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Ocasio-Cortez Boyfriend Troubles Reveal the Corruption at the Heart of Her Campaign

Rep.-elect Alexandria Ocasio-Cortez, D-NY., arrives for orientation for new members of Congress.

Last week, an enterprising conservative political consultant unearthed evidence that Rep. Alexandria Ocasio-Cortez (D-N.Y.) may have hired her boyfriend, Riley Roberts, to work in Congress. This news actually unraveled a far bigger story of corruption, however. As it turns out, a political group helping Ocasio-Cortez's campaign had already paid Roberts during the campaign — and those payments from that shady organization may be the reason Ocasio-Cortez is in Congress today.

On Wednesday, Luke Thompson, a podcast host and former staffer for the National Republican Senatorial Committee (NRSC), shared some damning research into Ocasio-Cortez's campaign. He discovered more about the relationship between Riley Roberts and the campaign, but he also unearthed a humongous corruption story.

Luke Thompson had originally unearthed the central piece of evidence tying Ocasio-Cortez's congressional office to Riley Roberts — her boyfriend's official congressional staff email. In the wake of this news, some people noticed that the Ocasio-Cortez campaign paid Roberts $1,750, but Thompson insisted this was only "a means of keeping accounting in order." During the first half of 2018, the boyfriend volunteered with the campaign, and his efforts were classified as an in-kind contribution. This is normal.

Two far more conspicuous payments to Roberts came in 2017, however. Those involved Brand New Congress, an organization founded and run by Saikat Chakrabarti, who happens to be Ocasio-Cortez's chief of staff.

Chakrabarti founded Brand New Congress in 2017. "It’s a rather ingenious organization, but one that dwells in a legal gray-area as far as campaign finance law is concerned," Luke Thompson reported. "It facilitates campaigns on shoestring budgets by providing a single clearinghouse for campaign services, generally filed under the banner of 'strategic consulting'. But, as a result, it limits the meaningfulness of FEC disclosures by those campaigns," and it means that Brand New Congress "spends most of its budget on overhead and makes relatively few actual contributions to candidates."

Yet Chakrabarti's organization is really two organizations in one. "It’s a nonqualified political action committee — a PAC — that can raise and bundle campaign contributions for candidates. Donations and expenditures from PACs, like those to and by candidates, are publicly disclosed."

The organization also has an undisclosed component, however. "Brand New Congress is also a LLC [sic], owned by Chakrabarti, that provides campaign services to candidates to help lower the barriers to entry. LLCs do not have to disclose or itemize their spending," Luke Thompson explained.

The organization fully admits this on its "Frequently Asked Questions" page. "This LLC gets hired by candidates and by the PACs to actually run campaigns," the website explains. The group does this in order to "recruit and run non-career politicians" and "to run a big, single unified campaign" so as to "take advantage of various economies of scale."

The website admits that "the law does not allow tax exempt non-profits like 501c3s, c4s or PACs to exist primarily to provide services to campaigns." Brand New Congress LLC does not intend to make a profit, "but solely to support a new generation of leaders running for office." Chakrabarti claims not to make any money from the organization, although he is the owner.

"This is a clever way to try to make running for office easier and to place a lot of small bets on a lot of insurgent candidates and hope for a few lucky wins. And that pretty much seems to be what happened," Luke Thompson explained.

Brand New Congress PAC was founded in January 2017, and it's affiliated with Justice Democrats, a collaboration between Chakrabarti and The Young Turks's Cenk Uygur. Chakrabarti's LinkedIn profile lists him as co-founder of both organizations.

During the 2018 campaign cycle, Justice Democrats paid Brand New Congress LLC $605,849.12. These two organizations also shared an address: 714 South Gay Street in Knoxville, Tenn. Brand New Congress had its address there from May to August 2017, and Justice Democrats registered at that address in December 2017. Ocasio-Cortez used the same address in her first campaign filing, which registered her to run in New York's 15th Congressional District (she represents the 14th).

Less than a week later, she switched to the 14th district and added a campaign committee, registered to an address in the Bronx. Yet two months after that, the campaign committee's address changed — to 714 South Gay Street.

