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Finding A Future Mayor in a Union Meeting: The New Adventures of Jimmy McDonough - Da Union Guy

Updated: Mar 28, 2023

By Joey McDermott

Meet James McDonough, aka “Jimmy Mac” or “Chicago” Jim. Jimmy’s a Chicago native, veteran public school educator and union activist. Jimmy’s adventures provide an insider’s view into the world of a big city union and public education. Jimmy was a field rep for the mighty Chicago Federation of Teachers (CFT) in the 2010’s. He was a founding member of the Slate Of Regular Educators (SORE) team that transformed the CFT into an agent of broader social justice and the fight for the common good.


You can follow Jimmy’s adventures in a new series written by Joey McDermott. Inspired by of our future Mayor, Brandon Johnson, Joey wrote this historical narrative/fictionalized memoir. The events and people are dramatized based upon Joey’s own personal experiences.


In Search of a Unicorn

Jimmy answered CFT President Sharon Jenkins' call as he packed his bag to leave his office.

“Hey. I hear you're going to Lewis Latimer (High School) today? Make sure you talk to the delegate - Derrell. He’s my former student. Encourage him to get more involved. We need more color around here.”


“No problem Sharon, I’ve been pushing Derrell on my end too.”


Derrell never aspired to be a delegate, let alone an activist member. He was pressured to be the delegate. His colleagues surrounded him one day and persuaded him.


“Derrell you have to do it, you’re the only teacher who’s not afraid of the principal. She likes you, she listens to you.”


The legendary Dr. Johnetta Johnson was a formidable force in the district - feared, revered and respected. The mere sound of Johnson’s stilettos caused Latimer staff to straighten up their posture. She was someone on the make - with looks, talent and ambition. Johnetta’s hard work was recognized when she later became the first CPS graduate to lead the district. Derrell knew the way to her heart and schmoozed her when the staff had issues.


Jimmy made his way to the school computer lab and the staff was already deep in discussion. Derrell greeted Jimmy outside the classroom door and whispered, “Now look! I know why you're here…Please tell my former Chemistry teacher that I’m flattered, but not interested.”


“Hold up Derrell, you haven’t even heard my rap.”


“Ok Eminem, didn’t know you could rap.”


“You know what I mean, my pitch, my appeal.”


“Tell ya what McD, I got something better for you. It’s my colleague, Brent Jackson. He’s the one you want. He’s running late, but will be here soon.”


Jimmy kept a watchful eye on the door for Brent, as teachers slowly left the computer lab one by one. After an hour it was Jimmy, Derrell and one other teacher. Derrell listened to Jimmy preach, mostly nodding and saying, “yeah, aha, sounds great. Let me know how that turns out for y’all.” He was a willing supporter, but Jimmy wasn’t going get more from him.

Brent wandered into the back of the computer lab, out of breath and disheveled, “Sorry guys, boy I tell ‘ya, I’m not in the same shape as my youth. Those baseball players kicked my butt today.”


“You’re 33 years old and act like you're 63 years old.”


“I tell ya’ Derrell, and can’t do what I used to do, but that doesn’t stop me from trying. Sorry I’m late for the union meeting, what I miss?”


Brent’s entrance brought instant energy to the room. He was a plump black man, with perpetual sweat droplets on his forehead. His fashion sense could be labeled as purposeful messiness. His hair was lined up around the edges, but unkempt on the top - a 2011 fashion pioneer, ahead of the trends. He wore hoodies with a blazer, and loose-fitting jeans. His thick rimmed black glasses revealed more of a Bohemian intellectual than an athlete. If he wore gym shoes, they were never clean air force ones, they were beat up Chucks.


Brent Jackson instantly “got it” and was up to speed on every point. Brent came from the political world and wasn’t the average classroom teacher. He understood the power dynamics of Chicago politics.


When Jimmy stated, “We need to bring back our full bargaining rights,” Brent responded, “How’s the CFT’s relationship with (Illinois Speaker of the House) Mike Madigan?”


