Missouri Democratic Rep. Bill Clay Sr., the first black congressman from the state, died on Thursday after serving 32 years in the U.S. House. He was 94.

Clay, a civil and workers’ rights advocate, represented the state’s 1st district from 1969 to 2001, and he was a driving influence in St. Louis’ recovery after “white flight” following the Civil Rights Act. He bartered with construction trades and corporate C-suites to see his hometown transformed into the skyline that now surrounds its iconic arch.

Prominent Democrats’ endorsements had a significant impact on the election prospects of fellow party members, and he was known for demanding unwavering loyalty from those who gained his approval.

“The Black community, almost overwhelmingly, looked at him as a fighter for them,” said his son, former Congressman Lacy Clay (D-MO).

In the years after the enactment of the 1965 Civil Rights Act, black St. Louisans moved quickly to capture power in a city that had long separated its communities via historically discriminatory redlining policies. Clay, Sr. was ahead of his time, gaining his first election to the St. Louis Board of Aldermen in 1959 at the age of only 28.

He became a staple during sit-ins as members of St. Louis’ black community protested the segregation enforced by businesses such as White Castle and Howard Johnson, which divided black and white customers into separate seats and hotel rooms.

“St. Louis was no different from any of the cities in the South,” Clay said in a 1998 profile. “We had rigid segregation — not by law, but by custom.”