A National Black Org Funneled Dan Gilbert Dollars to Anti-Kucinich Super PAC. Then the Super PAC Went After Bibb.

The email under the "Contact" page is not in service and returns messages back to sender. - thesouthernstrategy.org
The email under the "Contact" page is not in service and returns messages back to sender.

A Washington D.C.-based organization devoted to building Black political power served as an intermediary for nearly $50,000 controlled by Cleveland Cavaliers owner Dan Gilbert during the 2021 mayoral primary, Scene has learned, and funneled it to Citizens for Change, the super PAC aligned with former city council president and mayoral candidate Kevin Kelley.

This financial arrangement was disguised by a campaign finance framework that delays donor identification in some cases and permits anonymity in others. And though it remained unpublicized, the arrangement inflected the response of the organization's founder, Quentin James, who felt duped—and, others have suggested, culpable—when Citizens for Change pivoted from bashing Dennis Kucinich to bashing Justin Bibb, and doing so with racist tropes. 

The D.C.-based organization is the Collective PAC. In August, it publicly endorsed Bibb, who went on to defeat Kelley in the November general election. A super PAC affiliated with it is called "The Southern Strategy PAC." Multiple sources with knowledge of the interaction said that this PAC was made available to accept Gilbert's money and that it then donated his funds to Citizens for Change after assurances that they would be used only to target Dennis Kucinich.

Why Gilbert preferred to cloak his involvement in the primary is a mystery, especially because he went on to donate $50,000, via his company Rocket Holdings, to another PAC, Citizens for Cleveland's Future, that was formed to back Kelley in the general.  The media relations team at Gilbert's Rocket family of companies has not yet responded to Scene's inquiries.

Update: Rock Holdings, as it turns out, did not openly donate to Citizens for Cleveland's Future. Ideastream reporter Nick Castele has confirmed that the $50,000 donation that was originally attributed to Rock Holdings was attributed to the Construction Employers Association in an amended FEC filing.

But regardless of his motives, The Southern Strategy PAC suited his needs. Like other 501(c)4s, contributions to it are not tax deductible, but donors retain the luxury of anonymity in most cases. Furthermore, for those who prefer to exert their influence behind the scenes, the Southern Strategy website is a veritable black box. It has no listed staff, for example. Its address is a P.O. Box in Washington, D.C. Its only social media presence is a dormant Facebook page, the entire activity on which transpired over one 24-hour period in August, 2020. The email address linked from its "Contact" button is inoperable. All messages are returned to sender.

Its mission, outlined on the website, is the engagement of "new and unlikely" voters, including Black people and suburban women "at the heart of the emerging Democratic coalition across the South and in states and districts where the greatest barrier to electoral success is sufficient and sustained financial investment." Beyond a $25,000 transfer to a related committee, The Southern Strategy PAC's only contribution in 2021 was to Citizens for Change. 

Scene managed to connect the dots only after after reviewing The Southern Strategy PAC's incorporating documents, which list a woman named Jennifer May as treasurer. May is the founder of a D.C. consultancy called Next Level Partners, which provides, among other things, compliance and accounting services for Super PACs. According to the Federal Election Commission, Jennifer May is also the Treasurer for the Collective PAC. Both PACs also share a P.O. Box.

To some in the Bibb camp, The Southern Strategy's activities smelled a lot like money laundering.

"Gilbert and Rock Holdings washed their money through [The Southern Strategy PAC]," one source with ties to the Bibb campaign told Scene.

But others said that, unfortunately, this was simply the nature of the United States' campaign finance laws.

"It's not [laundering]," said a source who spoke on condition of anonymity for legal reasons. "It's just the system. There are donors who are allowed to play in politics anonymously. The borderline illegal thing was Citizens for Change going to donors and saying we're going to do one thing, but then, by the way, we're actually doing another thing. Every donor could technically ask for their money back." 

According to recent disclosures published by the FEC, there were only 12 donors that backed Citizens for Change. These donors contributed more than $250,000 in a flood of big-ticket donations in August and September. The Southern Strategy PAC was among them.

Some of Cleveland's best-known oligarchs supported the effort: Browns owners James and Dee Haslam, ($44,000), who happen to be orchestrating a massive lakefront development plan to further enhance the value of their pro sports franchise; Greatest Generation tycoon Albert Ratner, ($42,500); Dick Pogue himself, (a paltry $2,500); Minute Men Staffing baron Jason Lucarelli, ($25,000); developer Wesley Finch, ($10,000); David Heller, President and CEO of the real estate development firm NRP Group, ($10,000); Randy Myerhoff, ($10,000), CEO of accounting firm Cohen and Co.; Miami's own Sheldon Guren, ($5,000); and technologist-titan Dan T. Moore, ($2,500), longtime Metroparks Commissioner and big-game hunter.  

Despite the towering wealth of these regional personages, it was the Cleveland Building and Construction Trades Council, presided over by the brash Dave Wondolowski of Broadview Heights, that donated the most total money to Citizens for Change: $50,000, in three separate donations.

But The Southern Strategy PAC was not far behind, and was in fact responsible for the largest single contribution: $48,250, on Sept. 2.

The day after that donation was processed, Citizens for Change modified its game plan in the primary. Though it had billed itself as a candidate-neutral PAC devoted exclusively to discrediting Dennis Kucinich and preventing the former Boy Mayor's return, everyone paying attention knew it was a Kelley operation. The Cuyahoga County Democratic Party's old guard—the infamous "Parma Boys," including County Executive Armond Budish's Chief of Staff Bill Mason, County Prosecutor Michael O'Malley and Wondolowski—were said to be pulling the strings.

