Some operators might not want to hear it, but the simple truth is that no gaming sector could function without a strong regulator. Legal or illegal, gambling has taken place throughout history and will continue ever-more. It is human nature, after all. As countries around the world – along with states across the US – have discovered, the answer is to regulate the activity, endeavouring to ensure the practice is as safe and responsible as possible. It will never be a panacea. But it is the best viable option if you have a regulator that is responsive, proactive and co-operative with the industry – being firm when needed but equally open to an exchange of ideas.
That’s where a good gaming regulator comes into play. And, in Massachusetts, that’s where Cathy Judd-Stein comes into play.
Judd-Stein, Chair of the Massachusetts Gaming Commission, now boasts a storied background in gaming. Her career in its entirety, however, is a blend of gaming, law and politics – a journey that began with Judd-Stein’s attendance of Dartmouth College and none other than Harvard Law School. To this day, Judd-Stein’s Dartmouth class continues to be a “really important” part of her life. So much so that there is a weekend party in New Hampshire the Saturday after Gambling Insider’s conversation with her. The “entire class is a little bit crazy” – but she adds that they’ve “been there for each other” during both times of personal hardship and professional development.
As for Harvard, Judd-Stein humbly looks back hoping she “hasn’t disappointed” those who admitted her to the Law School. She recalls: “When I was accepted, I suspect many have a little bit of imposter syndrome, so I was stunned and instantly recognised that being part of Harvard’s extensive network was a huge privilege. It was an incredible experience to spend three years there with the benefit of brilliant peers and really great professors; professors who were very empathetic. I didn’t expect it, but I just have really warm feelings from my law school classes – not in accordance with the movies!”
Indeed, Judd-Stein is able to draw on one particular stereotype-defying example that resonated with her. One might immediately assume a Harvard professor would be more demanding than empathetic – and there were naturally demanding elements of attending Harvard Law School. For instance, students had to be prepared to answer a professor in a lecture hall on cue if called upon; there were no do-overs. But, during a particularly sensitive and important class, Judd-Stein’s professor gave her and some fellow students a “heads up” in advance. The class addressed the subject of rape, the first time ever this had been taught at a law school – back in the 1980s – meaning it would receive coverage in the news (not your ordinary university seminar). As such, Judd-Stein’s professor ensured her and her fellow students were not caught off guard. That professor was “very highly regarded” and, in Judd-Stein’s opinion, showed a willingness to break barriers and push limits through her students.
To see our team members present complex matters and have to deal with our sometimes pretty thorny questions on the fly; it’s not lost on me how difficult that is – and I’m super proud of them
Life before gaming: The Governor’s Office
As the Chair of the Massachusetts Gaming Commission, Judd-Stein’s role within the gambling industry today is clear for all to see. Starting out, though, her gaming experience was initially limited to her French-Canadian grandmother inviting her to play the occasional game of bingo! Judd-Stein does not even recall playing the lottery, so at this point, a career in gaming remained very much a distant prospect. After law school, her first move was to take up a “fantastic clerkship” that led her to a large law firm in the real estate sector – carrying out “very complex development deals.” “I love that transactional work,” Judd-Stein states. “I like the tangible outcomes.”
Judd-Stein also undertook additional pro bono work (work without payment), which ultimately led to another private law firm. It was here that a chance cocktail party meeting determined the most significant step of Judd-Stein’s career to date. “The Chief Legal Counsel to then Governor Paul Celucci here in Massachusetts was at a cocktail party and he ran into a mentor of mine,” she explains. “They said, ‘I’m looking for a lawyer in the Governor’s legal office. Somebody who has varied experience and is mature’ – whatever that meant at the time. But my mentor thought of me, and now I’m forever grateful for whatever they were drinking at that cocktail party that led to me being hired in 2000!”
Working at the Governor’s legal office was and is “really a gift” for a lawyer. Covering an “array of subject matters,” Judd-Stein encountered numerous issues of “real interest” to her, as well as becoming acquainted with the Massachusetts State Constitution. Her role covered subjects ranging from transportation to health, to human services and education. She then became Governor Celucci’s ethics advisor “by default.” Here, she was able to “add value in a unique way.” Even if that value wasn’t commercial, expertise was developed that aided government officials and state employees – leading to Judd-Stein being kept on and, ultimately, serving several different governors within the state.
