Milwaukee

With Election Day a week away, Illinois Democrats are campaigning beyond state lines to aid party allies nationally. Rep. Raja Krishnamoorthi backed Texas Railroad Commissioner candidate Jon Rosenthal; Sen. Tammy Duckworth campaigned for Sherrod Brown in Ohio; Rahm Emanuel canvassed in New Hampshire; and Rep. Danny Davis and successor nominee La Shawn Ford campaigned for Wisconsin gubernatorial candidate David Crowley. Gov. JB Pritzker is focused on his own reelection, holding a large cash advantage and backing fellow Democrats financially.

Big money is also flowing into Illinois races, including Chicago school board contests, with GOP megadonors Dick and Elizabeth Uihlein and wealthy Democratic-aligned groups both spending heavily to shape outcomes from Springfield to Chicago.

Rep. Tom Tiffany, the Republican candidate for Wisconsin governor, said during a debate that private election funding dubbed "Zuckerbucks" — grants from a Mark Zuckerberg-backed nonprofit that helped Wisconsin communities run elections during the pandemic — was a key reason he objected to certifying the state's 2020 results and backed Trump's bid to disqualify absentee ballots from Milwaukee and Dane counties. Democratic opponent David Crowley called the explanation inadequate, noting Tiffany alleged no actual fraud, and questioned whether Tiffany could be trusted to certify 2028 results. Tiffany pledged he would certify the 2028 election regardless of outcome. Wisconsin voters later banned private election grant funding via constitutional amendment.

U.S. Rep. Tom Tiffany, the Republican candidate for Wisconsin governor, said in a debate that private election grants funded by Mark Zuckerberg — dubbed "Zuckerbucks" by critics — drove his support for Trump's efforts to overturn Wisconsin's 2020 results. Tiffany also cited Milwaukee and Dane County clerks allowing "indefinitely confined" voters to skip photo ID requirements. Over 200 Wisconsin communities received roughly $10 million from the Zuckerberg-funded Center for Tech and Civic Life during the pandemic; voters later banned such private election funding via a 2024 constitutional amendment. Democratic opponent David Crowley argued Tiffany's explanation was inadequate and questioned his trustworthiness to certify 2028 results, though Tiffany pledged he would certify regardless of outcome.

U.S. Rep. Tom Tiffany, the Republican candidate for Wisconsin governor, said during a debate that his 2020 objection to certifying Wisconsin's presidential election results stemmed from private election-administration grants funded by Facebook founder Mark Zuckerberg, dubbed "Zuckerbucks" by critics. More than 200 Wisconsin communities received about $10 million from the Zuckerberg-backed Center for Tech and Civic Life during the pandemic. Tiffany also cited Milwaukee and Dane county clerks allowing "indefinitely confined" voters to skip photo ID for absentee ballots. He backed Trump's failed bid to disqualify 220,000 absentee ballots and voted against counting Pennsylvania and Arizona electoral votes. Democratic opponent David Crowley questioned whether Tiffany can be trusted to certify 2028 results; Tiffany said he would.

In a Wisconsin governor's race debate, Republican U.S. Rep. Tom Tiffany said his 2020 objections to certifying Wisconsin's election results stemmed from concerns over election funding from Meta founder Mark Zuckerberg, often called "Zuckerbucks." Tiffany pointed to grants from the Zuckerberg-funded Center for Tech and Civic Life, which sent about $10 million to more than 200 Wisconsin communities during the pandemic, and to Milwaukee and Dane county guidance letting voters claim "indefinitely confined" status to get absentee ballots without photo ID. Democratic opponent David Crowley argued Tiffany identified no actual fraud and questioned whether he would certify the 2028 results; Tiffany said he would, "regardless of who the winner is."

U.S. Rep. Mark Pocan's Madison office received a suspicious piece of mail on Oct. 19, prompting a hazmat response from the Madison Fire Department. Staff recognized it as matching mailings sent to officials around the country containing an unidentified powdery substance; the envelope was not opened and its contents were sent for testing. Similar mail was earlier received by U.S. Rep. Gwen Moore's Milwaukee office and the Wisconsin Elections Commission. Other targets reportedly include election offices in Oklahoma, Louisiana and Ohio, plus Sen. Chuck Schumer, Sen. Kirsten Gillibrand, Sen. Chris Murphy and Sen. Lisa Blunt Rochester. The FBI and U.S. Postal Inspection Service are investigating and working to identify those responsible ahead of the election.

With roughly a month until Wisconsin's election, Democratic candidate David Crowley is drawing criticism, including from some supporters, for spending limited time campaigning directly within the state. Crowley recently traveled to California for a fundraiser headlined by Kamala Harris and actor Sean Penn, and made two trips to Washington, D.C. this month seeking financial support from national Democrats. Republican opponent Tom Tiffany has significantly outraised and outspent Crowley, according to fundraising reports.

Crowley re-entered the race over the summer after initially dropping out, with Democrats citing concerns that a different candidate could lose to Tiffany in November. Critics note that Crowley has held comparatively few in-state campaign events, including rallies or town halls in Madison, while Tiffany has been touring Wisconsin broadly, holding events in cities including Milwaukee. The dynamic has drawn comparisons to Harris's 2024 presidential campaign, when questions were raised about limited outreach in some traditionally Democratic areas before her loss. The race is viewed as a competitive contest that could factor into broader midterm turnout and party strategy debates.

A Milwaukee County judge set $1 million cash bail for Casimer Kobylinski, 71, a Sheboygan chiropractor accused for the second time in a year of possessing child pornography. Authorities say hundreds of child pornography images were found on a USB drive seized from his Casey Chiropractic Clinic, including AI-generated images of underage girls. Prosecutors allege Kobylinski also took inappropriate photos of two girls, ages 2 and 10, while free on bail from his original February 2025 case.

Judge David Borowski forfeited Kobylinski's earlier $45,000 bail, ordered him to live in Sheboygan instead of Milwaukee, and barred him from having a cellphone. He separately faces 11 felony possession charges in Sheboygan County, where he posted $650,000 bail in September, plus multiple bail-jumping counts in both counties. He pleaded not guilty to 22 charges on September 23. His chiropractor license remains active, and his next Milwaukee County court appearance is scheduled for September 25.