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Lauren Valdario and Giacomo Cantoni share two very important things — both are Winchester natives and both are working at their dream jobs.
On a sunny spring morning, both Valdario and Cantoni sat down to talk about what it’s like to work as police officers in the same community where they grew up.
“I like it,” said Valdario, a sergeant with the department. “I like that I’m giving back to the town I grew up in. I’ve had positive interactions with people in the community, even with the same people I grew up with. Getting good results is all in how you handle things.”
Valdario is one of four women on the Winchester Police Department. She was hired in 2019 after taking the Civil Service exam and attended the academy in January 2020, just months before COVID-19 hit.
“Everything was locked down,” she recalled of the pandemic. “We were already there so we were able to get a lot done. Then we did things online. The academy is usually six months, but we were there for about seven.”
Valdario started in the patrol division in 2020, where she worked on the day shift for two years. Then she was promoted to detective in September 2022, where she stayed for another two years. In September 2024, she was promoted to rank of sergeant after taking that exam.
“I really enjoyed being a detective, but I wanted to advance in my career,” Valdario said, of why she took the test. “That was the next step for promotion.”
She is currently the only one of the four female officers to hold a rank position.
With the promotion came another change for Valdario — a new job as School Resource Officer (SRO) at the McCall Middle School, as well as all the elementary schools, and as community resource officer.
Valdario said working at the different schools is challenging. At the elementary level, she said, it’s a matter of building relationships with the kids and having them see her as someone they can go to if they’re in trouble. The middle school, she added, is a different job because the students are older and have other issues.
“I like working with the kids so it’s a good experience,” Valdario said, of the job.
And she plans to stay in the position.
“I am going to stay in this role for a bit,” Valdario said. “I do want to look at advancing, maybe taking the lieutenant’s exam. But, I want to take this role on for a while.”
Fresh from the academy
In early April, Cantoni was just six weeks into the job. He had entered the academy in August 2024 and just graduated February 2025.
“I loved it,” he said, of the academy. “I met a lot of great people. It was like hanging out with 40 of your best friends every day for six months. I have friendships all through the area.”
His first day on the job was a bit surreal.
“I was very nervous,” he said. “I sort of couldn’t believe it.”
The first week was filling out paperwork, nothing Cantoni would call exciting. But he loved being out in Winchester with his training officer.
“My first day on the street was fun,” he said. “I can say it was a special moment for me to be in a uniform that I’m going to wear for the next 20 or 30 years.”
As of April, Cantoni had two field training officers to show him the ropes. He was scheduled to be in training for a total of eight weeks and on patrol by himself in June.
“I’ve already learned so much and they’re doing a great job of teaching me the basics,” Cantoni said. “I know it’s going to be a while before I get a good grip on things, but I know I’m in a good department and that they will back me up when I need help. I know I can always call on them.”
Everything is just so brand new.
“It’s exciting,” he said. “I know it’s all routine for the guys on the road, but for me it’s all so new.”
Things in common
Both Valdario and Cantoni have more than just being Winchester natives in common. They have both wanted to be police officers since they were kids.
“I wanted to help people,” Vadario said, of why she picked law enforcement. “I listened to my uncle’s stories and I felt like this was the right profession for me.”
Valdario’s uncle is a police officer in Naples, Fla. She said her family has always been supportive of her choice to be a cop.
Cantoni is the first in his family in the field. He said his family is also supportive.
“It took a while for my mom to come to terms with it because of the dangers that come with the job,” he said. “But now they like it.”
Cantoni added Winchester was his first choice after graduation and he’s happy to be on the department.
“I always wanted to be a police officers as far back as I can remember,” he said. “I wanted something that wasn’t routine, that was different every day, where I could help people and be out working with them. Policing was for me.”
When asked where they see themselves in the future, Cantoni shrugged.
“I’m green, so for me it’s one step at a time,” he said. “I have to focus on the things I need to learn so I’m just taking everything in. I’m gaining confidence and I can’t wait to be out on patrol.”
And Valdario? Does she have her eye on being Winchester’s first woman police chief?
“Not right now,” she said, with a long laugh. “I love this job and I find it really rewarding. I love working with kids. It’s pretty awesome.”
