Gregory was born in Chicago into a large and loving family of eight—six boys and two girls. He grew up in the Woodlawn neighborhood, where he attended Fiske Elementary School. Years later, he returned there as a mathematics teacher, an early reflection of the dedication, leadership, and commitment to service that would define his life.
In 1962, Gregory entered Mt. Carmel High School and quickly distinguished himself as an exceptional athlete for the Caravan. By the time he graduated, he had set the school’s career scoring record with 1,435 points—an achievement made even more remarkable as it occurred prior to the introduction of the three-point line. His single-season scoring record of 850 points stood for more than 40 years. Gregory was a starter on the 1965 Chicago City Championship team, served as team captain, and was twice named All-Catholic League. In 1966, he earned both All-State and All-American honors.
Gregory went on to receive a scholarship to Wichita State University, where he double-majored in speech and sociology while continuing his outstanding basketball career. He finished ranked eighth in career scoring with 1,545 points—a total that stood third all-time at the time of his graduation in 1970—and held the second-highest career scoring average in school history at 20.1 points per game. As a senior, he was named to the All–Missouri Valley Conference Team and earned the team’s MVP award. In 1970, he was selected to the Small Man All-American Team and drafted by the Kentucky Colonels of the ABA.
Following his basketball career, Gregory built a diverse and impactful professional life. He attended graduate school at Roosevelt University and worked as a mathematics teacher, magazine publisher, and administrator for federally funded social and economic programs. As a certified Illinois Assessing Official, he served as Deputy Assessor of Taxpayer Services for Cook County. He was also the President and Founder of the Chicagoland Sports Foundation, where he hosted a highly regarded summer basketball classic featuring several former NBA All-Stars. In every role he held, Gregory exemplified leadership, generosity, and a deep commitment to uplifting others.
Gregory’s accomplishments were recognized through numerous honors, including induction into the Mount Carmel High School Hall of Fame in 1997, the Illinois Basketball Coaches Association Hall of Fame in 2003, and the Wichita State University Hall of Fame in 2004.
After retirement, Gregory continued to give back through substitute teaching, where he was deeply loved and admired by students and colleagues alike. He spent the final ten years of his life enjoying the Arizona sun alongside his beloved wife, Annette.
Gregory is survived by his wife, Annette; his children, Staci (Eric), Gregory Jr., Kendele (Tony), and Laina (Brett); his six cherished grandchildren; and a wide circle of family and friends who will forever hold his memory close in their hearts.
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