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cDermott told the Boston Globe that his real‑estate hobby has no bearing on the taxpayer‑funded expenses he’s incurred, arguing the money will “enhance my leadership skills and improve the office’s operations.” Yet watchdogs point out that the timing of the department’s business‑oriented spending and the launch of his personal venture raises doubts about the real intent behind the charges.
The “Off‑Market Millionaire Experience” is a 10‑member program that McDermott runs via monthly Zoom calls, drawing on his 18‑year tenure as Norfolk County’s register of probate. He insists it isn’t a business but a political tool to build his base. When state campaign‑finance regulators questioned whether he had used campaign funds to support the venture, he agreed to reimburse more than $36,000 from his personal and campaign accounts. The regulator’s agreement notes that McDermott presents himself online as a “seasoned real‑estate investor” and a mentor.
McDermott maintains that his campaign spending is aimed at strengthening his political future, a use permitted under Massachusetts law, and that the same money is meant to benefit the sheriff’s office he leads. His office’s procurement card recorded $265,000 in purchases last fiscal year—more than any other of the state’s 14 sheriff’s offices—though this is only a fraction of the nearly $40 million the department spent overall.
Key purchases include:
* $3,200 for a “Digital Course Academy” that promises to help subscribers create profitable online courses. McDermott says he plans to use the training to shift department instruction online and produce digital products for senior centers, though no content has yet been produced.
* $1,500 for an AI‑driven program that can generate flyers, eBooks, and other documents.
* $900 for a “leadership lab” course and $230 for a podcast‑creation course. He hopes to launch a podcast to showcase the office’s work, citing Florida sheriffs who attract large audiences.
* $1,700 for a subscription to “B‑School,” an online entrepreneurship program. He claims the lessons will help define the office’s mission, which focuses on prevention and re‑entry for incarcerated individuals, even though the course is not correction‑specific.
Mary Z. Connaughton of the Pioneer Institute calls the expenditures “questionable” and urges McDermott to reimburse the office unless he can demonstrate clear benefits to staff.
McDermott’s online presence promotes his real‑estate interests. In March he advertised the “Off‑Market Millionaire Experience” on LinkedIn and a Facebook group he created, offering a $670 annual membership for a four‑week course on profiting from probate properties. He warned that prices would rise to $97 a month if members did not sign up by late March. A group moderator posted a screenshot of a $670 invoice, and McDermott replied with celebratory emojis.
During a July post he shared photos of a neglected home, claiming he was “on the hunt for vacant, forgotten, or distressed properties” and asking followers to keep an eye out. In September he promoted a webinar on how he finds 20–40 probate leads weekly. In reality, McDermott says he has not actively flipped properties in roughly eight years; his company, McDermott Strategic Enterprises, dissolved in 2021 after buying and selling a single Braintree home. His financial disclosures show no outside income since 2021 and no other properties besides his Quincy home and one in the city. He states he has never received a stipend from speaking engagements and that the “Off‑Market Millionaire Experience” is a hobby, consisting of Zoom meetings with PowerPoint presentations and no employees.
When asked to clarify his social‑media description of the program, McDermott admitted he should have used better language.
