On Episode 41 of Rich Lessons, Sevetri Wilson Taylor (Instagram.com/sevetriwilson) and Sheena Allen(Instagram.com/whoisSheena) talk with Karen Freeman-Wilson, former Indiana Attorney General, the first Black woman mayor of Gary, Indiana, and now President & CEO of the Chicago Urban League.
Karen opens up about growing up in Gary’s industrial heyday, witnessing its economic collapse, and leading through a $26 million budget loss on her first day as mayor. She breaks down the realities of running a predominantly Black city, confronting systemic bias, and rebuilding trust between citizens and government.
From redirecting Indiana’s tobacco settlement funds entirely to health initiatives to reshaping Chicago’s community narrative, Karen shares how leadership grounded in empathy and accountability can change outcomes. The conversation dives into today’s political climate, the quiet rollback of DEI, and her warning against what she calls “legislative genocide.”
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Show Notes:
(00:00) Intro & welcome
(01:18) Mini bio & firsts (AG; first Black woman mayor; now CUL CEO)
(02:47) Gary’s boom → decline snapshot
(04:44) Bias toward Black-majority cities explained
(07:12) Day-one $26M budget hit; “expect more” leadership
(11:06) AG wins: nursing homes reform; 100% tobacco funds → health
(14:17) Harvard story: grit & “finish what you start”
(18:30) Loss → Chicago Urban League; narrative + cross-sector work
(22:49) “Show up twice”: block + boardroom approach
(25:32) Today’s climate: values, DEI retreat, bill impacts (SNAP, schools, health, environment)
(33:19) Nonprofit response; job fair surge (3K in-person / 5K online)
(41:01) Rich Lesson: treat people how you want to be treated
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Rich Lessons Podcast // hosted by Sevetri Wilson Taylor and Sheena Allen
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