Top 5 Most Influential People in Massachusetts Gaming

Written By Dan Holmes on October 5, 2023
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The Massachusetts gaming industry is unlike any other jurisdiction in the country. That’s a good thing. Massachusetts has traveled a thorough and methodical path to building a well-regulated, responsible, and prosperous market.

Some observers of the Bay State may feel the state moved too slowly. Or that the Massachusetts Gaming Commission has excessive focus on on hyperregulation. But, the results can’t be quibbled with.

States across the country have followed its lead. Brick-and-mortar casino owners and online sportsbook licensees alike, are satisfied with a fair and fast-growing gaming market in the Commonwealth.

This doesn’t happen by accident. The state is led by several individuals who have helped shaped Massachusetts gaming into what it has become. Although there are no Massachusetts online casinos yet, there are three vibrant brick-and-mortar properties and several Massachusetts sports betting options.

Here’s a look at who PlayMA believes are the top five most influential people in Massachusetts gaming.

Honorable Mention: Crystal Beauchemin

Beauchemin is the MGC’s sports wagering business manager. She didn’t crack the list this go-around. However, she was recognized as an emerging leader in the gaming industry and will be honored at the Global Gaming Expo in Las Vegas.

Her opinions seem destined to shape the Bay State’s gaming industry in the future.

5. Caitlin Monahan – deputy general counsel at Massachusetts Gaming Commission

Unless you’ve observed the workings of the MGC, you won’t recognize Caitlin Monahan’s name. She is a two-plus-year veteran of the MGC’s legal counsel. But Monahan in many ways serves as the legal bulldog for the regulatory body.

Time and again during public meetings, it falls on Monahan to deliver the expertise the MGC needs to understand the gaming laws and responsible gambling implications, and craft a strategy for the commission to deal with the work of the state.

Monahan is the most no-nonsense, by-the-book figure in MGC meetings. She is ever-vigilant and precise with the words and counsel she supplies to commissioners who are often overloaded with tasks and information. Or just plain confused.

4. Jenny Holaday – president of Encore Boston Harbor

The largest and most modern casino in the state, Encore Boston Harbor, has been a success since its 2019 opening. The casino resort employs in excess of 2,000 people, most of them Massachusetts residents. As president of the Wynn’s only non-Vegas U.S. property, Jenny Holaday is responsible for overseeing the entire operation.

Encore has transformed its home city of Everett. While a few hiccups have occurred, such as labor disputes and traffic issues, it has been a boon to the economy. It also sends tens of millions of dollars in tax revenue to the state.

With nearly 15 years of experience in casino/resort management, Holaday has proven her resilience in an often male-dominated industry. Encore Boston Harbor is the largest casino in the nation with a female president, and under her guidance, the organization is making positive contributions. One of her noteworthy initiatives is to donate over 1 million meals to food banks in the state.

3. Bruce Band – director of sports wagering at MGC

Every organization needs leadership. They need vision. They also need the lawyers (who else is going to slow everything down?). But organizations also need the people who get things done in the trenches.

For the MGC, that’s Bruce Band. As director of sports wagering, he leads the commonwealth’s day-to-day efforts of overseeing and operating the gaming industry. Whether it’s lottery, casinos, online sports betting, licensing, or an investigative job, Band is at the forefront for the commission.

Band is praised by his peers and colleagues, and brings more than four decades of experience in gaming to his current role. He’s worked both in the private sector, and on the regulatory side. His expertise in the investigative and enforcement side serves the commonwealth quite well. He is fair-handed, but tough, and always willing to let those who work under him shine.

2. Jason Robins – CEO of DraftKings

DraftKings Massachusetts is not only one of eight online sportsbooks in the state; its headquarters are less than a mile-and-a-half from the offices of the MGC.

The influence from this Boston-based gaming behemoth cannot be overstated. Since Robins controls that company, that makes him a powerful man in the Massachusetts gaming world.

When Massachusetts lawmakers debated sports betting legislation, Robins lobbied on behalf of the industry. He was included when Speaker of the Massachusetts House of Representatives Ronald Mariano held hearings to discuss versions of a sports betting bill for the commonwealth.

Bostoners and Massachusetts folks love to support their own. DraftKings is practically as synonymous with Boston as Fenway Park. As long as Boston-native Robins leads DraftKings, he will be a major force in gaming in the state.

1. Todd Grossman – interim executive director and general counsel, MGC

With apologies to the public at large, we have a second attorney on this list. But Todd Grossman’s influence is too large to ignore.

The MGC employed Grossman in some capacity for more than a decade. But he served the commonwealth for longer than that in various jobs. Currently, he’s filling the executive director position on an interim basis after being unanimously selected by the commission. It’s unclear whether he is in the running for the permanent position.

Grossman is a classic lawyer in public meetings. He is measured and unexcitable, while careful to mediate and build a consensus. It’s clear that his advice, drawing on years of experience in gaming, carries immeasurable weight on every topic he’s asked to weigh in on.

His legal work formed the foundation for the Massachusetts’ regulatory framework for the sports betting launch last January.

As a Massachusetts native who received his law degree from New England Law School, he is the favorite to fill the role on a permanent basis. The hiring committee should complete its search later this year or early in 2024.

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Dan Holmes

Dan Holmes is a Staff Writer for PlayMA with plenty of experience under his belt. Dan has written three books about sports and previously worked for the National Baseball Hall of Fame and Major League Baseball. He also has extensive experience covering the launch of sports betting in other states, including Ohio and Maryland. Currently, Dan is residing in Michigan with his family.

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