Milwaukee County Executive David Crowley told a reentry group he shares its vision, the same outfit whose CEO once pushed to build a whole community for sex offenders.
David Crowley, the Democratic Milwaukee County executive now running for Wisconsin governor, stood as the featured speaker at the It Takes a Village Foundation’s annual gala in November 2024 and offered the group a full-throated endorsement.
“I want to tell you, Dr. Whitehead, that Milwaukee County, we share in your vision,” Crowley said, according to a Washington Free Beacon report.
He did not stop there. Crowley cast the county as a partner on workforce development, affordable housing, and easier pathways for mental health and substance use treatment, and he said officials were “standing beside” the foundation to foster a more equitable and compassionate Milwaukee County.
Two years earlier, foundation founder and CEO Shawna Whitehead had described a far more specific idea on a podcast: buy land, build houses, and create an entire community for sex offenders.
It Takes a Village Foundation, founded by Whitehead in 2020, says it helps people leaving prison through online classes, job training, and housing. The group boasts that it has aided nearly 4,000 former inmates.
On the 2022 “At The Roundtable” podcast, Whitehead framed sex offenders leaving jail as people with nowhere to go.
"It really bothers me that we have sex offenders that's coming out of the jail now... and you mean to tell me they have nowhere to go."
She then laid out the plan in plain terms.
"So you got these people out here like leprosy. So my thing is that I'm trying to challenge, and God showed me I want to get some partners together where we buy some land, and we start building houses and create a whole community for our sex offenders."
Whitehead knew the idea would land hard. “See, it's outside the box. I know everybody got quiet on that one,” she said.
Crowley’s gala remarks did not quote that language. He spoke about sharing “your vision,” moving “the vision of Dr. Shawna,” and refusing to care about “perceptions” or “the narrative.” He tied county support to housing, jobs, and treatment pathways while standing beside the same leader who had floated a dedicated sex-offender community.
The foundation’s website has featured a video testimonial from Kevin Pettis, presented as a reentry success story. Archives show the testimony went up around the start of this year.
Court records show Pettis was convicted in 2002 of first-degree sexual assault of a child. Wisconsin’s sex offender registry lists him as “non-compliant,” a status the Wisconsin Department of Corrections describes as failing to meet Sex Offender Registry Program requirements.
Pettis was convicted in 2017 for a sex registry violation. In 2024 he faced the same charge again, and a warrant for his arrest was issued the same day. It is unclear when he completed the foundation’s program. The foundation did not answer questions about whether it knew he was non-compliant when it published the testimonial.
Whitehead has also coauthored a book titled A Successful Way to Entrepreneurship and Obtaining Wealth. The Free Beacon reported that the book recommends “opening an offshore account” to secure “asset protection from lawsuits” and “decrease vulnerability.”
Crowley’s Republican opponent in the governor’s race, U.S. Rep. Tom Tiffany, has made crime a campaign focus and highlighted an endorsement from the Wisconsin Fraternal Order of Police.
At a recent event, Tiffany charged that Crowley has long backed weaker criminal penalties.
"For years, he has supported policies that would weaken criminal penalties."
Tiffany went further on specific votes and bills.
"David Crowley supported legislation to lower penalties for bail jumping. He voted against allowing judges to consider a defendant's criminal record, the seriousness of the crime and the threat to public safety when setting bail."
Those claims sit alongside Crowley’s public pledge of county partnership with a reentry group whose leader once called for a purpose-built community “for our sex offenders,” and whose website later showcased a child-sex-assault convict listed as non-compliant on the state registry.
Crowley’s gala message left little daylight. He told the room Milwaukee County shares Whitehead’s vision, promised continued support, and said he does not care what the perceptions or the narrative are.
Voters now get to decide whether that partnership, and that shrug at public concern, match what they want from the next governor.
When a county executive running for higher office lines up behind a group that floated housing sex offenders together, taxpayers have every right to demand straight answers before anyone else gets the keys.
