Who Is Reggie Jackson?

by Dan O’Keefe

To some, the name Reggie Jackson brings up the image of a celebrated New York Yankee home run hitter. Milwaukee’s Reggie Jackson, however, is a bookish fellow with thick glasses who reads, writes, and gives talks. He talks to us about our own neighborhoods, our parents, grandparents and all those who came before. In other words, he talks about our history, and about its most difficult part: the continuing legacy of racism.


Reggie applies the skill of a public historian, one who takes history off dusty shelves and shows how those stories still live among us. His column in the Milwaukee Independent (milwaukeeindependent.com) illustrates his skills. He brings together current events, the history of the relevant parts of that event and shows how they intersect with racism. In a recent column, about the blackface incidents in Virginia and a high school in Port Washington, Wisconsin, Reggie described how blackface began in the 1830s or 1840s, and explained that, while the news about this is new to some, this behavior became and remains part of our social fabric. The fact that a medical college would allow photos of students in blackface to appear in its yearbook, and that students at a high school would engage in blackface jeering, substantiates the continued acceptance of this toxic, racist behavior by parts of our society.

Reggie’s columns are clear and easy to read. He writes with an indisputable logic which is enhanced with a storyteller’s clarity. The tone of his columns is much like his talks, one fact after another and delivered with emphatic urgency. While neither his column nor his talks are delivered in anger, one is compelled to read his complete column and hear out his speech.


As a speaker, Reggie attracts a significant audience. He has given his talk on the continuing cost of segregation in Milwaukee nearly eighty times. When discussing the long history of Milwaukee’s segregation, he informs listeners of the prevalence of restrictive covenants in metropolitan and suburban Milwaukee. He describes the open housing marches and shows how the so-called success of open housing ordinances in the city is false. His statistics demonstrate how those past actions, as well as many others, still weigh heavily even now. He adapts his talks to his many types of audiences including churches, libraries, businesses, non-profits, schools and universities.

He is developing a new talk called, “The 2.2 Million: The History and Human Cost of Mass Incarceration.” Reggie offers a new way of looking at mass incarceration. This complex topic will be covered by Reggie in several segments. He describes how the American criminal justice system is not a unified criminal system at all. Each county or its equivalent is its own system totaling more than 3,000 systems. He wants to also explain that the reason we can’t reduce the prison population is because of the huge number of jobs depending on incarceration: lawyers, court clerks, parole officers, probation