From a sports team owner to billionaire philanthropists to content creators and radio personalities to business leaders, this year, 10 new visionaries in our communities made the grade. Read on to see who Northshore magazine inducted into our Top Influencers list in 2025.
CENTER COURT
Bill Chisholm
THE GEORGETOWN NATIVE and private equity mogul made history with his record-setting purchase of the Boston Celtics. When Bill Chisholm took ownership of the Boston Celtics over the summer for a cool $6.1 billion, he made his goal clear. “Coming in second is not the objective, and it’s not acceptable,” Chisholm is quoted as saying. “The ultimate yardstick is winning championships.” For anyone who grew up in this region, his passion makes sense.
“I became a rabid fan during the Bird, McHale, Parish era. That was my team,” Chisholm told The Associated Press. “How can you be a teenager in Massachusetts, or New England, with that group and not end up being a lifelong Celtics fan?” Now, Chisholm leads a group that has majority ownership control of the Celtics and will have full control by 2028, bringing the total potential value to $7.3 billion. Chisholm is now cofounder, managing partner, and chief investment officer at the California-based private equity firm, STG Partners. But his North Shore, New England, and athletic roots run deep.
Before he was paying record a price for an American professional sports franchise, Chisholm was a kid in Georgetown who loved soccer and whose dad helped establish the Georgetown High School soccer program. He was also a star athlete at Brooks School in Andover, where his mother worked for decades, and even received the Boston Globe’s All-Scholastic award for his senior soccer season, in addition to playing basketball and lacrosse.
Chisholm continued playing soccer at Dartmouth College in New Hampshire before going on to earn his MBA from The Wharton School in Philadelphia. Now that lifelong love of sports and the Celtics—Chisholm is said to have encyclopedic knowledge of the team—has hit the ultimate crescendo for that kid from Georgetown, who’ll have all eyes on him and his team when they take the court for the start of the 2025- 2026 season.
THE MULTITASKER
Jennifer Buras
When Jennifer Buras’s nowadult sons were in school, she’d see them off every day with the advice to “shine your light into the world.” It’s a piece of guidance she also tries to follow both in her own career as a professional advisor for senior executives at Essex Partners and in her community work. Buras has had four different careers—five when you count motherhood, she notes—working in accountancy, communications, and recruiting before ending up in her current role. Her dedication to supporting nonprofits, however, has remained unchanged throughout the years.
“I am a big believer that if you have been fortunate to have opportunities in life, you have an obligation to try to help lift others up,” says the longtime Swampscott resident. “Incrementally, one good act at a time makes the community better.” Buras has brought this philosophy to her support for a range of community organizations including Northeast Arc, local nonprofit news site Swampscott Tides, and her sons’ alma mater St. John’s Prep in Danvers.
Central to Buras’s community work, however, has been her involvement with the YMCA. She first became involved more than 20 years ago, helping with efforts to raise money for the construction of the Lynch/van Otterloo Y in Marblehead. She served on the corporate board of the YMCA of the North Shore—the 21st largest Y system in the country—for many years, including a five-year stint as president that ended in 2024.
The Y has had a special place in Buras’s heart ever since she was a child doing gymnastics at the Salem location. She admires the organization’s commitment to serving people of all ages and income levels equally, and its mission to provide affordable housing through the facilities it operates in Beverly, Gloucester, Haverhill, and Ipswich. “The Y has been a huge part of my life,” she says. “There’s no organization, in my opinion, that touches so many aspects of our community.
CLASSIC CHEF
Jason Carron
THE CHEF/OWNER BEHIND Post 1917 Steakhouse is bringing a modern take to the classic steakhouse. Back in the day, no dining experience was more luxurious than that of the steakhouse, with its high-end cuts of meat and dark, moody décor, replete with cherry wood and leather seats. Now, chef Jason Carron is reimagining what a steakhouse can be with a fresh take on that classic experience as owner and head chef of Post 1917 Steakhouse.
“We took the inner workings—the steaks, the sides—and we modernized it with what we did with the décor,” he says. “You walk in at each location, and you’re blown away by the lights, by the simplicity, and the beauty of the woodwork, the wallpaper—we’ve taken that classic and turned it into what I think is a play on modern steakhouse style.” Post 1917 Steakhouse is a true fine dining experience, with delicious, farmto-table food and polished service, as well as a menu that’s mostly gluten free. It’s no wonder, then, that Post 1917 has had such an incredible trajectory in the short time that it’s been on the dining scene.
Carron opened the first location in Reading in 2024 and quickly followed that up with a second location in Lexington over the summer. The steakhouse’s third spot is slated to open in Somerville in the spring of 2026, and Carron hasn’t ruled out others. Carron worked in restaurants for years, not only in kitchens in California, Cape Cod, and Capri, Italy, but as owner of Avery Restaurant Consulting, which helped hundreds of struggling restaurants right the ship.
It’s Carron’s combination of business acumen, culinary skills, and hospitality that has allowed the first restaurant venture of his own to be such a smashing success. And the food itself? It has brought Carron to tears. “I remember the first time we sat down to eat and I ate our food at POST,” he says. “I cried. I was like, this is so good.”
THE INITIATOR
Nancy Batista Caswell
ANYONE WHO HAS been fortunate enough to dine at Brine in Newburyport knows that Nancy Batista Caswell can turn out a great meal. But the acclaimed restaurateur’s work goes well beyond composed oysters and roasted duck breast. “I was mentored into this idea that in order to be successful, you really need to participate within the community and have a sense of community involvement,” Caswell says.
