A longtime Democratic operative who worked for top party figures before jumping into private ventures with the now-husband of Rep. Ilhan Omar, D-Minn., Tim Mynett, is back in the spotlight as swindling allegations resurface and Congress investigates Omar’s skyrocketing net worth via her husband’s companies, according to her financial disclosures.

William Hailer and Mynett, who met working for now-Minnesota Attorney General Keith Ellison when he was in Congress, were both political operatives before they turned to venture capitalism and the wine industry. Hailer was a senior advisor to former Democratic National Committee Chairman Tom Perez and also has an extensive history working for Ellison, who was the DNC co-chair. Between consulting fees and reimbursements, Hailer raked in over $250,000 advising the DNC and Ellison, according to FEC filings.

The pair also co-founded the political consulting firm E Street Group, which raked in almost $3 million alone from Omar’s House campaigns, and then went on to co-found Rose Lake Capital LLC, a venture capital firm, and eStCru, a wine company, among a web of other ventures they have since embarked on. 

Through these business ventures, which include wine and cannabis, Hailer left a trail of fraud and swindling allegations tied to eSt Ventures, which was co-founded by Hailer and Mynett, and the subsequently formed Badlands Fund, which was created to control another investment fund that the pair also created called Badlands Ventures.

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“On information and belief, Defendants formed Badlands Ventures in order to defraud Plaintiffs by soliciting them for purported investments in Dakota and 605 with the present intention of stealing and/or misappropriating most of the money,” the cannabis lawsuit, which listed Hailer and Badlands Ventures as the defendant, states.

The lawsuit claims that the pair solicited donations from local South Dakota cannabis growers who had been raising money among their friends and family. Hailer allegedly promised them that he already had big investors lined up, and would bring in multi-millions more if the local growers forked over around $3.5 million. 

However, the additional investment never appeared to materialize despite months of promises that the funds were not far away, according to court complaints. While the money has since been returned, according to public reporting, the defendants claimed that after signing a proposed settlement they were still struggling to get the full amount that they gave to Hailer back. Hailer returned $1.86 million in August 2022 and another $500,000 in October 2023, while the final settlement in 2024 got the remaining $1.2 million back to the investors that was still missing. 

The cannabis investors’ attorney eventually said the dispute was settled “amicably.” Meanwhile, local media questioned how Hailer was able to pay the money back considering discovery documents in the case reportedly showed he had less than $750 combined across various business and personal bank accounts.   

Following the cannabis incident, Hailer and Mynett faced further allegations of fraud related to their California wine business, eStCru, which saw its valuation jump from between just $15,000 to $50,000 in 2023 to between $1 million and $5 million in 2024. 

The winery first appeared on Omar’s disclosure reports after she and Mynett tied the knot in 2020 and the massive valuation jump comes just five years after Hailer complained that eStCru could barely keep the lights on during the COVID-19 pandemic. “ESTCRU LLC like many wineries is living invoice to invoice, sale to sale, to stay afloat given the economic conditions of the industry,” Hailer told the Minnesota Reformer in response to more fraud allegations against him and his wine business with Mynett.

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The situation involved similar promises left unkept aimed at drawing in investors. The business deal involved a D.C.-area restaurant owner who was recommended to invest in Hailer and Mynett’s wine venture by his attorney, Faisal Gill, who also happened to be a former Democratic operative as well, per the Rhode Island Current. “I trusted Tim,” Gill told the outlet. “If it was not for Tim, the deal would have never happened.”

The restaurant owner, Naeem Mohd, wired $300,000 to Hailer and Mynett, but alleged he never received the 200% returns in 18 months that the pair promised him, arguing the pair knew that the promises were false. Hailer and Mynett also allegedly promised 10% monthly interest payments for as long as the restaurant owner did not see returns, but once again the investor argued that the pair knew this would never come to fruition.

Mohd also alleged in court filings that Hailer and Mynette pressured him into signing an agreement preventing him from filing further suit against them.

In response to the accusations of fraud, a spokesperson told Fox News Digital for the pair’s venture capital firm responded that “Any disputes with these parties have been settled with cases dismissed with prejudice (can not be brought again).” 

Hailer and Mynett’s Rose Lake Capital, the other firm that saw a massive valuation jump on Omar’s financial filings, was listed as being worth between $1 and $1,000 in 2023 and then skyrocketing to between $5 million and $25 million the following year.

Amid the scrutiny into the firm’s massive jump in valuation shown in Congresswoman Omar’s most recent financial filings, the firm co-founded by Hailer and Mynett came under fire for scrubbing their firm’s website of various high-profile individuals that it said were its advisors. Among those listed were former members of Congress and other well-connected persons, including former Sen. Max Baucus, D-Mont.

The New York Post reported that Baucus said he had several phone calls with Hailer back in 2022-2023 about a proposed deal to make storage units. “Then nothing came of it” beyond occasional emails from Hailer, Baucus told The Post. “That went on for about four or five months or so, then just radio silence.” 

“He stopped writing his emails about the investment – about how well he’s doing, all that stuff. You can read between the lines – it sounded a little bit fishy,” Baucus told The Post.

Baucus did not respond to Fox News Digital’s requests for comment. 

In a statement to Fox News Digital, a spokesperson for Rose Lake Capital denied that there was anything irregular about Senator Baucus’s engagement with Rose Lake.

A spokesperson for Rose Lake defended removing the names from its website, noting that it did so in response to “hate-filled messages.”

“All names were removed from the website when hate-filled messages were being sent to various members listed by individuals who have read stories in various publications,” the spokesperson told Fox News Digital.

Hailer and Rose Lake Capital were also embroiled in a Chapter 11 bankruptcy case that included allegations Hailer was encouraged to leave the country so he wouldn’t have to testify and would disrupt the sale. When asked during the bankruptcy hearing why he didn’t get on the flight to Dubai in order to skip the hearing, Hailer said, “Sometimes it’s better to do the right than the easy thing.”

Currently, both congressional and federal investigators are looking into the massive valuation jump by Hailer and Mynett’s venture capital fund and wine business. The scrutiny follows backlash from the 2019 – 2020 election cycle, during which Omar was caught funneling millions in campaign cash to a firm Mynett co-founded with Hailer called the E Street Group. 

The expenses covered a range of services, including cable advertising, “digital consulting,” video production and editing. Omar claimed that her relationship with her husband began long after her campaign started working with his firm. The payments, while not illegal, generated backlash for Omar and her husband.

In 2021, Republicans in Congress introduced the Oversight for Members And Relatives Act or “OMAR Act,” aimed at closing the loophole in federal anti-nepotism law that permitted Omar to funnel her campaign cash to Mynett and his firm.

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“For too long, lawmakers of both political parties have engaged in the ethically dubious practice of pocketing campaign funds by ‘hiring’ their spouses and laundering the money as campaign related expenses,” Rep. Tom Tiffany, R-Wisc., said at the time. 

The fresh scrutiny into Omar and her husband comes amid rampant fraud uncovered in Minnesota under the purview of Democratic Party leaders that estimates say could amount to as much as $9 billion in missing funds, and questions on whether Omar or anyone else benefited from it. The fraud has involved various social services and welfare schemes, including Medicare and childcare funding, and many of those convicted have been part of Minnesota’s ballooning Somali population.

Fox News Digital reached out to Hailer, Mynett, and Omar’ office.

Editor’s Note: This article has updated the quote attributed to former Senator Baucus to reflect updates made to the New York Post article from which this quote was drawn and to include an updated statement from a spokesperson for Rose Lake Capital. 

Sam Dorman, Peter Hasson and Fox News Digital’s Leo Briceno contributed to this report.