Succeeding Cellucci were Governor Jane Swift, Governor Mitt Romney and Governor Deval Patrick, the latter of which Judd-Stein served as both his Deputy Legal Counsel and Judicial Nominating Commission Executive Director. After this eight-year period, Judd-Stein decided to leave the Governor’s office. She served for a time within the state’s highest court then was asked to join the Massachusetts State Lottery. This is where gaming would become prominent within her career for the first time (although most certainly not the last).
In it to win it: The State Lottery
It was the month of May 2011 that saw Judd-Stein appointed Assistant Executive Director, and Director of Policy and Special Counsel, at the Massachusetts State Lottery Commission. She joined just as the Bay State’s expanded gaming law was passed, with State Treasurer Steven Grossman and Executive Director Paul Sternberg asking Judd-Stein to help the Commission develop its licensing process for casinos. Indeed, the expanded gaming law prioritised the Massachusetts State Lottery – under the purview of the State Treasurer – and the state wanted to avoid the cannibalisation of lottery through casino play. On top of that, Judd-Stein was involved in starting Treasurer Grossman’s taskforce on iLottery – a topic still pertinent today. Currently, Massachusetts State Treasurer Deborah Goldberg is still seeking the legalisation of iLottery, which leads on from the initiation of that very taskforce. Back then, Treasurer Grossman did not take a stance on the matter, but wanted the research conducted even though he did not eventually pursue it. Either way, the ball was now rolling and that process continues today.
As for Judd-Stein herself, it is no longer an issue she deals with as a member of the State Lottery Commission, rather now as the Chair of the Massachusetts Gaming Commission. There was, of course, the small matter of six years between those two roles, as she spent over a year as General Counsel for the Treasury – and was then “really lucky” to spend four years as the Deputy Chief Legal Counsel for Governor Charlie Baker, the fifth governor Judd-Stein would serve under. It was Baker who then approached her about joining the Gaming Commission, cementing her firmly within the world of gambling once more.
A “common thread” that weaved through her career, according to Judd-Stein, was that she worked for Governors who valued “integrity, transparency and fidelity to the law.” These aspects are “critical” to any regulatory role, in Judd-Stein’s view, preparing her for the role of Chair, where she is pleased to have played her part in important decisions that impact both public and private issues. As Chair, she is also buoyed by the belief that the expansion of gaming has generated benefits for the Massachusetts Commonwealth. This equally applies to the legalisation of sports betting in August 2022 (before launch in January 2023 and mobile gaming following in March 2023). It is inevitable that gaming brings revenue as an economic driver, but Judd-Stein does not believe this to be the priority for legislators. She adds: “I like to think the Gaming Commission’s allegiance is really with things like consumer protections, strong advertising regulations, the enforcement of internal controls and regulation that you need to preserve and enhance integrity.”
We all said our prayers when we had to conduct our first public virtual meeting, which was when we actually had to shut down operations. And ever since then, we have been reading boxes, conducting our meetings publicly and streaming them publicly
Diversity, equality and inclusion
In the Chair’s eyes, Massachusetts is at the “forefront of the responsible gaming conversation” and Judd-Stein loves the influence she has on the state’s licensees on this front. She tells Gambling Insider:
“To be clear, we’re really lucky to have very cooperative licensees, but I have to say perhaps the most rewarding and unexpected benefit in terms of our sports wagering licences hit recently. Massachusetts asks a lot of our licensees. We are a very active group of regulators. We are innovative in our application process and we prioritise consumer protection and advertising. But we are also working with intentionality around diversity, equity and inclusion (DEI) – which are very important in Massachusetts, and in our nationwide dialogue.”
Judd-Stein is impressed with how each licensee within the Bay State has “stepped up to the plate,” developing DEI benchmarks they didn’t previously have. Giving a particular “shout out,” Judd-Stein cites the Boston Globe’s announcement that DraftKings was named one of Massachusetts’ top 10 large employers – but also that it was designated as a 2023 DEI Champion. “I’d like to think we might have pushed that needle a little bit,” she reflects. “So I would say as much as I’m very interested in making sure the gaming industry in Massachusetts has a sustained model of integrity and offers all the consumer protections, it’s those unexpected benefits of this job that I’m really enjoying.”
