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.
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.
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.
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I like Simon’s and Keezer’s but what is truly heartbreaking is people having to spend half their income on rent or face long commutes because they can’t afford to live near their jobs. Heartbreaking is also having our city streets clogged with traffic because people have to drive instead of live here. Cambridge creates jobs. It also needs to create housing.
Let’s get some perspective on “heartbreaking”.
And BTW, more people living here mean more customers for local businesses.
I enjoy Simon’s and hope/expect that they will not be permanently lost.
At the same time, the city does need housing, both market rate and affordable. In the City’s annual resident survey, “Market rate housing that is affordable” is consistently rated as the #1 most important issue by Cambridge residents, and “Affordable housing (that is, subsidized or income-restricted for low, moderate, and middle
income families)” isn’t too far behind:
https://www.cambridgema.gov/-/media/Files/citymanagersoffice/residentsurvey/2025residentsurveyresultsandbenchmarks.pdf
Cambridge is far behind on its Envision housing production goals, both the number of total units, as well as the number of affordable units:
https://www.cambridgema.gov/envision/Housing
Councillors that don’t live in the neighborhoods and aren’t going to be directly affected by all the construction and the destruction of the neighborhoods should NOT be the ones making the decisions in Cambridge on everything that has been passed. Story after Story I’ve seen is about loss so a bunch of new strangers can come in who have no real connection here. Who Benefits? The Developers and the Money Men and likely councillors who have undisclosed connections to them. Expand the tax base is all its about, just like they did with all the now empty Lab Space etc. We even had it pushed thru by a now departed councillor who suddenly is living off somewhere on a Farm according to the newsletters he sends out far from the City.
Rather than blocking housing during a housing crisis, perhaps Simon’s and Keezer’s patrons should do something more productive like starting a GoFundMe to help with temporary relocation costs.
If councilors weren’t allowed to make decisions on neighborhoods they don’t live in, city government would cease to function.
Who benefits? People who need affordable housing.
@Reader Where in the article does it say ANYTHING about Simon’s and Keezer’s patron trying to block housing?
@Frank, barely. There are much better ways to build out a stock of affordable housing units than to destroy the cityscape with sterile architecture while displacing beloved cafes and other stores that are seen as critical to local residents.
Cambridge will not be made “affordable”. But, affordable housing can be built, while also attending to local needs and compelling design. 1740 Mass Ave isn’t that.
It’s a direct handout to developers, on the order of $5MM-$6MM per year in revenue. 70+ units most of them sub-500 square feet, renting for $3200+ per month.
The local community does not want this.
The acquisition of buildings and/or land by the city for the express purpose of providing affordable housing to low-income residents is the right approach.
@adiletta The local community does want this. Voters made that clear in the last election by supporting candidates who favor housing reform and rejecting those who want to roll it back. Surveys of Cambridge residents consistently show that housing costs are the top concern.
And yes, building more housing does help bring costs down. Cities that increased density through zoning reform have seen rents and prices rise more slowly than comparable cities that did not.
Source:
https://www.tandfonline.com/doi/full/10.1080/10511482.2024.2418044
Housing is also, quite simply, essential. People need places to live. That matters more than preserving a single retail shop. For those calling Keezers “beloved,” when was the last time you were actually there?
Me? I am a semi-regular at Simons and shop at Keezers. But I am less concerned about myself and more concerned about the greater good and helping vulnerable members of our community.
New housing in Cambridge needs to do two things at once: add income‑restricted units and add overall supply so rents stop outpacing wages; 1740 Mass Ave does both.
Calling it “sterile” or a “handout” is about taste and framing, not policy. Inclusionary projects use private capital and some market‑rate rent to permanently subsidize on‑site affordable homes, which the city cannot replicate at scale through acquisition alone given land costs. Developments like 1740 Mass Ave are the only viable way forward to address the housing crisis.
“The community” is not just existing nearby homeowners and café regulars; it also includes low‑income residents and people on long waitlists for affordable housing. Those community members wants this. They benefit directly when more mixed‑income housing is allowed on transit‑rich corridors like Mass Ave.
@AvgJoe – No, calling it sterile and a handout are statements of fact. People don’t like contemporary/modern architecture. We have a choice in how we build the city, and continued pursuit of these buildings makes the city weaker, not stronger, over time.
https://www.currentaffairs.org/news/2017/10/why-you-hate-contemporary-architecture
Once again, we can build affordable housing for low income residents without pursuing current policies.
@Frank, you will do nothing to mitigate rising housing costs. You can continue to drop into every message board on the Day and post the same things over and over, that does not make it true.
There are a rising group of folks, myself included, that will start pushing back on this. Cambridge will not be “affordable”. You will not roll back rising rental costs.
That said, we can build affordable units, which should be done through land and building acquisition, and commercial conversions.
Truth rests on evidence. The evidence clearly shows that building more housing lowers costs.
There is no evidence that it won’t work here. There can’t be, because it hasn’t been tried. Claiming otherwise is unsubstantiated opinion that runs counter to the data.
Disliking modern architecture is a matter of taste. I happen to like it. And it’s odd to complain about architecture when the building being replaced is nondescript and unattractive.
If someone can’t support affordable housing near public transit, especially when it replaces an unattractive building, it’s hard to see how they can claim to support affordable housing at all.
The building there now is sterile. If it is going to stay sterile, it should at least include the housing Cambridge desperately needs.
The rising group is Cambridge residents who consistently say housing is their top concern. Recent elections show strong support for candidates who back more housing and zoning reform.
What truly weakens cities is a housing crisis that pushes out everyone but the wealthy.
The only real “handout” here has been exclusionary zoning, which helped inflate existing homeowners’ property values while limiting who could afford to live in the city.
What I keep hearing is “it won’t work here.” Repeating that claim does not make it true.
There is no evidence that Cambridge is exempt from basic housing economics. Cities that have added substantial amounts of new housing have generally seen slower price growth than comparable cities that did not.
Proposing plans with no realistic path to implementation is effectively another way of saying no. The city lacks the fiscal capacity to build all the housing it needs on its own.
Even if new development does not dramatically lower average rents citywide, it will still create thousands of permanently affordable homes for families that need them. That is a core housing goal and a clear win.
1740 Mass Ave is an ordinary building. Does preserving that matter more than new housing with affordable units for families who would otherwise be priced out?
The photos accompanying this article stand in eloquent testament against a development plan that destroys existing mom and pop businesses, replacing those vital urban neighborhood components with first-floor commercial space that only deep-pocketed national chains can afford.
Then there’s the “70+ units most of them sub-500 square feet, renting for $3200+ per month”. Sounds like a glorified dormitory for singles and couples who can afford extortionate rents for not much space. It’s hard to imagine many tenants choosing to settle in for the long term, certainly not if they plan to have a family.
There has got to be a way to build genuinely affordable urban housing designed to support long term occupancy and preserve the local businesses that provide essential, affordable and unique local services, including community meeting space. These qualities are surely essential to make life in an urban community joyful and meaningful.