A U.S. national security agency that metes out sanctions against foreign terrorists and rogue regimes placed a hold in 2022 on investment funds raised by "Squad" member Ilhan Omar's (D., Minn.) husband and his business partner, the partner claimed in emails later cited in legal filings. The claim of a mysterious hold came while Omar sat on the House Foreign Affairs Committee, and two years before she was reportedly investigated by the Biden Justice Department for her "interactions with a foreign citizen."
The alleged freeze by the Office of Foreign Assets Control, or OFAC, came to light during a legal dispute involving a failed marijuana venture run by Tim Mynett—Omar's third and current husband—and his longtime business partner, Will Hailer. Mynett and Hailer, both former Democratic operatives, have been behind a string of business flops and have been accused in multiple lawsuits of lying to investors and not paying their bills.
In August 2022, when angry investors sued Hailer demanding the return of millions of dollars he'd raised from them for Badlands Ventures—a trio of business entities cofounded by Hailer and Mynett that sought to invest in South Dakota marijuana businesses—he said he could not return the money because it had been frozen by OFAC.
The investors argued that Hailer and Badlands "moved at least some—and perhaps all—of Plaintiffs' $1.683 million out of Badlands Ventures' bank account for purposes other than Badlands Ventures' business" and that the money had been "misappropriated and/or stolen." They added, "Hailer promised to wire hundreds of thousands of dollars … but claimed that the Office of Foreign Assets Control ('OFAC'), which enforces economic sanctions in the financial system, had placed a hold on the funds."
The plaintiffs were confused. "This explanation makes no sense, as all of Badlands Ventures' funds came from Plaintiffs who reside domestically," they said in a lawsuit alleging Hailer and Mynett formed Badlands "with the present intention of stealing and/or misappropriating" their money.
Middle East Forum policy analysis director Michael Rubin said an OFAC hold is not a matter to be taken lightly. OFAC, part of the Treasury Department's Office of Terrorism and Financial Intelligence, administers trade sanctions against foreign terrorists and regimes that pose a threat to U.S. national security.
"OFAC is a technocratic agency; they don't defer to political spin," Rubin told the Washington Free Beacon. "So for a hold to be put on the funds suggests the scheme involved diversion of money to some very, very bad people."
It's unclear whether Hailer was being truthful about the alleged OFAC hold against his marijuana business. The Free Beacon was unable to independently confirm if the agency has ever placed a hold on any known business entities associated with Mynett and Hailer. Hailer claimed he and the businesses he founded with Mynett were financially insolvent in discovery documents released as part of the Badlands case in February 2024 yet somehow managed to repay the scorned investors later that year.
The Treasury Department did not return requests for comment.
Taken at face value, Hailer's claim that OFAC placed a hold on Badlands' assets in August 2022 suggests that Omar and her family have been under scrutiny from federal law enforcement for their finances and foreign ties since before Republicans retook the House of Representatives in 2023 and Donald Trump returned to power in 2025.
Omar was serving on the House Foreign Affairs Committee, which conducts oversight of OFAC, at the time Hailer told his investors the agency had seized control of the funds of his and Mynett's marijuana firm.
The New York Times reported in January that the Biden Justice Department in 2024 opened an investigation into Omar "to scrutinize her finances, campaign spending and interactions with a foreign citizen." The Times said the probe "appears to have stalled for lack of evidence."
But scrutiny on Omar and her family has only intensified.
She is under investigation by the GOP-controlled House Oversight Committee over her and Mynett's finances after the Free Beacon reported that her net worth surged to between $6 million and $30 million in 2024, fueled by her husband's stake in two businesses. Omar later drastically reduced her net worth, citing an accounting error. She is also facing intense political scrutiny amid a major federal criminal probe into entitlement fraud in the Minneapolis Somali community. During his denunciations of the fraud scandal, Trump has repeatedly suggested that Omar is under investigation, though he hasn't specified why.
"I would imagine they're looking at her. I have nothing to do with it," he told a crowd at the Villages in central Florida earlier this month. "Isn't she despicable?"
On Wednesday, in the White House Cabinet Room, Trump, while condemning alleged corruption among Minnesota's Somali diaspora, said, "Ilhan Omar, crooked as Hell. They're all crooks. And we got 'em. … We're putting the clamps on."
A Failed Marijuana Venture
Omar's wealth is derived almost entirely from the value of her husband's various companies, several of which have been sued by investors, reported just dollars in the bank in the course of legal proceedings, and then miraculously turned up hundreds of thousands if not millions of dollars to repay angry investors.
Take Badlands, which was a conglomeration of three entities—Badlands Ventures, Badlands Fund, and eST Ventures—all of which were formed by Mynett and Hailer (Mynett told the Minnesota Reformer he left eST Ventures just before the angel investors say Hailer duped them into investing their $3.5 million into the operation).
In August 2022, when the investors first requested their funds back, Badlands returned $1.9 million in the form of equity in Badlands. Hailer said he couldn't return the remaining $1.7 million in cash because OFAC had placed a hold on the funds.
Still, Badlands managed to scrounge together $500,000 to return to the investors in October 2023. The next month, the investors filed another lawsuit, this time in Nebraska, seeking the return of the final $1.2 million. By this time, however, Hailer claimed he was financially destitute. Now-sealed discovery documents from the Nebraska case reviewed by the Minnesota Reformer show that eST Ventures had just 5 cents in its bank account in February 2024. Hailer himself wasn't doing much better. He claimed to have just $3.05 in his personal checking account.
