Back in middle school, I always got picked last in kickball. It was mortifying. And when I tried to play middle school basketball, the coach laughed at me because I flinched when someone threw me the ball. I went on to become an all-conference volleyball player anyway by practicing my serve over and over again by myself behind my rural home up north (great life lesson; never give up), but I never forgot how it felt to stand in a line while everyone else was chosen.

So I relate to how Democrat governor candidate Joel Brennan must be feeling. The dude is constantly being picked last in the Democratic kickball primary even though he’s unquestionably the Democrats’ best candidate for a general election. When I saw a photo of Brennan looking forlorn while Mandela Barnes blathered away next to him, I almost wanted to give him a plate of cookies, a glass of Tom Tiffany’s whole milk, and wrap him in Virgal’s quilt, to make it all go away. But not really. Likely Brennan thought bubble: “How is this clown ahead of me? Does he even have a job?”

Joel, get with the program. Maybe if you start jumping around in a weird jumpsuit ranting about capitalism, and abolishing the MPD, private property, and the U.S. Senate, you’d have a chance in the Democrat primary. Quick, find an America-hating podcast to go on! Actually, don’t. But it’s a sad statement about the state of your party that a guy like you can’t get any attention. The Democratic Party’s fulcrum used to be unions. Now it’s anyone’s bet. The inmates are running the asylum. But what’s surprising is that, even in this war between the establishment and the socialists, you’re not the go-to guy of the former.

It’s hard not to be picked, and this guy just can’t get any love from his Democrat family. He’s like the responsible overlooked sibling who gets a 4.0 and goes to college but sits woefully ignored while the parents gush over the flashier sibling who dashed in late, lives in the basement, smokes too much weed, and ran over grandma in the parking lot.

Even when Brennan unusually released a lengthy oppo book on himself, no one cared. “Over here! Hey, I’m over here!” it screamed. He even made a cryptic reference to Democrat candidates having “skeletons” in their closets but all anyone wants to write about is Francesca Hong hoping to abolish the police (which is insane).

The stakes in this election are too high to just hope we don’t have any “October surprises” — voters deserve to know who they are putting up against Tom Tiffany and what skeletons might be living in each of our closets. So today I’m releasing 99 pages of opposition research on… pic.twitter.com/iFeh1QwZ5Q

— Joel Brennan (@joeltbrennan) July 7, 2026

I read Brennan’s oppo book on himself so you don’t have to (I was likely one of five readers, all reporters), although no one believes that, if Brennan has any actual skeletons, they would make this document. It does clarify that Joel Brennan is not insane, though, which is why he’s not breaking through.

We learn about such minor league dirt as, “In April 2008, the city of Milwaukee assessed an unspecified permit violation which was remediated within two weeks with no fees assessed” at Brennan’s humble $468,000 house. There’s even a picture of it! He lost a state senate race and voted to raise the food and beverage tax in Milwaukee. We also learn that he was “praised” by the Milwaukee Journal Sentinel. Hey, Joel, most oppo books don’t gush about the candidate.

The book is Brennan’s desperate bid TO JUST BE TALKED ABOUT (hey, Joel, it worked!)

Lt. Gov. Sara Rodriguez’s entire claim to being a “moderate” is living in Waukesha County, yet she’s the one powerbrokers are rallying around. She hasn’t done anything. Even Tony Evers can’t stand her. Poor Joel Brennan.

Scott Fitzgerald Likes Joel Brennan!

Brennan, we learn, was actually praised by arch Republican Scott Fitzgerald, who once declared that Brennan was a “great guy.” He opposed that crazy MPS referendum. He helped bring the RNC to Milwaukee. He doesn’t want to totally abolish ICE! His org commissioned a study on police short staffing! On the other hand, he donated money to Brad Pfaff and wants to free a bunch of prison inmates.

To be honest, all of this stuff is another reason why Brennan is the Democrats’ best candidate – and why he’ll never get through a primary increasingly dominated by anti-capitalist America-hating nut jobs.

The Democratic Party of Wisconsin is in a fight for its very soul. And losing.

Brennan’s “oppo book” also takes great pains to remind people that his brother-in-law is businessman Kevin Conroy probably because Conroy is ungodly rich (over $200 million by some accounts.) The Conroy angle has floated around for months usually combined with speculation that he could toss some cash in to boost Brennan’s bid.