Luke Thompson argued that "Brand New Congress midwifed her campaign into existence, precisely as the FAQ described above would have it." Not only did Ocasio-Cortez win her campaign, but Chakrabarti became her campaign chair — and her chief of staff when she entered Congress.

Ocasio-Cortez paid Brand New Congress LLC a grand total of $18,880.14 for strategic consulting. Brand New Congress PAC paid her boyfriend Riley Roberts as a "marketing consultant."

Brand New Congress PAC's ten largest expenditures went to Brand New Congress LLC — for a total of $261,165.20 — but its eleventh and twelfth largest expenditures went to none other than Riley Roberts, Luke Thompson reported.

The timing of those two payments is also quite suspicious. Brand New Congress PAC paid Riley Roberts $3,000 in August 2017. Then Ocasio-Cortez's campaign paid Brand New Congress LLC $6,191.32 later that month. In September, Brand New Congress PAC paid Riley Roberts another $3,000.

Brand New Congress PAC paid Roberts for "marketing," but the candidate's boyfriend works in web development. As Luke Thompson pointed out, it makes no sense that Chakrabarti, "a founding engineer at Stripe and a wealthy veteran of Silicon Valley, [would] be hiring a no-name 'UX Experience' guy with little discernible marketing experience to serve as Brand New Congress PAC's sole marketing consultant."

According to a Vogue profile on Ocasio-Cortez, her boyfriend lives with her in New York. The congresswoman has referred to Riley Roberts as her "partner." Payments to Riley Roberts might as well be going to Alexandria Ocasio-Cortez, Luke Thompson reasoned.

Why would her campaign pay her boyfriend using Brand New Congress as a conduit? Perhaps Chakrabarti was trying to keep an exhausted candidate in the race.

"At the beginning of October, more than four months into her campaign, AOC’s fundraising had been anemic. Excluding an in-kind contribution from Chakrabarti, she’d raised only $3,032.75 but had already spent $27,591.27 — more than half of which she’d paid to Chakrabarti’s Brand New Congress LLC," Luke Thompson noted. "By the end of 2017 she’d spent $37,249.94 but raised only $8,361.03."

"That’s a lot of money to stick on a credit card. Since no loans are recorded on her campaign books, presumably either AOC or Roberts was fronting the necessary cash," he added. "It looks to me like Chakrabarti was effectively reimbursing AOC for a third of her expenses with Brand New Congress LLC, perhaps so that she would stay in the race despite her mounting debt."

Chakrabarti "funneling money to Roberts - who [Ocasio-Cortez] says is her spouse - is unethical and maybe illegal. And AOC didn't disclose this income, and didn't claim Roberts as a spouse, in her candidate financial disclosures," Thompson tweeted.

"When AOC won, she then hired Chakrabarti, her strategist/patron, as her Chief of Staff. Taking money from a rich guy, trying to hide it by passing it through a PAC, and then giving her benefactor a government job," Thompson wrote. Talk about sleazy.

Whether or not Ocasio-Cortez hired her boyfriend, giving him a government job, she certainly did hire Chakrabarti, whose organization effectively launched her campaign.

Worse, it appears she used Brand New Congress to funnel money back to herself when the campaign was in dire financial straits during 2017.

Adding insult to injury, Ocasio-Cortez has championed H.R. 1, congressional Democrats's effort to remake American voting as we know it. Should a woman with this checkered history be allowed to reshape America's system of government?

At the very least, this corruption muddies the waters of Ocasio-Cortez's success story. Democrats hail the young democratic socialist as a symbol of rags-to-riches democracy — a scrappy political novice and outsider defeating a well-established Democratic politician in the primary. These revelations suggest it wasn't so much the bartender from the Bronx who beat Rep. Joe Crowley (D-N.Y.), but rather the Silicon Valley veteran Sakrat Chakrabarti.

Alexandria Ocasio-Cortez represents one kind of Brand New Congress, but it isn't the idealistic vision of a new America. Rather, it's a shady political group that funneled money to her boyfriend.

Follow Tyler O'Neil, the author of this article, on Twitter at @Tyler2ONeil.