When Massachusetts congresswoman Ayanna Pressley spoke at a film festival in celebrity hideaway Martha's Vineyard last month, she clearly felt at home.
The Vineyard Gazette reported that she was in her 'happy place' and likes to visit her 'chosen family and community' there as often as possible during the summer. Indeed, Pressley and her husband, Conan Harris, like the affluent enclave so much that he appears to have recently bought a $1million rental property there.
The pricey acquisition is a far cry from the vibe of the front line of rowdy protests and feisty rallies where members of the 'Squad' - a group of progressive Democratic congresswomen including Pressley, Alexandria Ocasio-Cortez and Ilhan Omar - are often seen. Their finances are currently in the spotlight after a series of increasingly wild claims by their opponents that they are secretly worth large sums, which they have strongly refuted.
The charming two story, three-bedroom home in Martha's Vineyard is located less than a 10-minute drive from where the Pressley, a firebrand left-wing congresswoman, was speaking at the African American Film Festival in August.
The home - which features a patio and spacious back garden - is just one of four rentals Harris has purchased. It is located on the picturesque island off Cape Cod, which is a favorite of the Obamas, the Clintons and Taylor Swift..
Harris, who once served 10 years in jail on drug trafficking charges, is now a successful consultant and campaigner for reintegrating former inmates 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'sOffice 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 opportunity every family.Her record speaks itself.'
Meanwhile,fellow Squad member Omar,the congresswoman from Minnesota has recently faced accusations being secretly wealthy.Critics claimed she a 'hypocrite.'
Omar's apparent penchant wearing Prada Jimmy Choo sunglasses costing hundreds dollars has not gone unnoticed.
With congressional salary $174,000 she may well have bought sunglasses herself.But also reasonable assume could been purchased husband,a venture capitalist owns part wine company California.
According to Omar's financial disclosures her husband Tim Mynett 44 appears have experienced remarkable surge business success very recently.
Earlier Omar's career used Mynett's consulting firm E Street Group during 2020 election campaign paid $2.9 million services.
At time responded criticism payments saying:'You don't stop using service people doing good work because somebody thinks means something else.'
But she later stopped using husband’s firm.
In 2023 Mynett’s share wine business eStCru Santa Rosa California listed Omar modest asset worth between $15,000 and $50,000.
Rose Lake Capital his venture capital management firm listed worth less than $1,000.
But fast forward year and her husband’s winery share worth between $1million and $5million Rose Lake Capital between $5million and $25million.
Omar herself did not make any money Rose Lake Capital.She declared ‘partnership income’ between $5,000 and $15,000 wine company according congressional filing.
It is fair to say she does not agree with suggestion that her husband’s success makes her millionaire.
Speaking on TikTok recent days she said it was ‘lying’ say she had ‘millions dollars’ brandished own financial disclosure form.
‘So if you look this document see says assets unearned income. If look asset for $1million to $5million income $5,000 to $15,000.
‘And if you look asset for $5million to $25million it says "None." Right there. Learn read before post misleading s*.’
She added that doesn’t own home stocks.
Indeed, despite suggestions vast wealth, records show she still owes between $15,000 and $50,000 student loans dating back 2005.
And her husband, despite paper being worth potentially tens millions dollars, has credit card liability between $15,000 and $50,000.
As for most famous member Squad,Ocasio-Cortez,financial records seem much clearer.
The 35-year-old New York congresswoman filed one simplest financial disclosure forms.
She has no connection rental property empire,wine venture capital firm web mortgages.
In New York,she rents 1,000-sqare-foot apartment 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.