When they saw that Justin Bibb was building momentum on Cleveland's west side, the only side that mattered to Kelley in the primary, Citizens for Change published a controversial mailer that appeared to darken Bibb's skin and purported to expose his ethical abuses and criminal history. The interior of the mailer documented a pattern of missed meetings during Bibb's tenure on the RTA board of trustees and showed a timeline of unpaid traffic tickets and landlord disputes.

Multiple sources have told Scene that the mailer was the brainchild of Wondolowski and Wondolowski alone. Others with knowledge of the Kelley machine told Scene that both Michael O'Malley and Roetzel & Andress attorney Galen Schuerlein—one of the architects of the failed attempt to thwart Chris Ronayne's candidacy for county executive—had a hand in conceptualizing the mailer's content and design. The mailer was printed using Qwestcom Graphics, the preferred vendor of the County Dems' rickety old guard. Citizens for Change paid Qwestcom $15,680 on Sept. 1, the only such expenditure in its paperwork.

Quentin James was furious when he realized he'd been misled or played for a fool, back in September. He uncorked a thread on social media on Sept. 7 that he said would "blow the lid" off Citizens for Change, "(aka Kevin Kelly for mayor Inc.)" (sic). 

In that thread, James outed O'Malley, Mason and Wondolowski as the trio behind the mailer and said its content was "designed to scare white voters from voting for Bibb because he's Black." This mailer was enough to disqualify Kelley from the race on its own, he wrote.

When Scene interviewed James on Sept. 7, he confirmed that he'd been approached to donate to Citizens for Change. Speaking in general terms, he said that "people" were outraged that the money they donated for a specific purpose (attacking Kucinich) was being used for a different one, (attacking Bibb).

At the time, James did not reveal the extent of his organization's involvement. Instead, he expressed displeasure with the nature of the Bibb mailer and Cleveland's political culture.

"The way they decided to attack Justin was completely below the belt," he said. "It was racist. It was unprofessional. And this behind-the-scenes lying is just amateur hour. These are three of the most powerful men in Cuyahoga County [Mason, O'Malley and Wondolowski] and this is how they behave? It's just sad."

James said he was relatively new to Cleveland but had already clocked how hesitant locals were to criticize those with power. That included Black leaders, he said. 

"I look around and they seem to be afraid to speak up against this fake machine politics," he said.

But when pressed for further details, James said he had already "put it all out there" on social media and didn't want to share specific names about who'd approached him and how.

When Scene contacted James in the wake of the FEC disclosure, he said he had no further comment, and was in any case not at liberty to discuss his PAC's donors.

But others with knowledge of the exchange said James was persuaded to use The Southern Strategy PAC as a vessel for Gilbert's money by Gilbert himself. The two of them were allegedly connected by Michael Bowen, the Calfee attorney and political operative who was enlisted to manage the latter half of Frank Jackson's re-election campaign in 2017.

Bowen's involvement in Citizens for Change had been previously known. His wife, Sarah Brandon, was listed on the PAC's incorporating documents. And Justin Bibb's campaign alluded to his influence in an email to donors on Sept. 3 after the controversial mailer was delivered.

"Citizens for Change, a Political Action Committee linked to a local attorney [Bowen], sent out a mailer today, which shows Cleveland politics at its worst," the email read. "It’s the same dirty tricks we’ve all seen before, desperately trying to keep power in the hands of the same old, same old self-serving powerbrokers. Today, we immediately refunded donations received from Michael Bowen and his wife, Sarah Brandon, who are behind this dark money PAC spreading misinformation."

In his capacity at Calfee, Bowen represents Dan Gilbert's Rock Holdings Inc. When reached by phone, Bowen declined to comment, but clarified that his involvement with Citizens for Change ended with the primary. Bowen was not the only non-donor who left the impression that the Bibb mailer was an aberration and a betrayal of trust. Veteran political consultant Jerry Austin, who was contracted by Citizens for Change, said that the Bibb piece had been designed and mailed without his knowledge. Others told Scene that they felt Bowen, who has long been personal friends with Bibb, had been thrown under the bus in the ordeal.

If Northeast Ohio's preeminent puppet masters were disturbed by the racist direction of the Bibb mailer, it didn't prevent them from ponying up in the general. Gilbert emerged from the shadows—or at least Rock Holdings did, when the FEC published the donor lists months after the election—to contribute $50,000 to the second PAC, Citizens for Cleveland's Future, created to support Kelley in his head-to-head matchup against Bibb. The Haslams and Al Ratner, via his family's RMS Investment Group, made additional contributions as well. So, too, did Wondolowski's group, Jason Lucarelli and Wesley Finch. 

All these Super PAC contributions were for naught, though, as Cleveland's moneyed interests and the goons at their disposal watched Bibb's margin of victory grow larger and larger on the evening of Nov. 2.

Having spectacularly bungled the Kelley campaign and made asses of themselves in their attempts to block a Chris Ronayne endorsement for County Executive, the party's old guard is now flailing to cling to power and relevance. The influence of their aging benefactors dwindles in lockstep. The Bibb victory, then, should serve as an airtight cap on an era of private cabals determining the city's succession planning behind closed doors. It was what it was, maybe, but should never be again.   

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About The Author

Sam Allard

Sam Allard is the Senior Writer at Scene, in which capacity he covers politics and power and writes about movies when time permits. He's a graduate of the Medill School of Journalism at Northwestern University and the NEOMFA at Cleveland State. Prior to joining Scene, he was encamped in Sarajevo, Bosnia, on an...
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