Zooming in
Judd-Stein began her role as Chair of the Gaming Commission in February 2019. Some quick arithmetic tells you that gave her roughly 12 months before the Covid-19 pandemic began to permeate lives across the globe. For billions, this not just disrupted but transformed company practices on a temporary basis; but for Judd-Stein and the Commission, the Zoom culture that was thrust upon them has actually remained a permanent feature of Massachusetts life. “It was an interesting development and we were lucky that we were able to anticipate a pandemic from the CEOs coming out of Las Vegas – who were already looking at Asia,” she looks back.“We’re required to do all of our meetings in public and we were doing them all in person, so we anticipated that something was going to have to shift. I did get in touch with the Governor’s office saying we might need to have some relief here to conduct our business virtually. Apparently there was one other big public body – bigger in terms of number of employees and scope of business – that also approached Governor Baker and, under an emergency procedure, he issued an executive order that gave us that relief to start doing virtual meetings.”
“Our IT team immediately got us organized and we all needed some training,” the Chair continues.“We all said our prayers when we had to conduct our first public virtual meeting, which was when we actually had to shut down operations. And ever since then, we have been reading boxes, conducting our meetings publicly and streaming them publicly. We’re committed to transparency by law. The law requires us to make sure the public has access to our agenda and our meetings. We record everything and, since Covid we have conducted pretty much every meeting in public, with a few exceptions. We were just out in Springfield and we had an in-person meeting that also had some virtual capacity; and we conducted one roundtable while standing up sports wagering at the statehouse, to understand the landscape of interest that was conducted in person. That was very effective.”
As Judd-Stein rightly points out, our own conversation is taking place across Zoom and the online platform allows for a greater overall level of participation at the Commission’s meetings. The obvious advantages extend to attendees who might otherwise be engaged, with Judd-Stein explaining that it allowed the participation of so many different parties, from responsible gaming researchers to representatives from the MLB Players Association. They used to join via phone – but it was less effective. Commissioners now have increased flexibility and, while an in-person capacity is being worked on, the virtual element has been “highly efficient and super participatory.”
Seeing staff shine
When Gambling Insider tells Judd-Stein we have attended a fair few of those virtual meetings ourselves, and can therefore vouch for their 100% public transparency and availability, Judd-Stein quips: “I’m so sorry!” While she reemphasises the desire to do more in person, the Chair is also pleased the occasional animal guest – such as Mango the cat – helps add a fun side to the meetings. Yet, on a more serious note, these meetings also present a fantastic opportunity for the Massachusetts Gaming Commission’s younger members of staff, whether virtual or in person. In fact, this leads us to Judd-Stein’s “favourite thing about being Chair.”
“It’s when I am conducting a public meeting or working with members of staff, and see our younger employees and newer team members shine,” she beams.“We have a great team. They have really good mentors and superiors. We have an opportunity for growth in the organisation and I’ve witnessed it. I’ve worked with some of those younger or newer employees, and now they’ve got big roles. I like seeing that and I forget – because us Commissioners are so used to appearing in these virtual meetings that I have to just forget they’re public; and that they may be attended by members of the press, et cetera. To see our team members present complex matters and have to deal with our sometimes pretty thorny questions on the fly; it’s not lost on me how difficult that is – and I’m super proud of them.”
However, an issue that constantly challenges Judd-Stein – and any gaming regulator for that matter – is how to combat the black market. Regulators cannot physically stop illegal, unregulated operators, meaning the best Judd-Stein, the Commission and others can manage is to partner with law enforcement officials, and “really encourage how best the tactics we use can shut those businesses down.” But it is not easy. The Chair is keen to emphasise that, particularly within sports wagering, the Commission has been organised, well-coordinated and, importantly, flexible.
Something she has said to Gambling Insider on more than one occasion is that a regulator must stay nimble. Again, this is not easy.
