Crowley, Tiffany Launch Dueling Seven-Figure Ad Blitz For Governor

Milwaukee County Executive David Crowley (left) and U.S. Rep Tom Tiffany (right). Angela Major/WPR

The hot takes and “what-ifs” about Democrats’ chaotic primary for governor are still swirling, but the general election ad war has already begun.

A day after Milwaukee County Executive David Crowley’s impressive, but improbable defeat of Madison state Rep. Francesca Hong, U.S. Rep. Tom Tiffany’s campaign announced it launched “seven-figure” statewide ad campaign attempting to paint the Democrat as a “failed executive” of Wisconsin’s most populous county.

“David Crowley spent recklessly, botched health insurance for thousands, raised property and sales taxes,” said the 30 second ad’s narrator in the ad titled “Geez, That’s Crazy.”

The ad also alludes to Crowley’s primary campaign against Hong, a democratic socialist.

“Even David Crowley says there’s no real difference between him and socialists,” said the ad’s narrator

The same day, the Democratic Governors Association announced its own “seven figure statewide buy” with an ad titled “Pander.” The 30-second spot shows clips from Tiffany campaign commercials as the words “PANDERING POLITICIAN” fill the screen.

“Pandering politician Tom Tiffany pretends he’s anything but a congressman with a MAGA agenda,” the narrator claims. “The truth? Tiffany’s agenda is so radical that even Republicans say he’s part of a group of legislative terrorists in Congress.”

The ad also claims Tiffany “supported Jan. 6 rioters, voted to slash Social Security services and co-sponsored a bill to ban abortion with no exceptions for rape or incest.”

It’s all par for the course as Democrats and Republicans race to define their opponent in the governor’s race. University of Wisconsin-La Crosse political science professor Anthony Chergosky says Tiffany’s campaign is “under a lot of pressure to urgently define Crowley.”

Chergosky said the 2022 election when Republican U.S. Sen. Ron Johnson defeated Democratic challenger Mandela Barnes is an example of why that’s so important. Chergosky said Barnes was “caught flat-footed” by a barrage of negative ads, and he had to spend the rest of his campaign trying to recover.

“That’s the risk for a candidate when they don’t have a well-defined political brand, and they’re still working to introduce themselves to the electorate,” said Chergosky.

Republican U.S. Rep. Tom Tiffany addresses reporters at the Rustic Manor 1848 wedding barn in Hartford Tuesday, Aug. 11, 2026, after winning the GOP primary for governor. Rich Kremer/WPR

Tiffany’s new ad is also a bit of a forced pivot for Republicans, as third-party groups backed by the Republican Governors Association spent millions of dollars on ads focused on Hong, which Democrats claimed were aimed at trying to help her win the primary. Since Crowley’s win, some Republicans have questioned whether the GOP should have waited to attack Hong until after she was the Democratic nominee.

Chergosky said he thinks the RGA ads were “too cute,” because they tipped the Republican Party’s hand. He said that ad campaign, along with a big surge of TV ad spending by Crowley’s campaign in the final days of the primary, “is evidence that television advertising still matters a lot.”

Democratic candidate for governor Milwaukee County Executive David Crowley speaks at a rally Wednesday, Aug. 12, 2026, at the Racine County Democratic Party Office in Racine, Wis. Angela Major/WPR

Buying TV time is expensive, and Tiffany’s campaign has had no trouble raising the cash to dominate Wisconsin’s airwaves, thus far. At the end of July, Tiffany reported having nearly $5 million in cash. Much of his fundraising has come from billionaire Republican megadonors Richard and Elizabeth Uihlein, along with Diane Hendricks.

Since he relaunched his campaign with the backing of Democratic Gov. Tony Evers, Crowley’s fundraising has surged. His campaign claims he raised more than $1 million in the first 24 hours after his primary win.

Sabato’s Crystal Ball, which is part of the Center for Politics at the University of Virginia, has shifted the race from “Toss-up” to “Leans Democratic” with Crowley’s victory. Chergosky said if Republican donors start having concerns about Tiffany’s ability to beat Crowley, “they might want to surge their resources elsewhere.”

“To the extent that Republican megadonors believe that Tiffany has a realistic chance, they are likely to continue investing in his campaign,” said Chergosky. “However, in addition to or instead of that, Republican megadonors may also be especially motivated to surge resources into crucial state Assembly races as the perhaps the most realistic bulwark against unified Democratic control.”

Chergosky questioned whether liberal megadonors would have been leery of sending money to Hong, given her democratic socialist brand and penchant for controversial statements.

“I do think Democratic megadonors are going to be opening up their wallets if they haven’t done so already, because Crowley is exactly the kind of candidate who the mainstream donor class within the Democratic Party can get behind,” said Chergosky.

Wisconsin’s general election ad war for governor has begun was originally published by Wisconsin Public Radio.