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Beloved Deputy Town Supervisor In Westchester Dies: 'Quiet, Strong, Real, Solid'

A beloved former town employee, husband, and father from Northern Westchester is being remembered for his ever-caring nature despite his stoic outward appearance. 

Leo Masterson of Cross River died on Thursday, August 24.

Leo Masterson of Cross River died on Thursday, August 24.

Photo Credit: Oelker-Cox & Sinatra Funeral Home

Leo P. Masterson of Cross River, who worked as Comptroller and Deputy Town Supervisor for the town of Lewisboro, died on Thursday, Aug. 24 at the age of 66 after an 11-month battle with peritoneal mesothelioma, according to his obituary. 

Born on Staten Island in 1957, Masterson was both a standout student and athlete and played football and baseball in high school. He then went on to continue playing baseball during his time at Wagner College, where he earned an accounting degree. 

Masterson then became a CPA and earned his Master of Business Administration at St. John's University in Queens. 

After college, Masterson began working for Shell Oil Company in New York City, where he met his wife and the love of his life, Lori, whom he married in 1988. The two then began their family in Katonah before moving to Cross River. 

Known for his devotion to his work, Masterson eventually became the Chief Financial Officer, Vice President, and Treasurer of the Private Export Funding Corporation in New York City for two decades. 

He was then able to secure the position of Comptroller in his hometown of Lewisboro, where he met Town Supervisor Tony Gonçalves, who memorialized Masterson in a post on social media following his death. 

"The Town of Lewisboro has lost one of its greatest assets and he will be deeply missed by all who benefitted from his tremendous work ethic, financial acumen, inherent decency, and marvelous sense of humor," Gonçalves said, adding that he appointed Masterson as Deputy Town Supervisor in January 2022. 

At the end of that year though, Masterson stepped away to focus on his health. Even during his battle with mesothelioma though, he offered his help and time to the town, Gonçalves said. 

"Leo had to focus on his health but was still able to dedicate time to help me with our Town's 2023 budget, including understanding all the intricacies of municipal finances," Gonçalves said, adding that he last saw Masterson in late June when he came to help the town's new Comptroller. 

"I was hoping we would see more of Leo but God had other plans for this great man," Gonçalves continued. 

In addition to his work with the town, Masterson also enjoyed coaching his children's sports games and vacationing with Lori. He was known for not always sharing his feelings on the outside, but instead showing his love for people through his actions, according to his obituary. 

"Quiet but strong, real, and solid. Leo's caring heart shines through how he treated others with his actions, in big and little ways, every day," his obituary said. 

Masterson is survived by Lori; his children, Andrew and Sara; their dog, Zulu; and his two sisters, Lynn and Eileen. 

A service for Masterson will be held on Wednesday, Aug. 30 from 4 p.m. to 8 p.m. at the Oelker-Cox & Sinatra Funeral Home in Mount Kisco at 262 Main St. 

A funeral mass will then be held on Thursday, Aug. 31 at 11:30 a.m. at St. Joseph's Church in Somers at 95 Plum Brook Rd. 

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