When Jimmy stated, “We need more revenue for schools,” Brent responded, “When I worked for (State Senator) Don Harmon we always talked about a progressive income tax.”


When Jimmy stated that, “The federal government is not always a friend to public education,” Brent responded, “(US Representative) Bobby Rush…always disappoints.”


Jimmy made his final pitch to Brent and Derrell, “Be the union you seek; the union is not a vending machine, where you pay your money and receive a product. The first three letters in union?...you...and...I!” and Jimmy pointed to Brent and then at himself.


Jimmy was surprised when Brent finished the line with him by saying, “U - N - I.” Jimmy paused and waited for Brent to add more of a response.


“You’re looking at the son of an AFSCME member. I’d be disowned if I wasn’t pro-union.”


“Have you ever thought about being more involved in the union?


“Ya know….Dr. King believed in a coalition between civil rights and the forces of labor. King said the two forces united could have the greatest impact for human dignity, because their fortunes are intertwined.” Brent was also the son of a preacher; he spoke emphatically - driven by a higher power.


Jimmy smiled at Derrell, “Is this the guy you were telling me about?”


“Yes, this is Brent. Brent, this is Jimmy McDonaugh, our CFT field rep.”


“Damn Derrell! My bosses at CFT are going to lose their shit.”


“Make sure my old chemistry teacher knows it was me who made the introduction to you.”


Jimmy looked at Brent, “Do you have any plans this summer? I have a feeling my bosses are going to find a job for you, how do you feel about organizing?”


“It’s not much different than evangelizing. Social justice, equality, access to public services - it’s all the Lord's work.”


Selling the Organizer

Jimmy went straight to Mitch Baskin’s office, the CFT organizing director. Mitch kept his office dark, illuminated only by a computer monitor. Even with his thick glasses, he hunched over - inches from the screen. Mitch was deep in thought, as Public Enemy faintly played in the background. Mitch loved socially conscious hip-hop from the late 1980’s, because it “connects me to the struggle.”


“Mitch, you gotta meet this guy Brent. You’ve been saying we need diverse leaders, people who can speak for the community. Well - I found him!”


“Jimmy, I’m busy.” Mitch disdained the field reps, “If I spoke to every field rep with a story-”


Jimmy cut him off, “Mitch! Listen to me. Brent is a unicorn!”


“I’m sure he’s a nice person-”


“Mitch! You’re not hearing me. ”


“Right, Jimmy.” Mitch was suspicious of Jimmy’s intentions. “As much as I’d like to engage in one of your debates-”


“Mitch! Listen to me!” Jimmy grabbed Mitch's computer monitor and turned it sideways.


“Okayyye. That was aggressive.” He looked into Jimmy’s eyes and paused, “You have my attention. Is this guy a delegate?”


“No, but-”


Now it was Mitch interrupting, “Is he on his PPC (Professional Problems Committee)?”


“No, but-”


“How about this Jimmy, is this guy even tenured?”


“No Mitch, but I will keep bothering you until you meet him. I’m telling ya, he’s the chosen one, the messiah - whatever you want to label him. He’s the one you've been looking for.”


“OK, Jimmy, just to get you out of my office, and frankly I feel a little harassed right now, but go ahead and bring him in. Schedule an informal meet and greet, but don’t promise him anything.”


Mitch wet his pants when he met Brent. Brent said what Mitch couldn’t say. White Mitch was an only child of college professors from the University of Chicago. Brent was the son of a city government worker and a devout father of 10. Brent, as a Black man, spoke with flare, authenticity and credibility.


CFT hired Brent to work over the summer. Within months he was full time and fast-tracked to be a spokesperson, community liaison and lobbyist. Brent formed the CFT’s ministry outreach, initiated the Martin Luther King Day breakfast and was the MC for every major CFT function. Brent was a generational leader who could take CFT’s goals of social justice and common good organizing to unbelievable heights.


Jimmy believed union staff needed to do more school visits! There were hidden gems all over. Some might even make a good mayor.


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