The Congresswoman Loves the Swamp

Her Wealthy Chief of Staff used a PAC to Pay Her Boyfriend

Luke Thompson
Feb 20, 2019 · 8 min read

Last Friday, my mentions died for your sins. I posted a screen grab of Riley Roberts’s House Microsoft Outlook card, including his official email address, office phone number, and his designation as “Staff”. Roberts is the boyfriend of Alexandria Ocasio-Cortez. The Congresswoman was upset.

Throwing caution to the wind, she stormed into my mentions, asserting this was just a way to give Mr. Roberts access to her official calendar.

Her Chief of Staff, Saikat Chakrabarti, soon followed, reiterating the calendar claim and accusing me of doxxing Mr. Roberts by posting his publicly available LinkedIn profile (which he deleted) and his official government address and the office phone number.

Neither AOC nor Chakrabarti said why Roberts needs access to her official calendar.

Regardless, hordes of her howling minions followed. I was briefly suspended by Twitter for revealing personal information, only to be released with an apology when I pointed out that everything I posted is government property and public.

My Parole Papers

My brief stint as a digital political prisoner turned into something of a cause célèbre on the right, inviting wave upon wave of MAGA-enthusiasts to battle back on my behalf against the forces of digital socialism. My timeline is still a wasteland.

During my suspension I talked to a Congressional spouse, a few reporters, and some staffers from both parties. AOC hasn’t exactly been winning friends lately, which is how I got Roberts’s Outlook screen grab in the first place. A rumor on the Hill was circulating that Roberts had attended a Congressional Progressive Caucus meeting. A tipster looked to see if he’d been given staff credentials. It appeared he had. All agreed this was irregular if he was just a spouse.

Per the House Admin office, a family member can, in special circumstances, get a email address. But Roberts is not a family member, and although AOC referred to him as her partner in November of last year, she omitted him from her mandatory candidate financial disclosures for 2017 and 2018. Perhaps they’ve gotten married since. If so — if he is her spouse now — we should see his finances disclosed along with hers in her 2019 disclosure form due in May. But to be clear, AOC did not disclose Roberts’s finances as a spouse during her campaign.

Regardless, absent a wavier from House Ethics, family members have to be volunteers. AOC’s office apparently doesn’t believe in having unpaid workers, as according to Chakrabarti they have no volunteers in the office.

So Roberts is designated as staff but also isn’t on AOC’s staff, even though he showed up Friday morning in the House directory as processing into her personal office as a staffer. In other words his staff status, like his spouse status, is akin to Schrodinger’s cat.

This ought to have been enough to make it clear that AOC’s story didn’t add up. More importantly, I’d clearly hit a nerve. Chakrabarti spent much of the day in my mentions insisting that everything was on the up-and-up with Roberts. Instead of asking if Roberts had been supplied with the badge and pin appropriate to a Congressional spouse, evidence of which her office should have been able to produce easily, AOC’s worshipful stenographers in the press went into overdrive witlessly repeating her talking-points. Jeff Stein over at the Washington Post even woke up Saturday to keep it going in my mentions, as did Chakrabarti himself. And, of course, AOC had decided to get into it. That’s a lot of time and effort spent “refuting” a GOP consultant known to a tiny corner of the internet for posting cat pictures and bitching about the doctrine of coequal branches.

So I went to the FEC, did a little searching, and discovered that, lo and behold, there’s more to the story. Now, during the original kerfuffle, some folks noticed that AOC’s campaign had paid Roberts $1,750. That’s not quite what transpired. Roberts was “paid” only as a means of keeping accounting in order. In the first half of 2018, Roberts did some free work for the campaign. That work got put on the books as an in-kind contribution and then discharged as an expenditure for accounting purposes. That’s perfectly normal. It’s a way to keep people from circumventing federal contribution caps by providing discounted or free services.

But that’s not the only political work Roberts ostensibly did during the cycle. Nor would it be the first time Chakrabarti had hired Roberts. He’s done so at least once before, in 2017, although it’s unlikely Roberts was hired to do any actual work in that case.

