Former Tax Board Chair Jailed for Misappropriation of $49k to Fund Casino Habits


Cheryl S. Sullivan, age 69, formerly the chairperson of the Dedham, Massachusetts Board of Tax Assessors, was sentenced to three years probation last week, after being found guilty for wire fraud. The merit of Sullivan’s case emerged on the grounds of misappropriation of funds from the River Island Condominium Association in Woonsocket, Rhode Island, which amounted to a substantial total of $49,156.

Thrown into the swirling vortex of greed, Sullivan used this stolen money to cover her personal expenses and recurrent visits to the Plainridge Park Casino in Plainville, Massachusetts. Reports confirmed that Sullivan used her association’s debit card 58 times to extract cash directly from ATMs in the casino between January and November 2019. This illicit use of the condo association’s debit card only began after her personal debit card was rejected.

Repeated trips to the infamous casino were so frequent that Sullivan gambled there 176 times within an 11 month timeframe in 2019. Though conflicting accounts exist about her potentially gambling away the misappropriated funds at the casino or utilizing them for other expenses, Sullivan managed to repay approximately half of the stolen money back to the condo association.

Penn Entertainment operates the Plainridge Park Casino, a property owned by Gaming and Leisure Properties. Located around 35 miles south of Boston, Plainridge remains one of just three full-service casinos within the state of Massachusetts.

Later, on January 31, 2022, Sullivan was arrested and was seen first in Providence, a Rhode Island federal court, on five counts of wire fraud. She originally pleaded not guilty to all the charges but later agreed to a plea deal which led to lesser charges.

A thorough review of Sullivan’s case fleshed out her history as a property manager at the condominium, her notable experience as a real estate broker and tax preparer, and her role as a chairperson of the Dedham Board of Tax Assessors. Notably, Sullivan had a clean criminal record prior to this case, a factor that contributed significantly to her receiving probation as a final sentence rather than a more stringent penalty.

Thus, as this story illustrates, the allure of gambling can often lead individuals down a murky path. Interested in learning more about responsible gaming? We at the West Island Blog regularly update our site with the top online casinos of the month and valuable insights into safe online gambling practices. Make sure to check back often for the most recent information and advice.