friendships that endured until the end of his life.

Derrick retired in 2010, and he and his longtime love Jennifer Ross married in 2020. They eagerly traded Chicago’s snow for California’s sunshine, yet Derrick remained a loyal Chicago sports fan and missed his favorite Chicago foods: Harold’s Chicken, Al’s Beef, Maxwell Street Hot Dogs, and Lem’s Bar-B-Q. He followed the White Sox and loved his Chicago Bears yet gladly cheered once again for his Dodgers, now his home team.

In retirement, Derrick’s greatest passion was golf. He frequented his favorite local course, fittingly, Chicago’s Jackson Park, and he and his new neighbors in California golfed at least twice a week. He also enjoyed monthly poker nights with “the guys.” Derrick felt great pride that his daughter Christina followed in his footsteps as a Chicago firefighter and enjoyed their long conversations. He loved traveling with his wife Jennifer, tending their garden, rewatching old Westerns, learning and talking about history, and sharing stories about his rich life experiences. He thought constantly about his loved ones and how best to keep them safe. That dedication and protective spirit will be missed by all, as will his passion, curiosity, hearty laugh, good heart, and 1000-watt smile.

Derrick is survived by his beloved wife Jennifer Ross; his treasured daughter from a previous marriage Christina Jackson; his step-children Jacob Shapiro and Ma’or Shapiro; his siblings Carmen Cannon, Yolanda (Andrew) Oliver, Barbara Thames, Jennifer Jackson, Gail Jackson, and Robert (Magalie) Jackson, Jr.; his sister-in-law Rebecca Ross; his nieces and nephews Lindsay Fletcher Weiss, Brandon Wilson, Samuel Morgan, Andrew Oliver, Patrick Oliver, Justin Jackson, Valencia Jackson, Bobby Jackson, Breyon Jackson, Cortel Jackson, Linda Jackson, Sabrina Ross, and Gabriel Ross; and his lifelong friends Timothy Hart and Larry Lewis.

Derrick was preceded in death by his parents Beatrice and Robert Jackson, his sister Sheryl Jackson, and his brother-in-law Robert Thames.

In lieu of flowers, donations may be made to 100 Black Men of North Metro Atlanta, Inc . Derrick actively supported its mission to increase opportunities for African American youth through education and economic mentoring.

The family would like to extend special thanks to the doctors and nurses at Providence Mission Hospital.

A private memorial service will be held in Orange County, California.