Courtesy of Zach Chernak

Handsome Dan XVIII may be retiring in early spring, but his presence has multiplied around New Haven in recent weeks: Two large canvas paintings of Yale’s mascot have surfaced on Broadway and Chapel streets.

Both pieces were painted by local artist Zach Chernak, one of several painters invited by The Shops at Yale to create art inspired by New Haven after the original mural contest on Broadway Island planned for August was canceled due to COVID-19.

The artists, each of whom received a small stipend for supplies, were asked to create murals with the theme of New Haven in mind. Chernak chose to combine two hallmarks of the city, pizza and Yale’s beloved mascot Handsome Dan, in his painting. The Shops at Yale then directly commissioned him to paint another Handsome Dan portrait — this time with ice cream — after seeing the first.

“What are the first two things that come to mind when you think of New Haven? For me, that’s pizza and Yale,” Chernak said. “I think it’s a really fun concept that The Shops at Yale liked.”

Courtesy of Zach Chernak

During late October and early November, Chernak used house paint to create the 8-foot-by-4-foot wood canvas painting of Handsome Dan holding a slice of pizza in his mouth. The piece is currently displayed on Broadway, though Chernak said he was not sure how long the piece will remain installed.

David DelVecchio, the director of real estate asset management at Yale, praised Chernak’s work and explained how The Shops at Yale commissioned Chernak’s second painting.

“We loved Zach’s concept of Handsome Dan eating pizza so much that we asked him to paint one of Handsome Dan eating ice cream as well,” DelVecchio wrote in an email to the News. “They came out great. Zach is a terrific artist.”

Courtesy of Zach Chernak

Chernak said both pieces took a total of about 20 hours to complete, far longer than the original allotted time of four hours. Although he only got paid for the four hours, Chernak said he was more than happy to do the work and came back to the piece over a number of weekends to complete it.

Chernak, who lives in Naugatuck, Connecticut, said his love for art blossomed at a young age.

“I’ve been doing art as long as I can remember,” Chernak said. “Growing up, instead of having my mom reading me books, she would draw pictures for me at night.”

He continued to pursue that passion and decided to make a career out of it by attending school for art education. Now, Chernak works at Cooperative Arts & Humanities High School in downtown New Haven, where he has taught visual arts for ten years.

In addition to teaching, Chernak is an active artist in New Haven. He participated in the New Haven Chalk Art Festival in 2018, drawing a portrait of Frankenstein on Broadway Island.

His continued contribution to art in New Haven has drawn recognition from passersby — and even from Handsome Dan XVIII himself. After the pieces were put on display, Chernak said he received direct messages on Instagram from Yale’s Director of Athletics Vicky Chun and the Handsome Dan XVIII Instagram account, which has more than 30,000 followers.

“His artwork made [and] makes me instantly smile in a time where there hasn’t been much to smile about,” Chun wrote in an email to the News. “I’m sure I’m not alone in this. It’s a great reminder to all of us that Yale is an awesome place…with great pizza, ice cream and athletic teams.” 

Chernak’s painting of Handsome Dan with pizza is currently displayed next to L.L. Bean at 272 Elm St., while his piece of Handsome Dan with ice cream is at 1022 Chapel St.

According to DelVecchio, The Shops at Yale plans to do similar projects in spring 2021.

Veronica Lee |

Veronica Lee covers breakthrough research for SciTech. She is a sophomore in Branford College majoring in molecular, cellular, and developmental biology.