A good cup of coffee, some dark chocolate and a conversation with my dog also keep me in the game
Regulation and cooperation
In fact, ensuring your regulations actually work in practice – not just on paper – is one of the hardest things about being a regulator, according to Judd-Stein. Due to the inherent culture of Massachusetts as a state, “a lot” is expected of its licensees. There is a desire to be fair, but it is matched by a statewide desire to be “rigorous.” The Chair feels like licensees are asked to “jump through hoops” – but her “biggest frustration” does not come from their reluctance to do so. Indeed, Judd-Stein’s frustration stems from the fact they are all doing what is asked of them – “and they’re doing it well.” But that only encumbers the DraftKings, FanDuels and MGMs of the world – the operators actively taking part in the regulated market – when unregulated and unlicensed entities do not follow the same rules. “It’s an unequal playing ground,” Judd-Stein remarks. “It’s an issue that frustrates me, but we’re working on it.”
From frustration to “guilt,” Gambling Insider is surprised to hear the ever-positive Judd-Stein list a second consecutive negative emotion. But her reasoning is true to her gracious self as she explains why: “I feel guilty sometimes because I know that, with Massachusetts being in the more nascent entry point for expanded gaming and sports wagering, I, my fellow commissioners and all of our staff members, have relied on the expertise and the generosity of other regulators. That level of collaboration and cooperation is absolutely vital for us to be successful.” Occasionally, the Chair says, the Massachusetts Gaming Commission is able to give back, but she acknowledges the body is more of a receiver than a giver in this area.
But this requirement for collaboration extends beyond just regulator-to-regulator relations, too. Judd-Stein explains: “It is key not only among us regulators, but even between licensees and regulators. Because I think we’re all trying to make sure the industry is safe for patrons and for employees. It reminds me how young America is when I go to Europe. When I’m in a room full of regulators, like I was at the Regulating the Game conference recently in London, I am reminded about how new we are to this industry and how grateful we are for everybody’s generosity.”
Beyond the Boardroom
The culmination of all this cooperation, and the Commission and Judd-Stein’s work in Massachusetts, has been the creation of a market that generated $143m in total gaming revenue for November 2023. In total, $48.9m of this figure came from sports betting, while all-sources revenue accumulated a total $36.1m in monthly tax revenue. After legalisation, Massachusetts’ sports wagering sector took just six months to launch. To meet that timeframe, the Commission “learned all perspectives,” convened around 150 public meetings and worked “incredibly hard” to form a sector with “the strongest of consumer protections” while, at the same time, being “grounded in integrity.”
There is life beyond legal duties for the Chair, though, as she admits “the outside world is a lot more fun than some of our meetings!” Judd-Stein feels she is “really fortunate” to have been able to navigate her work-life balance. Wise words from a mentor once helped create a sense of perspective. “She once saw me working hard at my job and also raising three kids close in age,” Judd-Stein explains. “She said to me: ‘If you allow your family to be your priority, you’ll always make great choices around your career.’ I’d say, given the career path I’ve had, it’s been so varied that it’s worked out. But anybody who knows me really well knows that it’s my husband, my three adult kids, my two perfect toddler grandsons, and all my friends who I look to for support; and to inform me about my choices and priorities.”
Outside of the ‘day job,’ Judd-Stein sits on certain nonprofit boards that focus on education, particularly within the sphere of secondary education. As she demonstrated earlier in the interview, she is “very committed” to working on gender equality issues. This extends to the delivery of healthcare, ensuring both women and men are treated alike. Family and “the little things in life” give Judd-Stein the kind of balance in her personal life she is constantly striving for within Massachusetts’ gambling landscape. But, while those most important to Judd-Stein help keep her balanced, she adds that “a good cup of coffee, some dark chocolate and a conversation with my dog, Mojo, also keep me in the game.”
The Chair is “lucky enough to still embrace the outdoors” through skiing, hiking and even paddleboarding, kayaking and water skiing. “That’s where I flourish,” she smiles. Although, after a career serving five different Governors and contributing her fair share to US gaming, it’s fair to say Judd-Stein has also flourished on her legal and regulatory journey. Humbly, however, she will no doubt credit the role of the team and staff around her for any success to come.
