David Crowley is not spending Monday night in Milwaukee, Waukesha, or Green Bay. He is in Santa Monica, California, chasing $20,000 VIP checks from the same coastal set that already watched Kamala Harris spend a fortune and lose.
The flyer promotes special guests: Sean Penn and “Vice President Kamala D. Harris.” VIP reception starts at 6 p.m. Suggested contributions run from $500 for guests up to $20,000 for VIP.
Wall Street Journal reporter Ken Thomas posted the invite Saturday. By Sunday, Rep. Tom Tiffany was already on it. “First, David Crowley was in D.C. rubbing elbows with wealthy elites. Now, he’s off to California,” Tiffany wrote. “Wisconsin doesn’t need Crowley’s California-style policies.”
Harris is an interesting choice. The last-minute substitute candidate is trying to assert herself as the 2028 frontrunner while quietly hoping people forget about her failed candidacy. In 2024, she and her allies raised well over $1 billion, spent most of it, and still lost the White House and Wisconsin. Reports put her campaign’s burn rate near $1.5 billion in roughly 15 weeks. She left almost nothing in the bank and plenty of second-guessing about celebrity events, private jets, and ads that didn’t close. Now the same operation is supposed to teach Crowley how to win Wisconsin from a living room in Santa Monica.
The pairing is less odd than it looks. Both campaigns were rescue jobs. Harris never won a single primary vote in 2024. Party bosses yanked Joe Biden and dropped her onto the ticket with 107 days to invent a message. She never did. Asked on The View what she would have done differently from Biden, she said, “There is not a thing that comes to mind.” Trump’s campaign turned that into an ad. Voters wanted a break from inflation, a failed border czar, and an unpopular White House. She was an empty vessel that offered “joy,” then loyalty to the same record, with a heaping side of word salad. She is still floating a 2028 candidacy. Former aides and donors have called that “obviously a bad idea.” Crowley looked at her record and decided she’s still someone he needs in his corner.
Crowley’s candidacy is the state-level version of the same Kamala Harris stunt. On July 8, he quit the governor’s race and said it was clear he would “not be the Democratic nominee.” He endorsed Sara Rodriguez. Ten days later, Rodriguez’s campaign’s embarrassing bookkeeping implosion, Tony Evers fished Crowley out of the discard pile, and the party tried to pass him off as the electable alternative to Francesca Hong. A Marquette poll after he reentered had him at 7 percent, with a third of Democrats still undecided. He beat Hong by about 3,700 votes, less than half a percentage point, after Evers barnstormed the state with him. Hong had a message, even if it was a radical one. Crowley had a rescue line. Now he is in Santa Monica selling $20,000 access to the last Democrat who also had to be installed at the last minute, could not explain what she stood for, and still lost.
Sean Penn is the other headliner. Tiffany’s campaign called him a “socialist and dictator sympathizer.” Penn spent years defending Hugo Chavez, called him a “model democrat,” and argued that journalists who labeled Chavez a dictator should face punishment. He later said Chavez had been his friend and that he had seen “improvements” in Venezuela. Venezuela’s subsequent collapse into shortages, exile, and authoritarian control is the part Hollywood usually skips. Penn also has a long public record of assault cases and jail time. Crowley is forced to turn to these people when he needs cash.
Crowley wants voters to believe he is the pragmatic moderate who saved Democrats from Francesca Hong. His record as Milwaukee County executive tells a different story. Property and sales taxes have gone up on his watch. His administration has floated a 26 percent levy increase for 2027. He built racial-equity budgeting into county spending, expanded the equity office, signed net-zero climate plans, and asked the attorney general to sue fossil fuel companies. Tiffany’s campaign has also highlighted Crowley’s line on illegal immigration: “I’m not an ally, I’m an accomplice.” That is not a Wisconsin campaign strategy, but it’s perfect for California donors.
The contrast is evident: Tiffany is holding events in Wisconsin. Crowley is selling $20,000 access in Santa Monica with a failed presidential candidate and an actor who thought Chavez was the future. Wisconsin voters have seen this movie. High taxes. Sanctuary politics. Hollywood lectures. Then the bill arrives in property taxes and grocery prices.
Crowley’s California junket looks more like a candidate who cannot hit his fundraising quarter goals in his own state, so he is outsourcing the effort to people who have already proven they can raise a fortune and still lose. Wisconsin is not Santa Monica. The $20,000 crowd does not have to live with the policies. Wisconsinites do
