151. Revisiting Race Relations: Letters in Black and White with Winkfield Twyman & Jennifer Richmond

The co-authors of "Letters in Black and White" found common ground in their frustration with America's polarized racial discourse. Our conversation explored provocative ideas like "Blackness as oppression"—a concept that shook Wink's foundational beliefs about identity—and Jen's jarring return to an America where diversity training often stifled genuine dialogue.

We challenged simplistic narratives of "privilege," examined the controversial topic of reparations (with Wink offering a compelling case for Black agency over victimhood), and questioned how society's racial scripts influence our thinking. Throughout our discussion, we highlighted the power of curiosity and personal storytelling to bridge seemingly insurmountable divides—inviting listeners to reconsider their own perspectives on race and identity in America.

Winkfield Twyman and Jennifer Richmond are co-authors of Letters in Black and White: A New Correspondence on Race in America.

A former law professor and current author, Winkfield (Wink) Franklin Twyman, Jr. is a southern writer from a small-town suburb outside of Richmond, Virginia. Wink lived on Twyman Road until the age of eight. Everyone on Twyman Road was a Twyman. A graduate of the University of Virginia and Harvard Law School, Wink has penned articles and essays in the South Carolina Law Review, the Virginia Tax Review, the National Black Law Journal, the St. Croix Review, the Pennsylvania Law Review, the Intellectual Conservative, The Civil War in Pennsylvania: The African American Experience, the Richmond Times Dispatch, the Chicago Tribune, and the New York Post. Wink identifies as an American Native to Virginia. Follow him on Substack or his personal or professional Facebook page.

A former professor at Trinity University on Chinese Politics and Vice President of International Projects for Stratford, Jennifer Richmond now serves as the Executive Director and Co-founder of the Institute for Liberal Values. In this role, she takes her academic acumen and knowledge of authoritarian governments, turning her attention and skills towards the most polarizing issues within the United States.

Instagram: @jsrichmond @ilvalues

X: @truth_inbetween @ilvalues

LinkedIn

YouTube: @ilvalues

00:00 Start

[00:02:09] Polarization in race discourse.

[00:03:55] Diversity training experiences and reflections.

[00:10:11] Language and cultural privilege.

[00:12:59] Individuality vs. Stereotypes in Society.

[00:19:20] Black identity and entrepreneurship.

[00:20:58] Fatherlessness and its impact.

[00:25:35] Racial solidarity and misalignment.

[00:29:54] Individuality in racial narratives.

[00:32:48] Kafka traps in wokeness.

[00:37:27] Opposition to reparations for slavery.

[00:40:14] Reparations and black agency.

[00:45:43] Post-traumatic growth syndrome.

[00:49:04] Family personality and resilience.

[00:52:49] Curiosity and cognitive ability.

[00:58:23] Slavery in Family Genealogy.

[01:00:49] Ancestry and racial identity.

[01:04:32] Ghost slaves and modern comforts.

[01:09:05] Perspective taking and arrogance.

[01:11:56] Lack of empathy in communication.

[01:16:22] Racial consciousness in family dynamics.

[01:20:44] Fragmented identity and cultural expression.

[01:25:50] Racial identity and cultural upbringing.<