He’s Quite a Character

by Jill Duff-Hoppes

When Officer Leo Massip joined Oviedo Police Department’s community involvement division in late 2024, he wanted to color outside the lines.

The Police Department often sets up a booth at community events to educate the public, hand out giveaways, and provide opportunities for officers and residents to get to know one another. Leo wanted to add a little more pizzazz to those interactions, so he began brainstorming for ways to do just that.

“My main goal was to create new events – something that would engage the public, something different,” says the 39-year-old Leo, who was hired by the Oviedo Police Department in 2017 as a road patrol officer.

To achieve his goal of something new, Leo drew on his past – literally. A lifelong artist, he decided to offer free drawing lessons at community events. Leo’s first appearance was in 2025 at an area art festival, where he set up shop wearing his police uniform, with art supplies in hand.

“This one kid sat down in front of me, and I said, ‘Hey, how are you today? You want me to teach you how to draw?,” recalls Leo. “And he said, ‘No, I want you to draw me.’”

Leo obliged, whipping out a caricature of the boy. Passersby took notice, and soon enough, festivalgoers of all ages wanted Leo to draw them, too.

“They usually take a peek and say, ‘Oh, that looks cool. I want to do it.’ The line was so crazy long; it was hours and hours of drawing people,” remembers Leo. “It’s been a success ever since.”

Over the past year, Leo has offered free caricatures at several community events in Oviedo, including Cops ‘N Cars for Kids, Taste of Oviedo, the city’s 100-year anniversary, National Night Out, Oktoberfest, and Winterfest.

Art for the Dogs

Unlike a portrait, a caricature is not a realistic rendering of a person. Rather, it’s a quick drawing that exaggerates a person’s most distinctive features, usually for comic effect. One of Leo’s favorite events for caricature work to date has been Bark and Brew, Oviedo’s signature craft beer and canine festival. Leo got quite a kick out of drawing dog lovers with their four-legged companions.

“It was funny,” he says. “I was giving these pets a whole lot of personality. My favorite pet to draw is the chihuahua. They’re all ears, and their faces are just so adorable.”

Leo’s interest in drawing goes back to his childhood in Cuba, where he was born and raised. Except for a short stint at an art school, Leo is self-taught and draws by hand on paper and digitally on a tablet. Growing up, he was fascinated with cartoons, particularly anime (Japanese animation), and he drew every day as a youngster.

“I was never interested in painting realistically,” says Leo, who drew his own characters in the anime style. “It was always cartoons. It was always fantasy.”

After moving to the United States in 2008, Leo worked in the pest control industry before shifting to a career in law enforcement at the age of 30. Married with five children, Leo no longer has much time to create his own personal artwork. That’s one of the reasons he enjoys drawing caricatures at local events – it gives him a chance to flex his artistic muscles.

“I get to make fun of people for free,” Leo says with a smile. “And people get a laugh and a good memory. We talk, and it’s fun.”

A People Person

While he’s drawing, Leo often scans the line of folks waiting for their turn and gets them hyped up with a joke or two.

“’Oooh, you’re very drawable. I can’t wait for you,’” Leo will say. “For couples, I go all out. I see certain things that I’m going to enhance to make them unique. I make it super funny without making them unrecognizable.”

When people watch Leo at the drawing board, the first thing they usually ask is whether he uses his artistic skills for official police business, like sketching crime suspects. The answer is no.

According to Lieutenant Adam Egert, the department’s public information officer, “We do not do suspect composite drawings. That involves additional training and certifications, but due to technology, it is seldom needed anymore.”

When Leo is drawing at community events, he sees lots of kids who might have an interest in art, just like he did. He wants those aspiring young artists to know they can be creative, too – and without breaking the bank. For his caricatures, Leo uses simple, affordable supplies: pencils, colored pencils, markers, ballpoint pens, and paper.

“You don’t need fancy stuff,” he says. “I don’t use anything crazy, and I have a good time.”

You’re Up!

Leo is planning to draw caricatures at a couple of Oviedo’s biggest events this spring, including the St. Patrick’s Day Celebration and the Egg-Ceptional Family Festival, both in March at Center Lake Park. If you’d like Leo to capture a comical likeness of you, be sure to look for him at the Oviedo Police Department booth. Stop by, say hello, and sit down to be immortalized by Officer Massip.