Lawyers of the Year: Max D. Stern and William Gildea

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Part of a series of profiles on our 2025 Lawyers of the Year.

Max D. Stern and William Gildea made an indelible mark on 2025 when they prevailed in a bitter, headline-grabbing feud between two high-ranking state officials.

The Todd & Weld Boston lawyers represent Shannon O’Brien, who in 2024 was unceremoniously booted from her position as chair of the Cannabis Control Commission by State Treasurer Deborah B. Goldberg on grounds of “gross misconduct.”

On Sept. 2, 2025, Superior Court Judge Robert B. Gordon overturned the firing after Stern and Gildea filed a certiorari action challenging the treasurer’s decision. The judge found Goldberg’s accusation of misconduct based on O’Brien allegedly making racially insensitive comments in the workplace and otherwise mistreating subordinates — accusations that O’Brien denies to this day — did not constitute “gross misconduct” under G.L.c. 10, §76(d)(4).

Challenge number 1 was that the person who was bringing this action, Deborah Goldberg, was a participant in the underlying facts, a witness to the underlying facts, the prosecutor in the action, the judge, the jury, and the executioner.

— Max D. Stern

In so ruling, the judge rejected the treasurer’s argument that while none of the alleged incidents alone may have constituted gross misconduct, the “bricks of misconduct” in totality built a “wall” of gross misconduct.

“[T]he Treasurer’s grounds for misconduct may look like bricks in shape, and edges and surface appearance,” Gordon wrote in ordering O’Brien’s reinstatement with backpay and benefits. “But viewed from any perspective other than the Treasurer’s, these bricks are as thin as playing cards.”

“The fact is, the treasurer was unable to get past these standards [for removal] by simply asserting that whatever she said is true and must be true,” Stern says.

Appeals Court Judge Gloria Y. Tan on Sept. 17 denied Goldberg’s motion to stay the Superior Court’s order of reinstatement, paving the way for O’Brien to return as chair of the CCC and serve out the remainder of her term, which expires in August 2027.

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Q. How did O’Brien’s ouster come about in the first instance?

STERN: The Cannabis Control Commission was a complete mess. It was supposed to be an unpolitical, independent agency. In fact, it was completely dysfunctional, composed of various fiefdoms inside the agency. The executive director, who was in charge of the day-to-day operations, was somebody who had been appointed by the treasurer, a former colleague of hers who was a close friend but completely incompetent.

The previous chair threw up his hands and gave up, and the treasurer [replaced him with] Shannon [O’Brien]. She was there just a few months and realized that the real problem was the executive director, who was the buddy of the treasurer. She went to the treasurer and told her he had to go. To which the treasurer said, “Oh, no, you won’t.” From then on, the treasurer and her people were looking for a way to get rid of Shannon. [Ultimately,] the treasurer suspended Shannon and started the [disciplinary] process to remove her from office.

Q. What were the main challenges in the case?

STERN: Challenge number 1 was that the person who was bringing [the disciplinary action to remove O’Brien], Deborah Goldberg, was a participant in the underlying facts, a witness to the underlying facts, the prosecutor in the action, the judge, the jury, and the executioner. She was completely biased but refused to recuse herself. That was who we were up against [in the underlying disciplinary proceeding].”

Plus, there’s the fact that [Goldberg] refused to give us a public hearing. It was an entirely private hearing. In fact, a record of the case wasn’t released for two years. The treasurer did everything she could to impound all the information in the case.

GILDEA: Mostly it was trying get an opportunity to be heard that was fair under the statute [governing the removal of CCC commissioners]. It felt like the treasurer was doing everything she could to not [afford O’Brien] an opportunity to be heard that would result in the actual facts to be presented to her.

Notably, there was an inability to call witnesses where two reports by investigators referenced a lot of people, some of whom were named, some of whom were anonymous. Had we been given the ability to call those witnesses and cross-examine them live, it would have told a different story than what appeared on paper in the reports.

Q. In your client’s Superior Court action, was it essentially a straightforward case in that it boiled down to showing the treasurer failed to follow the law in removing your client?

GILDEA: We thought it was straightforward in that the court would see the facts, see the [treasurer’s] allegations, see [the treasurer’s] findings, and rule [the evidence] did not rise to the level for removal under the statute. Gross misconduct is a high standard. And although that language had never been precisely defined in this context, our research of other jurisdictions and other cases made it clear that it was a very high standard.

For a second, separate ground for removal [asserted by the treasurer] — the inability to discharge duties — it was very clear to us early on that the language used in [G.L.c. 10, §76(d)] is almost identical as the language used in the 25th Amendment to the U.S. Constitution for the removal of the president from office, which we took to be physical disability. The treasurer took a much different position on that, but it was very clear to us that it was straightforward in that the court would understand that either the grounds for removal were met or they were not.

Q. Does the case have significance beyond the restoration of your client to her position as chair of the CCC?

GILDEA: Yes. There are three separate statutes for commissions in Massachusetts that currently have similar or identical removal language. It was important to define what gross misconduct means in this setting and what inability to discharge duties means in this setting. To the extent there are other removal proceedings, other attorneys will have guidance as to what the removal standards are.

STERN: And, of course, these statutory standards were put in place for the purpose of getting the politics out of the decisions made by a supposed “independent” agency. The fact is the treasurer was unable to get past these standards [for removal] by simply asserting that whatever she said is true and must be true.

Q. Were you concerned that state courts would defer to a decision by the executive branch of state government about a matter concerning the operation of a state agency?

STERN: That’s always a possibility. But we drew a judge who had his eyes open.