‘You want to be on’ team Cassi Fenili

The Democratic campaign manager pulled off a big win in the recent race for Supreme Court

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During the 2011 sleep-in protests in the state Capitol against Gov. Scott Walker’s union-busting efforts, staff from the Democratic Party of Wisconsin decided to make a show of solidarity and stay a night, too.

Among those staffers were Melissa Baldauff, then a party communications assistant, and Cassi Fenili, deputy membership director for the party. Both were one year into their jobs. Baldauff recalls lying on the cold marble of the Capitol’s floor as the two friends struggled to find a place to get some sleep.

Baldauff says Fenili was committed to the cause, despite the discomfort of the night.

“She is just a wonderfully kind and caring and compassionate person,” says Baldauff. “I know that’s why this work matters to her, because she truly cares about the people of the state and wants to help elect officials who will do the best thing for them.”

Baldauff, a former deputy chief of staff for Gov. Tony Evers, is now a principal for liberal-leaning communications firm GPS Impact. And Fenili, who in 2024 served as the party’s executive director, is fresh off a monumental win as campaign manager for Justice-elect Susan Crawford, whose 10-point victory over Judge Brad Schimel maintained liberal justices’ majority on the state Supreme Court.

“She was a no-brainer,” says Democratic Party of Wisconsin executive director Sarah Abel. “I don’t know who else you would want leading your campaign.”

Friends and colleagues say Fenili is Wisconsin’s premier Democratic campaign strategist — adroit at localizing issues, deeply connected to the needs of state communities, and focused when facing turmoil.

“This particular campaign had a lot of twists and turns as circumstances evolved,” says Crawford, who notes that Fenili “inspired confidence” from the moment the two met. “She was always on top of things, making the adjustments as we needed to adjust right up to the finish line.”

Says outgoing Democratic Party of Wisconsin chair Ben Wikler: “For any candidate who wants to win in Wisconsin, you want to be on the team with Cassi Fenili.”

A Kimberly, Wisconsin, native, Fenili knew she wanted to do something in the “legal” sphere after high school, but wasn’t sure what. She enrolled at UW-Madison in 2007 as a political science major and worked in the food court at Gordon Commons, but wanted to “be more involved.”

She applied for and landed an internship with then-U.S. Rep. Tammy Baldwin’s campaign for reelection.

“It wasn’t glamorous. I was opening mail and copying checks, but it was a good way to get in,” Fenili says. “That turned into an internship the next semester with the [state] Democratic Party, which turned into 15 years of a career.”

After years working in the party’s membership and finance divisions, Fenili became deputy campaign manager for Evers’ first race for governor in 2018; Evers unseated Walker with a 1% lead. She moved up to campaign manager for Evers’ 2022 reelection campaign.

“There’s no doubt her hard work and dedication has gotten me to where I am today as governor,” says Evers in a statement. “Our state is better because of Cassi’s leadership. I am so proud of her and I’m forever grateful for her hard work and friendship.”

Fenili also worked in 2020 state legislative races to prevent Republicans from gaining supermajorities. Her ability to raise money and localize messaging in those competitive districts, party officials say, alongside building a coordinated “Save the Veto” effort, were key to the victory. Democrats have since made further gains on the state legislative level using the same strategies.

“Her vision and strategy for how we were investing really paid off, and we’re well on our way to a trifecta,” says Abel, referring to the potential for Democrats to control the governorship, state Senate and state Assembly.

The 2024 state Supreme Court race quickly drew national interest with associated national consequences. Spending totaled $109 million, trouncing the $51 million judicial campaign spending record in the 2023 race between Janet Protasiewicz and Daniel Kelly.

“I don’t think anybody would have expected the level of attention that we had on this race in the end,” says Sam Roecker, a communications consultant on Crawford’s campaign, referring to Elon Musk’s $20 million in spending on the race.

Party officials praise Fenili’s careful, data-driven consideration of what advertising spots would work best in which markets, noting that her Wisconsin roots give her insight to what messages play beyond liberal bastions like Madison and Milwaukee. Part of the communications strategy, Fenili says, was also to establish a media plan “that allowed us to be on offense.”

“We had to fight to neutral on crime, and we knew that there were some real vulnerabilities [Schimel] had, whether it be [processing] rape kits [when he was state attorney general] or some of his sentencing decisions,” Fenili says. “[And] we wanted to win on issues like abortion that voters were still very passionate about.”

Both Schimel and Crawford ran ads that attacked each other for handing out light sentences and being a danger to public safety. The focus on these issues ignores the reality that state Supreme Court justices do not sentence criminals nor do they regularly consider issues of criminal law.

Fenili recognizes the contradiction, but says “it’s just the sad reality of what comes up in these races.”

“Do I wish this could be about each of their visions for what a Supreme Court should be, and that is enough to get it over the edge? Yes, I do, and I think mostly candidates want that too,” she says.

But, Fenili argues, crime is “at the top of voters’ minds” and “something they want to hear a candidate’s stance on.”

There is evidence for that view. A September 2024 Pew Research Poll found that violent crime was the third most important issue for those who identified as Trump voters. Sixty-one percent of all voters and 46% of Democrats said violent crime was “very important” to them in voting for a presidential candidate.

“Maybe it’s not something that they rule on, but it can give you an insight into the kind of decision-making process that each of these judges put into it,” Fenili says.

Fenili also concedes that the races for Supreme Court are only nonpartisan in name these days.

“Technically it is [nonpartisan], but it doesn’t feel that way anymore,” Fenili says, noting that Walker in 2015 successfully pushed to allow state parties unlimited transfers of funds to candidates. “Both sides are like, ‘This is what we have to do in order to fully utilize the laws that we have in order to win.’ It has become pretty partisanized.”

Sen. Kelda Roys, D-Madison, has recently floated introducing legislation that would limit all spending or donations for state Supreme Court races, including party transfers, to $20,000. Though Fenili hasn’t seen the legislation, she says she’s “very open” to spending restrictions in politics.

“I think voters are sick of seeing so many ads. I think that people are sick of how much money is being flooded into these campaigns,” Fenili says. “So, yeah, I am certainly in favor of, like, ‘Let’s limit this. Let’s make this a little bit more reasonable.’”

Fenili says she employs a few tricks to survive campaign pressure: having dinners to decompress with other campaign coworkers, “not abandoning” her personal trainer, and finding time to take her 8-year-old black lab/husky mix, Jack, on walks before it “gets pitch dark.”

“He’s the best,” she says. “I’m contemplating if I should get a second dog, but I’m like, ‘No. Vacation first.’”

Fenili puts to rest any rumors she will run for Democratic Party chair to replace Wikler, who announced in April he was stepping down after six years.

“I will be going on vacation while the rest of them are running,” she says, laughing.

Fenili anticipates returning to politics after her break. “I never intentionally decided to spend my entire career in Wisconsin, but now I’m here. This is my home state. I care about it. I wanted to beat Scott Walker, we did, and I want to support the wonderful people we’ve elected along the way.”