Yet just five months later, in July 2024, Badlands repaid the final $1.2 million owed to the angel investors. The source of those funds remains an enduring mystery to the investors, one of whom told the New York Post he was "shocked" Hailer was able to come up with the money so shortly after claiming financial insolvency.
A similar fact pattern transpired with a $780,000 lawsuit filed in October 2023 against eStCru—a now-defunct California winery owned by Mynett and Hailer—from a disgruntled Washington, D.C., businessman who said the pair duped him into investing in the winery on false representations about the business. That company had just $650 in its bank account in February 2024, according to discovery documents in the Nebraska lawsuit, and its winemaker, Erica Stancliff, told the Minnesota Reformer she abruptly stopped getting paid in early 2023.
Hailer and Mynett still found a way to pay that debt as well. The D.C. businessman, Naeem Mohd, dropped his $780,000 lawsuit against the winery in November 2024. "We did settle and the amount was paid," his attorney told the Free Beacon last year.
The winery—which produced wines with names like "Blockchain" and "Clothesline"—filed to terminate its California business license in April. In legal filings, Mynett and Hailer blamed COVID.
How Mynett and Hailer managed to come up with the cash to settle the winery lawsuit is also a mystery, considering the company appears to have engaged in no business activities in 2024.
Mynett and Hailer's international venture capital firm was doing even worse in 2024. Rose Lake Capital had just $42.44 in its bank account in February 2024. Its related firm, Rose Lake Inc., had just $10 in its account, according to the Nebraska discovery record.
Hailer testified during the bankruptcy proceedings of the Indian educational technology company Byju in November 2024 that Rose Lake Capital provides consulting services to "global operators in the business space" but had no assets under direct management and had never made an investment with its own capital, which likely explains why the firm never registered with the Securities and Exchange Commission.
Still, with no money in the bank at the start of 2024 and no assets or investments at the end of 2024, Rose Lake Capital managed to pull together $213,000 that year to distribute directly to Mynett, according to records reviewed in April by the Wall Street Journal that contradict a Rose Lake spokesman, who told the Post in January that Mynett netted less than $20,000 from all his companies in 2024.
It's unclear where Rose Lake obtained the funds it distributed to Mynett in 2024. Hailer testified in the Byju bankruptcy case, however, that Rose Lake received two wires totaling $11.25 million in June 2024 in connection with a failed deal to acquire Byju's Term Loan B, the $1.2 billion leveraged loan at the center of its bankruptcy proceedings. In a sworn declaration, Hailer said Rose Lake received the wires in part to show the firm had the funds necessary to acquire the Term Loan B, as well as "to pay for our services."
But the source of the $11.25 million was unclear to Hailer and Rose Lake. Hailer said he was initially told the funds originated from a Cayman Island firm run by Indian billionaire Ranjan Pai, that they were routed to Rose Lake "from Dubai to Mauritius to the UK to the USA," and that the funds were Rose Lake's "to have as a fee."
Days later, however, Hailer said Byju Raveendran, the Indian billionaire owner of Byju, demanded the return of the $11.25 million. Hailer said Byju informed him the funds did not actually come from Ranjan and that if he didn't return them, "it was going to cause criminal or civil issues for Byju in Dubai because of UAE law."
Hailer said Rose Lake later discovered the $11.25 million came from a U.K. firm called OCI Limited, which had previously been used as a financial vehicle for Byju.
A Delaware bankruptcy court ordered Raveendran to pay $1.07 billion stemming from issues surrounding Byju's Term Loan B. It's unclear from Hailer's testimony whether Rose Lake ever returned the $11.25 million it received in June 2024, or whether the funds were used to resolve the Badlands marijuana lawsuit or the eStCru winery lawsuit. Hailer did not return requests for comment.
What isn't a mystery is that Mynett and Hailer were trying to become international venture capitalists as Omar sat on the House Foreign Affairs Committee. Hailer briefly described the ambitious plans he and Mynett developed for Rose Lake Capital during his testimony in the Byju bankruptcy case in November 2024.
"Back in 2023 we had put together a full sort of advisory team, a strategy of countries that we would want to enter into, and a U.S. [Business to Government] distribution strategy. So it certainly was something I was very passionate about," Hailer testified during the Byju bankruptcy proceedings in November 2024.
It didn't seem to work out for Rose Lake Capital, however. House Republicans expelled Omar from the Foreign Affairs committee in early 2023 after she repeated antisemitic tropes, such as claiming that U.S. support for Israel was "all about the Benjamins." And Rose Lake Capital's once-vaunted advisory team was a façade, with several of its members since alleging Hailer and Mynett added their names without their consent.
One individual named as a Rose Lake Capital adviser told the Free Beacon he met with Mynett once for five minutes and with Hailer a handful of times to discuss a potential investment in an energy project in South Africa.
"That deal never went anywhere and I never had any agreement or ever received a dime from Rose Lake Capital," the former adviser said. "I was much surprised later to find out I'd been listed as an advisor and asked them to remove me."
Another former Rose Lake "adviser," former senator Max Baucus (D., Mont.), offered a similar account of his experience with the firm, telling the Post that he discussed a proposed storage unit deal with Hailer in 2022 and 2023, but nothing came of it.
"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 said.
Rose Lake has since taken down its website. Hailer told the Reformer that the firm had been restructured into a public benefit corporation that does so-called socially responsible investing.
Mynett's LinkedIn headline is now "Committed to doing good in the world."
