The Westport Police Department announces the retirement of Deputy Chief Vincent “Vinny” Penna October 1 st . Deputy Chief Penna was hired in 1991 as a traffic agent and later entered the police academy as a special officer. He became a regular full-time officer in 1994 and worked his way through the ranks to Deputy Chief. He led a commendable and exemplary 26+ year career, over the course of which he received numerous commendations, awards and accolades. He served as the president of the Westport Police Union for 4 years and President of the Westport Police Benevolent Association for the same. Additionally, he was a member of the SWAT team before it became a regionalized unit.
Deputy Chief Penna is a graduate of Quinnipiac University where he earned a Bachelor’s of Science degree in Management. Deputy Chief Penna, like all Westport officers, started his career assigned to patrol. He moved up through the ranks gaining promotions to detective in 2001 and sergeant in 2006. In 2009, Penna returned to the detective bureau, which he commanded as a lieutenant and captain until his promotion to deputy chief in 2016. As Deputy Chief, Penna commanded the operations division of the police department, which oversaw the patrol division and investigations. He later became the professional standards commander overseeing Westport EMS, building maintenance, internal affairs, public affairs, animal control, the training division and information management.
Deputy Chief Penna is credited with seeing the department’s tedious accreditation application process to fruition and successfully acquiring Tier 1 accreditation. Only 40 agencies in the state hold the distinction of
accreditation. First Selectman Jim Marpe stated, “Deputy Chief Penna has served his department and the Town of Westport well for the last 23 years.We are grateful for his long commitment and dedication to the town. We wish him well in his retirement and continued success in all his endeavors.”

Chief Foti Koskinas added to the sentiment, “Deputy Chief Penna takes with him a great deal of experience and knowledge. We worked together for many years. We came up through the ranks together, navigated through difficult times and shared countless laughs. He’ll certainly be missed by the men and women that worked with him. We all wish him the best in his retirement.”

Deputy Chief Penna also reflected on his career, “I’ve had a great career over the last 24 + years. I’ve been fortunate enough to have the opportunity to either work in or supervise almost every division of the department.  Some of my assignments have afforded me the opportunity to leave enduring changes on the agency which will be present beyond my tenure, including assisting in the revision of the departments general orders through the accreditation process and the inclusion of the department in Norwalk’s juvenile review board, which affords our youth an alternative to being charged criminally if they meet certain criteria. I feel fortunate to have been able to work in the town I grew up in with the best men and women in law enforcement and can honestly say I’ve enjoyed coming to work every day.”
The vacancy left by Deputy Chief Penna’s retirement will be filled by a restructuring of the police department organization and promotion of Lieutenants David Farrell and Ryan Paulsson to the rank of captain.