Last month, Congresswoman Ayanna Pressley felt right at home when she addressed attendees at a film festival in the celebrity retreat of Martha’s Vineyard.

The Vineyard Gazette noted that Pressley was in what she described as her ‘happy place,’ frequently visiting her ‘chosen family and community’ there during the summer. In fact, the appeal of this upscale enclave is so strong for Pressley and her husband, Conan Harris, that he seems to have recently acquired a $1 million rental property in the area.

This valuable purchase is quite a departure from the scene of lively protests and spirited rallies where the ‘Squad’ — a group of progressive Democratic congresswomen including Pressley, Alexandria Ocasio-Cortez, and Ilhan Omar — often make appearances. Their financial activities have come under scrutiny following a series of bold allegations by opponents suggesting they possess substantial hidden wealth, claims that have been vehemently denied.

The quaint two-story, three-bedroom residence on Martha’s Vineyard is less than ten minutes by car from where Pressley, a passionate left-wing congresswoman, delivered her remarks at the African American Film Festival in August.

This home, which boasts a patio and large backyard, is one of four rental properties acquired by Harris. It is situated on the scenic island off Cape Cod, a locale favored by the Obamas, the Clintons, and Taylor Swift.

Harris, who once spent a decade in prison for drug trafficking offenses, has since transformed his life into a prosperous career as a consultant and advocate for the reintegration of former prisoners into society.

Pressley documented the newest piece of her husband’s burgeoning property empire on her latest congressional financial disclosure form. She also noted three others in Boston, a city she represents in Congress. 

A fifth property in Fort Lauderdale, Florida, was sold in September last year for $492,000.

Although they are not owned by Pressley herself, the number of properties involved may sit uneasily with followers of the ‘Squad,’ a group which has proudly brandished its credentials as warriors for the working class.

Congressional financial disclosures allow politicians to declare their income in ranges, rather than requiring precise figures.

Pressley’s latest filed documents show the Martha’s Vineyard property is valued between $1 million and $5 million. Other property records show Harris purchased it for $1.1 million in September 2024.

Two of the Boston residential properties were each valued between $500,000 and $1 million on her forms. The third was valued between $250,000 and $500,000.

Pressley declared Harris’ annual rental income from the Martha’s Vineyard property as being between $15,000 and $50,000.

The total annual income from all four rental properties, which all goes to Harris, was reported as being between $95,000 and $250,000.

On September 5, 2024, Harris sold the Florida property. His income from capital gains and rent for part of the year was listed by Pressley as being between $50,000 and $100,000.

It is all a long way from Pressley’s own first property purchase.

Back in 2008, she bought an 871-square-foot, one-bedroom, one-bathroom apartment in Boston for $237,500. The mortgage was $190,000.

In 2019, the year she entered Congress, she sold it for $397,000.

That year, Harris had a lien served against him by the US government for $17,430 in unpaid federal taxes.

Harris explained there had been a ‘miscommunication’ in a previous tax year, and as soon as he found about the lien, he paid it off. He said it did not involve his wife in anyway.

After coming out of prison well over a decade ago, Harris has performed a remarkable life turnaround. He eventually rose to become Deputy Director for the Mayor’s Office of Public Safety in Boston, where he earned $92,500.

In 2019, the year his wife entered Congress, he left to start a consulting business, Conan Harris & Associates. 

His current income is stated on his wife’s financial disclosures as between $100,000 and $1 million.

Despite the numerous properties, the couple may not be as wealthy as appearances suggest.

In her disclosure forms, Pressley declared one relatively modest mortgage herself, which is between $100,000 and $250,000, and lists another four for her spouse.

That includes one incurred in 2019 for between $500,000 and $1 million on the couple’s primary Massachusetts residence, ‘and a rental unit within the same building.’

There is another mortgage for between $1 million and $5 million, taken in September 2023 on a ‘primarily personal residence.’

And there are two more on rental properties for between $500,000 and $1 million, and between $250,000 and $500.000.

All five mortgages were taken out with different creditors.

Separate records for the Martha’s Vineyard property show Harris took out a 30-year mortgage, for slightly more than the $1.1 million sale price. 

‘The congresswoman and her husband met later in life and keep their finances separate,’ a spokesperson for Pressley told the New York Post recently.

‘Like many families, they have navigated significant economic hardship including medical debt, incarceration, predatory student debt – and the Congresswoman is a steadfast champion for economic justice and opportunity for every family. Her record speaks for itself.’

Meanwhile, fellow Squad member Omar, the congresswoman from Minnesota, has recently faced accusations of being secretly wealthy. Critics have claimed she is a ‘hypocrite.’

Omar’s apparent penchant for wearing Prada and Jimmy Choo sunglasses costing hundreds of dollars has not gone unnoticed.

With a congressional salary of $174,000, she may well have bought the sunglasses herself. But it is also reasonable to assume they could have been purchased by her husband, a venture capitalist who owns part of a wine company in California.

According to Omar’s financial disclosures, her husband, Tim Mynett, 44, appears to have experienced a remarkable surge in business success very recently.

Earlier in Omar’s career, she used Mynett’s consulting firm, the E Street Group, during the 2020 election campaign. She paid $2.9 million for its services. 

At the time, she responded to criticism of the payments, saying: ‘You don’t stop using the service of people who are doing good work because somebody thinks it means something else.’

But she later stopped using her husband’s firm.

In 2023, Mynett’s share in a wine business, eStCru in Santa Rosa, California, was listed by Omar as a very modest asset worth between $15,000 and $50,000.

Rose Lake Capital, his venture capital management firm, was listed as being worth less than $1,000.

But fast forward a year and her husband’s winery share was worth between $1million and $5million, and Rose Lake Capital between $5million and $25million.

Omar herself did not make any money from Rose Lake Capital. She declared ‘partnership income’ of between $5,000 and $15,000 from the wine company, according to her congressional filing.

It is fair to say she does not agree with the suggestion that her husband’s success makes her a millionaire.

Speaking on TikTok in recent days, she said it was ‘lying’ to say she had ‘millions of dollars’ and brandished her own financial disclosure form.

‘So, if you look at this document, you can see it says assets and unearned income. If you look at the asset for $1million to $5million, the income is $5,000 to $15,000.

‘And if you look at the asset for $5million to $25million, it says “None.” Right there. Learn to read before you post misleading s***.’

She added that she doesn’t own a home or any stocks.

Indeed, despite the suggestions of vast wealth, records show she still owes between $15,000 and $50,000 in student loans dating back to 2005.

And her husband, despite on paper being worth potentially tens of millions of dollars, has credit card liability of between $15,000 and $50,000.

As for the most famous member of the Squad, Ocasio-Cortez, financial records seem much clearer.

The 35-year-old New York congresswoman filed one of the simplest financial disclosure forms.

She has no connection to a rental property empire, winery, venture capital firm or web of mortgages.

In New York, she rents a 1,000-sqare-foot apartment with her fiancé, web developer Riley Roberts.

The apartment was last sold in 2022 for around $600,000.

The rent is believed to be between $3,000 and $4,000 a month. She also rents another apartment in Washington for an unknown amount.

‘I am not even worth $1million. Or a half million. I am one of the lowest net worth members of Congress, trade no individual stock and take no outside income,’ she recently said.

But if she decides she wants to visit Martha’s Vineyard, Pressley may be able to help her out with a place to stay.