Milwaukee County Executive David Crowley was once so gleeful about raising taxes on poor people that he celebrated by cutting a cake.
There’s a photo of it. In fact, Crowley was really proud that he took action to make it more expensive for poor people to buy a refrigerator or eat at a restaurant in his county. Of course, he’s pretending to care about affordability now and wants you to forget that his version of it was making consumer goods more expensive in Milwaukee County than anywhere else in the state.
The city/county sales tax is now among the highest in the Midwest. I learned that factoid from a flyer some PAC stuck on my doorknob. It warned me that I can’t afford David Crowley and revealed that Tom Tiffany will lower my taxes and utility bills. Tiffany gets what Tim Michels did not grasp: This election will be won or lost on pocketbook concerns and which candidate folks believe will make their lives better economically. That’s why Tiffany has been reminding people constantly that Crowley increased property taxes a bunch of times too. He also increased bus fares and salaries for executives, in case you’re counting.
I guess David Crowley made things more affordable for top executives at least.
The cake photo is that symbolic gem that captures a truth about a candidate – like John Kerry windsurfing or Michael Dukakis looking ridiculous in a tank. Crowley was proud of raising taxes on poor people when he wasn’t running for governor so why wouldn’t he raise them on you too?
Anyway, the cake photo shows Crowley with a huge gleeful smile on his face cutting the cake and celebrating the tax hike. Yes, a cliche: “Let them eat cake!” Who cares about the starving peasants when you can hobnob at the governor’s mansion with Tony Evers and Maggie Gau.
Crowley was cutting the cake with an equally gleeful County Board Chairwoman Marcelia Nicholson. Crowley literally gloated in the post about how it was time to “celebrate” the County Board jacking up the regressive sales tax that he championed and begged state legislators to allow him to do. He signed it.
Dogs in Bunny Ears

As an aside, Marcelia Nicholson is a wacky character who once toted a small dog into county meetings. And it was wearing a BUNNY costume. This provoked one of the best stories we ever wrote, which contained such gems as:
We asked Nicholson, “Why did you bring a dog with you to the committee meeting and why was it dressed as a bunny?” but received no response.
It turns out it’s not the first time Nicholson has brought her dog to a committee meeting; the meeting was about the use of goats for landscaping in county parks.
You really want the Milwaukee County experiment and mindset transplanted onto the rest of the state? C’mon.
Nicholson is a firm supporter of Crowley for governor, once blistering her fellow Democrat Mandela Barnes by angrily sniping, “Mandela entering the race just splits energy, splits support, and slows down real progress.” What’s behind the ire? Feels personal.
That’s not all. David Crowley’s greatest hits keep coming, like a bad record with a bunch of unimpressive singles.
Tampons for Boys
Crowley, it turns out, co-sponsored a bill when he was a legislator to give tampons to boys.
Specifically, the bill would require menstrual products in boys’ bathrooms. It didn’t pass, but if Democrats take control of the Legislature and Crowley wins, you’ll have to endure a lot of goofy legislation making it into law.
Want to stop it? Well, if you live in parts of West Allis, Wauwatosa and eastern Waukesha County, you can vote for reasonable moderate doctor Mike Roberts over insane liberal Robyn Vining to keep control of the state Senate in Republican hands. Otherwise, bills like this one will be dusted off and become law.
Free stuff for inmates
Democrats never met a killer they didn’t love or want to free (slight exaggeration only… Tony Evers’ first commutation board hearings are packed with them). It turns out a UW-Madison center is advocating for the release of several of the killers, but that’s another story. Since I don’t want my tax dollars going to free killers, I asked UW-Madison why this is appropriate and how much public money was wasted on this quest, but they sent back a statement that completely dodged the questions. So apparently they don’t think you should know the answer to that. Van Wanggaard has been valiantly leading the charge against freeing killers. Too bad he’s retiring.
It turns out that Democrats also enjoy giving inmates free stuff. The Milwaukee County Jail that Crowley funds gives accused killers access to free laptops and tablets.
The world learned that fact this week when a good #Milwaukee County Judge named David Borowski (yes, there is one) went off on the practice in court, inquiring “why” the Sheriff’s Department would want to give accused killers free laptops and stuff.
Fun fact: Borowski is the brother of the Milwaukee Journal Sentinel editor Greg Borowski. I could tell you some interesting stories about Greg, but I won’t, since he’s nice to and hires my students, which is great. Suffice it to say that he can be a little temperamental. He used to sit across from me in the newsroom and lose his cool when angry readers called, but he now runs the whole place, so good for him, I guess. He’s also an author and talented writer who wrote a book about Christmas and Messmer High School’s football team.
Response from a Crowley spokesperson to this story we first reported:
“The County Executive will be reaching out to the Milwaukee County Sheriff’s Office to identify any vulnerabilities in these safeguards and put solutions in place” https://t.co/gf2Vfftac1 pic.twitter.com/eXV5ysNM33
— A.J. Bayatpour (@AJBayatpour) August 29, 2026
Anyway, David is temperamental too – about all of the right things. He is the best Milwaukee County judge. He routinely calls out criminals and actually puts them away and stuff, you know in contrast to all of the squishy bleeding heart public defenders Evers has placed on the bench throughout #Wisconsin, a practice Crowley would surely continue.
David Borowski is also a good quote. He delivers, as they say in journalism, a “money quote.”
“Why is the Sheriff’s Department giving laptops and iPads to defendants that are charged in homicides or any defendant?” David asked, in a video posted by fair television reporter AJ Bayatpour.
David then ticked off a number of horror stories stemming from this ridiculous practice, including a defendant accused of using the provided laptop to intimidate witnesses and watch child p*rnogr*phy. He said another defendant in a different court was accused of making 1,200 attempts to intimidate from a tablet. He then pointed out that the defendant in front of him this week was accused of a triple homicide and also allegedly using a laptop to discuss threatening witnesses. He called the whole thing preposterous because it is.
Crowley, it turns out, signed off on a vendor contract to allow this. Of course.
The jail that Crowley funds also refuses to call inmates “inmates,” by the way, calling them “occupants” instead. The website says, “Occupants can only make outgoing calls. No incoming calls are allowed.”
And they say August is a boring month in politics! Just wait until after Labor Day. That’s when things really rock and roll.
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