This writer has lived in Milwaukee County her entire life, but she's worked and spent plenty of time outside of the county. One thing remains true: Wisconsin residents who live in the 71 other counties despise Milwaukee. They see it as a giant vacuum that sucks up our tax dollars, is riddled with crime and violence, and runs roughshod over the rest of the state.
They're not wrong.
Milwaukee County Executive David Crowley has made things worse. Taxes have gone up under his watch, and he even celebrated raising the county sales tax rate by eating cake. The Milwaukee County Sheriff's office is chronically understaffed, and the county is running a massive budget deficit.
Despite all of that, Democrats said Crowley was their guy and he's their nominee for governor.
But Crowley's Republican opponent, Tom Tiffany, just dropped an ad by a guy who has lived in Milwaukee for almost five decades, and the message is clear: David Crowley is not good for Wisconsin.
🚨NEW AD: Jim, a Milwaukee County resident of 46 years, says @DavidCCrowley has got to go.
— Tom Tiffany (@TomTiffanyWI) September 15, 2026
"I've seen crime rise, my property taxes rise, and my overall services go down. My sales tax almost doubled... David Crowley had his chance. We can't afford him to be up in Madison." pic.twitter.com/lfNXYhbi9R
"I've lived in Milwaukee County now for 46 years, I've seen politicians come and I've seen them go. And I'll tell you right now: David Crowley's got to go. I've seen crime rise, property taxes rise, and my overall services go down," Jim said.
"My sales tax almost doubled," he continued. "Obviously, our streets haven't improved, and obviously the affordability of homes and everything else has not increased. David Crowley had his chance. We can't afford him to be up in Madison. David Crowley is a failed county executive and he'd be a failed governor."
Very strong ad for Tiffany. The historic notion, backed by results, is that Milwaukee politicians usually fail to do well statewide, in recent decades. Hopefully this hits hard and lets us run up the score in the suburbs. https://t.co/s68TjvKtnX
— Wisconsin’s Conservative Sponge (@wiz_political) September 15, 2026
Milwaukee politicians do fail to do well statewide, by and large. Democrat Tom Barrett, former Milwaukee Mayor, failed multiple times to win the governorship.
Scott Walker won because he came in and cleaned up the mess in Milwaukee County left by Democrat Tom Ament.
This is exactly correct.
— Andrew Moser (@Andrew_Moser) September 16, 2026
I have met and genuinely like David Crowley as a person. I think he’s a good man.
But I know he’s not up to the task of governing our state. His body of work unfortunately makes it clear. https://t.co/zNhRsM2bhK
Crowley's record is clear: high taxes, more crime, fewer services. He'd do the same thing in Madison, and Wisconsin cannot afford that.
Editor’s Note: The 2026 Midterms will determine the fate of President Trump’s America First agenda. Republicans must maintain control of both chambers of Congress.
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