Infamous “Squad” member Rep. Ayanna Pressley (D-Mass.) tap danced around questions about her suddenly escalating wealth like Danny Kaye in White Christmas when reporters asked how she managed to get so filthy, stinking rich from a set of rental properties. Ever notice that many people—mostly Democrats—enter public service as middle-class folk and leave it in the top one percent? The Founding Fathers never intended legislators to turn representing their constituents into a wealthy, long-term career option.
In fact, early representatives and senators earned very little for their service because they believed their true payment came from helping build a free nation and preserve the rights of the people, themselves included. Most eagerly returned to their private businesses and jobs once their service ended. My, how times have changed.
Pressley responded to the questions by saying, “Sir, I submit a financial disclosure, just like everybody else. There’s nothing to see here.” That last line may have been the worst thing she could have said. Nearly every time someone says there’s “nothing to see here,” it usually means there is something that deserves scrutiny.
The Massachusetts congresswoman is hardly the only lawmaker who has attracted scrutiny for suddenly becoming wealthy after joining Congress. Her fellow “Squad” member Rep. Ilhan Omar (D-Minn.) has also drawn attention for her ever-expanding net worth.
But while Pressley continues to amass wealth, she has also taken on a significant amount of debt. Records indicate she currently sits roughly $9 million in the hole. Keep in mind, her congressional salary totals just $174,000. The most recent disclosure reports Pressley submitted show that two primary sources account for most of her new wealth.
One source comes from her husband’s Boston-based management consulting firm, Conan Harris & Associates, which generated between $100,000 and $1,000,000 in 2024. Notably, Harris founded the company in 2019—the same year Pressley began her congressional career. That’s probably just a coincidence, right?
Before launching his firm, Pressley’s husband worked for Boston Mayor Martin J. Walsh, earning $92,000 in 2018, according to reports. Just one year after starting the firm in 2019, he brought in $148,000. But this income does not represent the main driver behind the congresswoman’s accumulated wealth.
That distinction belongs to real estate. Pressley owns four rental properties in Mattapan, Boston, and Edgartown, all located in Massachusetts. Together, those properties generated between $95,000 and $250,000 last year. Another property in Fort Lauderdale, Florida—purchased in 2024—produced between $50,000 and $100,000.
The property holdings themselves have also proven lucrative, carrying a combined net worth between $2.5 million and $8 million. When Pressley first entered Congress, her initial disclosures listed three major debt obligations, all of which have since expanded their proverbial waistlines like Uncle Bob at Thanksgiving dinner. At the time, she owed between $610,000 and $1.2 million from two mortgages and an IRS-issued tax repayment plan.
“In her most recent reporting, Pressley reported between $3.25 million and $9 million in debt. All of her loans—made through Chase Bank, Bluestone Bank, Wells Fargo, United Wholesale Mortgage, and Crowd Lending Inc.—fund property acquisitions,” Fox News reported. She added to those liabilities throughout her time in Congress between 2019 and 2023.
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