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News  Probation Officers engage with community at 52nd Annual Boston Caribbean Carnival, make cameo appearances in viral video

Suffolk County Probation Officers have attended the Boston Caribbean Carnival for more than two decades where they interact with members of the community and assist Boston Police with crowd control.
9/02/2025
  • Massachusetts Probation Service

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Coria Holland, Communications Director

A group of 6 probation officers pose together

Left to right: BMC Roxbury PO Wendy Pena, Suffolk Juvenile ACPO Sherry Cobb, BMC-Roxbury ACPO Keison Harry, Suffolk Superior PO Kendall Bruce, Suffolk Superior PO Cherill Roberts,
Middle: BMC-Roxbury PO Yasira Montas.

The Probation staff from Suffolk Superior, Suffolk Juvenile, and the Roxbury Division of the Boston Municipal Court engaged with the community and made a cameo appearance in a viral video featuring Boston Police Officers swaying to the beat of Caribbean music at Boston’s 52nd Annual Caribbean Carnival.

Each year, the carnival attracts between 500,000 and 800,000 people, according to the Boston Caribbean Carnival website. The Carnival features colorful costumes, music, and food to celebrate Caribbean heritage and culture.

Representing MPS at the Boston Carnival were Keison Harry, BMC-Roxbury Assistant Chief Probation Officer; Wendy Pena, BMC-Roxbury PO; Sherry Cobb, Suffolk Juvenile ACPO; Kendall Bruce, Suffolk Superior PO; Cherill St. Louis, Suffolk Superior PO; and Yasira Montas, BMC-Roxbury PO. 

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  • Massachusetts Probation Service 

    MPS's main goal is to keep communities safe and to provide people on probation with the rehabilitative tools they need to live a productive and law-abiding life.
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