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Milwaukee Set To Accept $800K From A Cryptic Elections Group With Democrat Dark Money Ties

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Milwaukee is expected to accept a nearly $800,000 election grant from a nonprofit with ties to a prominent left-wing dark money group.


The city of Milwaukee, Wisconsin, is expected to accept a nearly $800,000 election grant from a newly-formed nonprofit with ties to a prominent left-wing dark money group.

On Monday, Urban Milwaukee revealed that the Democrat stronghold — in a county Joe Biden won by nearly 40 points in the 2020 election — has been offered a $796,500 election grant from Cities Forward, a virtually unknown nonprofit organization that markets itself as a “nonpartisan effort focused on helping cities around the country make participation in the democratic process a priority.”

Milwaukee is expected to use the funds from the group to pay for new tabulators to process ballots; a text messaging service that “would allow the city to reach registered voters to correct misinformation or answer questions”; voting machines that “can digitally generate a ballot for any voter in the city and then print a paper copy”; more than 200 Android smartphones “for the chief inspectors at each polling place” that will reportedly permit “site directors to submit photos or videos of any equipment issues and more easily request supplies”; and “signs, an electric pallet jacket and a table trolley.”

Cities Forward is also expected to gift a separate grant of unknown value to the Milwaukee Public Library to explore, as Urban Milwaukee described, “ways to encourage civic engagement.” Speaking with the outlet, Claire Woodall, the executive director of the Milwaukee Election Commission, claimed the purpose of this grant is to connect “people to their city services” and help “them navigate those programs.” Woodall further indicated the funds would go towards efforts to register new voters.

“At the library, when people are registering for a new library card, they will also be asking ‘do you want us to help … register you to vote today?'” Woodall said, adding that the Milwaukee Health Department would employ similar tactics at its various facilities throughout the city that regularly engage with local residents. These monies are expected to support the creation of a communications campaign, street “outreach team,” and new website, according to Urban Milwaukee.

The Milwaukee Common Council’s Judiciary & Legislation Committee is expected to consider the former grant on Thursday, while the council’s Finance & Personnel Committee is slated to consider the latter on Friday.

Alarming Connections

Aside from its mission statement, not much is known about Cities Forward. The group’s website lacks any information about its origins or membership. Moreover, the nonprofit told Urban Milwaukee it would file its 990 form “no later than November,” so information about its financial backers and expenditures is not yet known.

What little information is available about Cities Forward, however, reveals a startling connection to a prominent left-wing dark money group.

According to Urban Milwaukee, Cities Forward is spearheaded by Trevor Ostbye, who previously worked at the Democracy Fund. As noted by InfluenceWatch, the Democracy Fund “contributes to center-left and left-wing media organizations, groups seeking to infringe on campaign speech rights, left-of-center voter registration organizations, and nominally non-aligned public policy organizations.” It has also financially supported left-wing voter registration groups, such as the Voter Registration Project, and was created by eBay founder Pierre Omidyar, who regularly donates to Democrat-aligned causes and organizations.

While Urban Milwaukee indicated Ostbye currently serves as Cities Foward’s executive director, his LinkedIn account shows that he occupied the role from December 2021-2023. Cities Forward did not respond to The Federalist’s request for comment on whether Ostbye still serves as executive director.

Prior to working for Cities Forward, Ostbye regularly aligned himself with other leftist groups. He was listed as a contributor on a 2014 report published by the left-wing Lawyers Committee for Civil Rights Under Law and its brainchild, the Election Protection Coalition. The report regurgitated Democrat lies that voter ID requirements “disproportionately disenfranchise African Americans, Latinos, the elderly, youth, people with disabilities and lower-income citizens.” It also parroted claims that laws mandating individuals provide proof of citizenship when registering to vote are “restrictive.”

Ostbye was also a listed participant for a multi-day event titled, “Exploring Civic Learning as a Pathway to Equity and Opportunity.” Hosted by the National Conference on Citizenship and Philanthropy for Active Civic Engagement, the March 2018 event sought to “open a dialogue about how to reimagine, re-incorporate, and maximize the potential of civics during this divisive time; enable communities to build an inclusive foundation of engaged citizens; and embrace and position civic learning as part of a solutions set to addressing challenges, particularly inequity and lack of opportunity.”

More recently, Ostbye contributed to a report published last year called “The Democracy Protection Playbook,” which advised left-wing activists “primarily” in “red states” on how to register and turn out new voters, including those in jail who are “eligible” to vote. Report author Shanna Singh Hughey — who previously worked as senior legal counsel on the Biden-Harris transition team — baselessly claimed this is because “[v]oters in these states typically face much higher hurdles at the ballot box, and their legislatures further restricted voting access after the 2020 election or kept voters’ already-low access the same.”

Hughey recommended these activists use the president’s overreaching “Bidenbucks” executive order to expand voter registration activities in their states; partner with the Justice Department to challenge Republican-backed election integrity laws they believe run “afoul of federal protections”; and encourage their local officials to join left-wing organizations such as the U.S. Alliance for Election Excellence.

To put the cherry on top, FEC filings show that Ostbye donated $50 to ActBlue, a Democrat fundraising platform, in 2017. The donation was earmarked for Democrat Doug Jones’ 2017 Alabama Senate campaign against Republican Roy Moore.

This Isn’t Milwaukee’s First Dance with the Dark Money Devil

This isn’t the first time Milwaukee has accepted money from nefarious actors for the purposes of administering elections.

During the 2020 contest, the Center for Tech and Civic Life and the Center for Election Innovation and Research collectively received hundreds of millions of dollars from Meta CEO Mark Zuckerberg. These “Zuckbucks” were poured into local election offices in battleground states around the country to change how elections were administered, such as by expanding unsupervised election protocols like mail-in voting and the use of ballot drop boxes. To make matters worse, the grants were heavily skewed towards Democrat-majority counties, essentially making it a massive Democrat get-out-the-vote operation.

According to the Capital Research Center, Wisconsin received $10.1 million in “Zuckbucks” from CTCL, which “distributed a total of 31 grants above the $5,000 minimum to Wisconsin cities and townships.” Of those 31 grants, 28 went to cities, eight of which were won by Trump and 20 by Biden. Milwaukee received the fourth largest amount of funds per capita, behind Racine, Green Bay, and Kenosha, respectively.

In her bestselling book, Rigged: How the Media, Big Tech, and the Democrats Seized Our Elections, Federalist Editor-in-Chief Mollie Hemingway highlighted the role Woodall played in coordinating with CTCL officials ahead of the 2020 election. As noted by Hemingway, once early voting began, Woodall provided Michael Spitzer-Rubenstein — an out-of-state Democrat activist who was heavily involved in Green Bay’s 2020 election operations — with “a daily update on the numbers of absentee ballots returned and still outstanding in each ward.” This came weeks after Spitzer-Rubenstein reached out to Woodall to offer “an experienced elections staffer that could potentially embed with your staff in Milwaukee in a matter of days.”

“Amazingly, [Spitzer-Rubenstein] even asked for direct access to the Milwaukee Election Commission’s voter database,” Hemingway wrote. “Even for Woodall[], who had been providing daily reports to the Democratic activist working for the nonprofit, that was too much.”

Woodall denied Spitzer Rubenstein’s request, writing: “I am definitely not comfortable having a non-staff member involved in the function of our voter database, much less recording it.”

Milwaukee’s acceptance of the Cities Forward grants comes weeks before Wisconsin electors will vote on a constitutional amendment proposal that seeks to prohibit election officials from accepting money from private actors to conduct elections. The election is set to take place on April 2.

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