Will Joel Brennan Quit?

The scuttlebutt all weekend among the political class is that Brennan will soon quit. No one thinks political jellyfish Brennan has the spine to stand against Democrat establishment pressure to clear the decks for Rodriguez in the hopes she can defeat upstarts Hong and Barnes (although what can they offer him? He’s already been DOA secretary). The parlor game debate centers only on when he will quit. Before the Marquette poll to save face when he comes in at 1% again? (It comes out Tuesday.) After the Marquette poll in case he somehow doesn’t? Or is he waiting for campaign finance reports to come out in a few days with a big surprise?

Joel wasn’t giving up this weekend, though. He posed gamely in front of a hodag, driving all the way to Rhinelander, and no one gave a sh*t. He praised David Crowley when the Milwaukee County exec quit, and Crowley returned the favor by endorsing a privileged woman from Waukesha (Rodriguez) who has done literally nothing, is rude, and who took utility PAC donations after voting for a utility tax loophole (while your rates go up).

I’m told by a couple people who know Brennan that he can be lazy and insincere, saying what people want to hear, and they’re not Republicans. That being said, his resume swamps the rest of the Democratic Party field.

He ran Discovery World in Milwaukee and was president of the Greater Milwaukee Committee. That’s a major business group. He was the Secretary of the Department of Administration for Gov. Tony Evers. He worked for Miller Brewing. He helped Tom Barrett’s campaigns. He served on the Wisconsin Center District Board. He helped spearhead major negotiations for the state.

Sara Rodriguez? She worked as a nurse, did nothing in the state Assembly for a couple years and then did nothing as lieutenant governor. The establishment picking her is like affirmative action for the privileged white Karen from the ‘burbs.
So why can’t Joel get any love? Here are my best theories.

He’s a White Guy

Brennan is a white guy in an identity politics obsessed party. Down with the patriarchy!

He Looks ‘Corporate’

Brennan, with his glasses and neatly pressed suit and blue dress shirt, looks too corporate in a party that increasingly hates capitalism. His opponents run around in rainbow shawls and painter’s coveralls. Plus, the GMC is boosted by corporations! Down with capitalism!

His Photos Suck

I’ve met Joel Brennan. He made a beeline for me at a Democrat forum, recognized me, praised my work with journalism students, and revealed a charming anecdote about his parents before a frazzled campaign operative whisked him away. I appreciated this sign of respect and willingness to engage across the aisle.

But I almost didn’t recognize him. He looks better in person. His photos make it look like he weighs 75 pounds more than he does. I know it’s a small point. But get a better photographer Joel because I heard a top Democrat making the same point. Your pics don’t do you justice. Stop shooting upward angles.

Tom Barrett

Brennan is former Milwaukee Mayor Barrett’s godson, and he worked for him. Maybe people don’t like Tom Barrett. He wasn’t exactly a great candidate for governor himself. Brennan is basically a Barrett franchisee.

Not Doing Anything to Stand Out

Brennan has been running a milquetoast campaign. He’s done nothing to stand out, the oppo book stunt aside. He could find his inner conscience and strongly speak out against the craziness in his own party.

This is not asking too much. All he has to do is vocally, and loudly, defend capitalism and make it clear that antisemitism, abolishing the police, abolishing the U.S. Senate, going on the podcast of someone who thinks we deserved 9/11, and abolishing the prison system are wrong.

Instead, he’s stayed silent and run like a lemming to the far regions of the left like the rest of them. Brennan should stop chasing Hong and make a bold statement about the soul of his party. There are a lot of moderates who don’t know what to do. Instead, he’s being crushed in the middle of the radical mosh pit. Joel: you’re never going to out Hong Hong. It sounds really stupid and phony when you (and Kelda Roys) try to do it.

Free advice: Find your damn conscience and speak it.

The Polls

Democrat establishment elites are desperate to defeat Hong and Barnes, who are consistently the top two in polls. Rodriguez consistently places third. She’s behind but the only Dem in striking distance. At some point, the polls become a self-fulfilling prophecy.

When Brennan inevitably quits, voters will say “Joel we hardly knew ya.” But there will be buyer’s remorse someday. Rodriguez excites no one. If Hong gets through, Tiffany will likely win, and if he doesn’t somehow, she will destroy the state, so Republicans will win it all back in four years then anyway.