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Wine & Dine Wednesday event poster with "The Black Out Edition" text, hosted by Karen Vaughn with music by DJ King on July 15, 2026 from 5:30 PM to 8:30 PM at 475 Pennsylvania Street, Indianapolis.

Captain Louis Freeman holds many African-American firsts, but he will go down in history as the first black pilot to be hired by a major American commercial carrier. Capt. Freeman was hired by Southwest Airlines in 1980. He was later made the first black chief pilot of any major airline in 1992.

Capt. Freeman began making history in high school, when he and his brother were the first to integrate Woodrow Wilson High School in Austin, Texas. Upon graduation and after making more firsts in school and ROTC, Capt. Freeman enrolled in the Air Force and became the first black trainee to attend the U.S. Air Force Undergraduate Pilot Training program at Reese Air Force Base. Later, he became one of the first lieutenants to become an instructor pilot and supervisor of flying.

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