Milwaukee County Executive David Crowley spent Monday evening at a Santa Monica fundraiser alongside former Vice President Kamala Harris and actor-filmmaker Sean Penn, seeking a cash infusion for his uphill campaign for Wisconsin governor. The trip comes as Crowley, the Democratic nominee, trails Republican opponent Tom Tiffany badly in fundraising with just days left before state campaign finance reports are due.
A West Coast Stop for a Wisconsin Race
According to the Milwaukee Journal Sentinel, the fundraiser was held in Santa Monica, California, and asked donors for contributions ranging from $500 for a guest ticket up to $20,000 for VIP access. Crowley is Milwaukee County executive and the Democratic candidate for governor, having unexpectedly won his party's primary after what the paper described as a chaotic contest. Harris, the former vice president who lost the 2024 election to President Donald Trump, and Penn, an actor and filmmaker, both appeared at the event with him.
Tiffany's campaign wasted no time criticizing the trip, framing it as evidence Crowley would import California policies to Wisconsin if elected. Tiffany, the Republican vying to succeed the current administration, said that as governor he will not let what he called the California playbook happen in Wisconsin. He argued Crowley wants to bring higher taxes, more crime and higher prices to the state, adding that Wisconsin cannot afford them, per the same report.
A Lopsided Money Race Heading Into Filing Day
The fundraiser lands at a pointed moment financially. As of August, Tiffany had raised approximately $15.6 million compared with roughly $1.8 million for Crowley. Tiffany also reported more than $10 million from the Republican Party of Wisconsin and the Wisconsin Federation of College Republicans as of August, with the state party drawing funding from billionaire donors Richard Uihlein, Elizabeth Uihlein and Diane Hendricks.
Crowley's campaign did not immediately respond to a request for an interview about the fundraiser, the Journal Sentinel reported.
Campaign finance reports are filed with the Wisconsin Ethics Commission.
Star Power Versus a Cash Gap
For Crowley, the appeal of aligning with Harris and Penn is straightforward: both carry national profiles that can draw bigger checks than a Wisconsin-only circuit likely could on its own. But the optics cut both ways, and Tiffany's campaign has moved quickly to cast the Santa Monica gathering as proof that Crowley's politics are shaped more by coastal allies than by Badger State voters, according to the Journal Sentinel's reporting.
With reports due imminently and Tiffany holding what the paper describes as a commanding fundraising lead, the Santa Monica trip is unlikely to close the financial gap on its own. Whether it helps Crowley narrow the deficit in the weeks ahead, or simply hands his opponent another talking point, may not be clear until the next round of filings becomes public.