At the beginning of 2017, Chakrabarti created Brand New Congress, an organization dedicated to shaking things up in Democratic primaries. It’s a rather ingenious organization, but one that dwells in a legal gray-area as far as campaign finance law is concerned. 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. Additionally, it means that Brand New Congress, unlike most PACs, spends most of its budget on overhead and makes relatively few actual contributions to candidates.

Additionally, Brand New Congress is not one thing, but rather two. 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. However, Brand New Congress is also a LLC, 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. Here’s Chakrabarti’s own write-up:

From Brand New Congress PAC’s FAQ page

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.

According to FEC records, the PAC was founded in mid-January of 2017. At the end of February, it affiliated with Justice Democrats, a collaboration between Chakrabarti and Cenk Uygur of The Young Turks. The two organizations are inextricably linked. Chakrabarti lists himself as a Co-Founder of both Brand New Congress and Justice Democrats on his LinkedIn page.

Over the course of the cycle, Justice Democrats would pay Brand New Congress LLC $605,849.12. They would also share an address. In May, Brand New Congress changed the address for its custodian of records to 714 South Gay Street in Knoxville, TN. In August, it switched addresses again, but in December of 2017, Justice Democrats registered at the address. AOC also used the Knoxville address in her first candidate filing, which incorrectly registered her to run in New York’s 15th Congressional District.

Five days later, she switched to the 14th district and added her campaign committee, registered to an address in the Bronx. Two months after that, the campaign committee’s address was changed to 714 South Gay Street as well.

A quick tour through AOC’s campaign expenditures reveals the extent to which Brand New Congress midwifed her campaign into existence, precisely as the FAQ described above would have it. But AOC’s campaign was different from the others backed by Brand New Congress PAC, and not simply because she won. Like other candidates, AOC paid Brand New Congress LLC for strategic consulting, in her case totaling $18,880.14. Unlike in the other cases, Brand New Congress PAC turned around and paid her boyfriend as a “marketing consultant”.

Indeed, while Brand New Congress PAC’s ten largest expenditures were paid to Brand New Congress LLC for “strategic consulting,” a sum that totaled $261,165.20 over the course of the campaign, its eleventh and twelfth largest expenditures were paid to Riley Roberts.

Brand New Congress PAC paid Roberts $3,000 on August 9th:

Payments from Brand New Congress PAC to Riley Roberts

Eighteen days later, AOC’s campaign paid Brand New Congress LLC $6,191.32:

Payments from AOC’s Campaign to Brand New Congress LLC

A month later Brand New Congress PAC then turned around and paid Riley Roberts another $3,000.

Why would Chakrabarti, a founding engineer at Stripe and a wealthy veteran of Silicon Valley, be hiring a no-name “UX Experience” guy with little discernible marketing experience to serve as Brand New Congress PAC’s sole marketing consultant?

The answer seems to be that Chakrabarti was funneling money paid to him by AOC’s campaign back to Roberts and by extension to AOC.

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. 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.

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.

The shadiness of the whole business may also explain why Roberts lists his residence as Arizona for the expenditure, rather than New York. Roberts is from Arizona, but was living in New York with AOC. His other contributions to her campaign, both cash and in-kind, list New York as his residence.

Regardless of whether or not Roberts was officially AOC’s spouse at that time, it seems probable Chakrabarti was reimbursing her for her campaign expenses off-books. Brand New Congress PAC simply served as a pass-through to do so.

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.

That’s definitely unethical and potentially illegal. Chakrabarti may have made an illegal campaign contribution in excess of federal limits. Regardless, it raises questions about Chakrabarti’s hiring as AOC’s Chief of Staff after her election. Maybe add that to your next lightning round, Congresswoman.

Finally, all of the above is based on public information. It took me a couple of hours to pull it all together and write it up. I suppose this could be called muckraking, but it’s really just minimal reporting that nobody in the press decided to do. I can’t emphasize enough how easy it was to find all of this information. It’s literally just sitting there. But no reporter bothered to read it. Democracy dies in darkness? Nah. Reporters are just lazy.

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