Maze Jackson

Last night, for the first time since Election Night, March 15, 2016 I attended a Democratic fundraiser. While I have not been in hiding, as some would like to think, I had avoided attending some high-profile events because as a true Chicago political operative, I knew it was coming…the jokes about 68%-32% drubbing that my good friend Ken Dunkin received. I knew I would be the target of the jokes, because as many felt, rightfully so, that I had worked for Dunkin behind the scenes.

Dunkin was ultimately crushed by the sheer weight of the entire Democratic Party putting every available resource against him, but he did not go down without a fight. And when he was given the resources, party leaders were clearly concerned that Dunkin could still win the election, so concerned that they even called in the leader of the free world. That’s right, even President Obama weighed in on the election, at which point I faced the reality that the Democratic Party was willing to do ANYTHING to ensure Dunkin’s defeat. It was a tough loss and I knew they would come for me afterwards.

But walking into that fundraiser and hearing fellow Black political operatives laugh about how they “Kicked my butt!” stung a little. Then when a committeeman that I have known, supported, and respected shouted out in front of a table of strangers, “WE KICKED YOUR ASS!” it stung A LOT. It stung because so many times, I had been on the other side, laughing at those idealistic political wannabees, whose hopes we laughed at, as we mercilessly kicked their butts at the ballot.

It stung because as a Black political operative, I know that there are two different “WE’s.” As a Democratic political operative any win against the opposition is cause for celebration. But “WE” for Black Democratic political operatives usually means working as the “field” director, while inexperienced young White Democratic political operatives handle jobs like media director, communications director, campaign manager, and fundraiser.


“WE” to Black Democratic political operatives means that you get a small raise or promotion, while White Democratic political operatives get lucrative contracts or new business clients. “WE” to Black Democratic political operatives means a win bonus that may pay for a weekend in Wisconsin, while it means buying a vacation home in Michigan for a White Democratic political operative.

I was content being a Black Democratic political operative until I went to Springfield and saw what it meant to be a White Democratic political operative. I saw all of those young twenty and thirty something hustling around the Capitol in their fancy suits, with big contracts, representing corporate America working 3 days a week, six months per year. I saw them taking multiple family vacations, living in big houses in (847) area codes, and driving fancy cars on the weekend. Their outcomes looked nothing like those of the Black Democratic political operatives I know.


The top Black Democratic political operatives I know are the people behind the desks at your local ward office. You may see them walking around city hall, or they may be sitting in the back of the room at your local block club meeting. They know what to do, who to talk to, and where to be in their communities. Black political operatives are experts in their communities. It’s generally who the White Democratic political operatives rely on for success when they are dispatched to Black communities.

But few if none of them will ever be millionaires like the White Democratic political operatives that they work along side during election season. As a political operative, I understand that when the boss sends you on a mission, your only goals are to destroy the competition and win. But as a Black Democratic political operative, I know we are rarely if ever allowed to control the budgets, make decisions, or be part of the strategy team. They will let us handle the “ground game” and “visibility” which is cool, but we won’t ever retire millionaires like the White Democratic political operatives.


Going against the Party in the Dunkin race may not have been the smartest thing for my political or professional career, and I admit that. I’ll even admit I did get my butt kicked. But while that Black Democratic political operative was at the same event with me on a cold dreary March night, laughing, the White Democratic political operative that needed him to win, was chilling on a beach with his family. When I reminded him of that,  things weren’t so Democratic or funny anymore.