Simon Yu (center, behind bar), owner of Simon’s Coffee Shop, at work on a recent day in Dec. 2025.
Prapti Sekhon and Diego Lasso are two of the many regulars at Simon’s Coffee Shop. They meet there every other day, trading stories, life updates and advice over a small table and a few cups of coffee.
Lasso, 67, known as the “mayor” of Simon’s, travels from Roxbury to Simon’s every day to read the newspaper – yet he rarely gets to it, interrupted by conversations with other customers. Sekhon, 31, intentionally signed a lease on an apartment based on its proximity to the coffee shop.
Simon’s and the community around it have become part of their routine.
Yet a new development project could displace Simon’s and the other businesses at 1740 Massachusetts Ave., which include Keezer’s & Le Couturier House of Alterations and a Walgreens. Developers plan to demolish the one-story building there next summer or fall and spend 18 to 20 months constructing a six-story, 71-unit mixed-use building.
Simon’s Coffee Shop was founded in 2002 by Simon Yu, who bought a former coffee house, renamed it and focused on building a comfortable place offering quality products and giving people a good start to their day, he said. Soon, this small coffee shop, with its orange and yellow walls and chalkboard menu, became a community hotspot.
Diego Lasso, the “mayor” of Simon’s Coffee Shop, talks with Prapti Sekhon in Dec. 2025. The two friends say it will be a huge loss to the community if development means the shop has to close.
Sekhon said the community she found at Simon’s changed her life. When she moved to Cambridge, she said, she was isolated and trapped in an abusive relationship. She credits the people at Simon’s for helping her get through it. “I couldn’t have survived … and this Simon’s community came together to literally help me,” she said, teary-eyed.
Sekhon said people from Simon’s invited her to meals when she could not afford them, walked her dog when she was going through a spinal injury, took her to appointments, and offered an ear when she needed to talk. The group of around 15 people was the first set of friends she made after she moved to Cambridge during the 2020 pandemic.
“It was life-changing for me. And here I am, like, a year-and-a-half later, and my life has changed,” she said. When her old apartment lease ended, she found a place as close as possible to Simon’s, and today she lives only three minutes away. She said it was “heartbreaking” to hear the news of the possible temporary closure and displacement.
Sekhon first met Lasso after she brought her golden retriever, Jelly, to the coffee shop in 2023, and he asked to pet the dog. She said Lasso, who has been coming to the coffee shop since 2012, is the group’s stable presence.
“If Simon’s is open, Diego is there,” Lasso said, referring to himself. “There is something about the friendliness of the staff, the friendliness of Simon himself, the way the place is designed that leads [people] to want to come here and to return.”
When he is not reading the newspaper, Lasso said, he talks with other regulars.
“We come to have conversations about other things, about the little things,” he said.
“It’s inevitable that I have to relocate or close, for the time being, until this project is done. I don’t know what’s gonna happen, so I don’t want to speculate [about] anything yet. — Simon Yu, owner, Simon’s Coffee Shop.
Yu said his favorite part of having owned the space for 23 years is seeing previous regulars, who graduated from college or left Cambridge, come back years later to reminisce.
“It’s so joyful to watch people come back five years later with kids, with [their] couples … to remember,” he said. “I’m glad to offer the space and ambience for those people who come to enjoy their time, meet new people and share new ideas.”
He said he was informed of the new development in October, and plans to stay open until the building is demolished. Yu said he was offered a spot in the new development, but he is considering relocating because of the prospect of keeping his shop closed for nearly two years.
“It’s inevitable that I have to relocate or close, for the time being, until this project is done,” he said. “I don’t know what’s gonna happen, so I don’t want to speculate [about] anything yet.”
Adam Siegel, a principal of Old North Development and Cambridge’s SGL Development, which acquired the property, declined to speak with Cambridge Day but wrote in an email: “We are diligently working with both Simon’s Coffee Shop and Keezer’s Classic Clothing on space planning for their return to the new project.”
“The Nieman Marcus of resale”
Keezer’s Classic Clothing, founded in 1895, moved into the basement of 1738 Massachusetts Ave. after Dick Robasson bought it in 2018, when he merged Keezer’s with his own company, Le Couturier House of Alterations. The establishment sells secondhand clothing predominantly for men and offers custom tailoring.
Keezer’s Classic Clothing, Dec. 2025. One customer called it the “Nieman Marcus of resale shops.”
Robasson said he does not plan to move until construction begins because moving will be costly. He hopes to find a spot in Harvard Square but assumes whatever he finds will be more expensive than what he pays now.
“We’re trying to move as late as possible,” he said.
Katiti Kironde has been going to Keezer’s since she was a Harvard undergraduate. Now retired, she has seen the store evolve under Robasson’s management, and said the store offers expert tailoring and quality high-end merchandise that is unmatched by other secondhand stores.
“Dick’s Keezer’s the Neiman Marcus of resale,” she said.
She said she was upset the store might have to move but stressed she was a “devotee” and would still go wherever the store moved to.
“It’s hard to find someone to fix stuff and fix them right,” Kironde said. “Wherever [Dick] goes, I will always follow him.”
This story is part of a partnership between Cambridge Day and the Boston University Department of Journalism.