And she has taken that lesson very much to heart throughout her career, making it her mission to boost the people and businesses around her. She started off when she first came to Newburyport more than 15 years ago by supporting local nonprofits dedicated to women, the arts, and food security. As time went on, she joined the boards of some of these groups and earned a reputation as what she calls an “initiator”—someone who turns ideas into action.
Today, she brings that strength to several roles. She is president of the Greater Newburyport Chamber of Commerce and Industry, where she sees her role as establishing the region as a lifestyle destination, making it appealing in a way that strengthens all area businesses. She is also the co-organizer of the EmpowerHER Summit, an annual event that convenes women from different fields to inspire and empower one another; last year’s event drew more than 200 people. Caswell is also involved in shaping the state and federal policies that affect her community.
Last year, she was a leader in the fight for state ballot question 5, which would have required tipped workers to receive standard minimum wage. She has also traveled to Washington, D.C., to advocate for policies that give immigrants a pathway to citizenship, an issue that is near to her heart as the daughter of two Portuguese immigrants. “Immigrants are within our communities. They are our neighbors,” she says. “But their voices aren’t loud enough, so I make it a point to speak on their behalf and advocate for them.”
A RARE GEM
Steven Leed
THE CEO OF Royal Jewelers does more than sell watches and jewelry. He also builds relationships and makes memories. Steven Leed’s father always said, “The people who shop at Royal Jewelers are more valuable than the jewelry we offer.” “I grew up respecting that phrase,” Leed says. “The client experience has always been and always will be, the major focus of what we do.” Now, he continues to live by that ethos as CEO of the Andover-based luxury jeweler. Leed bought out his sister and former business partner and now is sole CEO of the business, which Leed’s father founded in Lawrence in 1948 after serving in WWII.
Today, Royal Jewelers’ 5,000-squarefoot boutique showroom in Andover is a place where customers from around the world come to shop for jewelry and watches from the best and most fashionforward designers and brands, so it goes without saying that each piece is special. But selling pretty jewelry is only one part of the customer experience. That’s because Leed and the shop’s sales advisors, watchmakers, and jewelers understand that a piece of jewelry is often more than a bauble or fashion accessory. It also often carries deeper meaning and importance, something to celebrate and commemorate a significant milestone or a special time in someone’s life. “This is going to be a sentimental piece of jewelry or wristwatch that forever they’re going to look at and remember the significance of what it meant to them,” Leed says.
It’s because of that Leed says the relationships they develop with clients are so important and meaningful, with sometimes fourth and fifth generations of families continuing to turn to Royal Jewelers time and time again. “I have spent the last 50 years at Royal refining the client experience and am extremely proud to be at the helm as CEO,” Leed says. “It is a privilege to have guided Royal from a local jeweler to a jeweler of international recognition.”
THE PHILANTHROPISTS
Bill and Joyce Cummings
At a time when many of the richest Americans are trying to accumulate yet more wealth, real estate magnate Bill Cummings and his wife, Joyce, are working on plans to do just the opposite: They’re trying to give away everything they can. The couple’s grantmaking organization, the Cummings Foundation, has given away $600 million since its inception in 1986, and has no plans to slow down. It’s a process that is “great fun,” Bill Cummings told Northshore in 2022. Each year, the foundation commits $30 million in multiyear awards to greater Boston charities and nonprofits. The latest round of grants, announced in July, included $500,000 to Lawrence nonprofit Uncommon Threads, which provides clothes to lowincome women; $300,000 to Newburyport food insecurity program Nourishing the North Shore; $210,000 to Gregg House, a Lynn education and childcare organization; and millions more.
The Cummings Foundation began in the 1980s, formed to give back to the communities in which Cummings Properties built their commercial developments. In 2011, the Cummingses became the first Massachusetts residents to sign the Giving Pledge, an initiative asking billionaires to publicly commit to giving away most of their wealth. The Cummingses earned their status as billionaires in the commercial real estate sector, starting with a single office building in Woburn in the 1970s. Today, Cummings Properties manages more than 11 million square feet of space in greater Boston. And the properties that grew the family’s wealth are also the engine of its ongoing charitable work.
The foundation owns most of the properties in the Cummingses’s portfolio and uses the revenue to fund its work. The commercial company manages them pro bono for the foundation. Bill Cummings, now 88, expects the foundation to be around, fulfilling his mission, long after he is gone. But for now, he enjoys seeing what his money can do for local communities. “Rather than leaving it around for somebody else who gets to give all the money away, we thought, ‘Why not start now, to be a part of it?’” says Cummings.
THE CONTENT CREATOR
Alaina Pinto
THE TRAVEL CONTENT creator shares her love of New England and be – yond with her social media followers. Alaina Pinto might not have been born in Massachusetts, but the writer and con – tent creator’s love for her adopted home state is undeniable. As soon as the Mid – west transplant arrived in Vermont in 2014 for a job with a local news station, she felt at home. “I fell in love with it so, so hard and so fast,” she says. “I knew that this was my place.” Traveling throughout Vermont with that job sparked a passion for exploring New England that hasn’t waned in over a decade.
“I love the nature. I love the mountains. I love the beaches. I love the old architecture and the cute neighborhoods,” she said. “I never want to leave.” She couldn’t even bring herself to leave when she was fired from a news anchor job in Boston in 2020 for mistakenly violating her contract. The infraction? Appearing in a brief cameo in the Adam Sandler film, Hubie Halloween, which is set in Salem and was filmed on the North Shore.
Instead of taking a job at another news station in New York or North Carolina, Pinto decided to strike out on her own. “I just couldn’t see myself leaving New England,” she says. “I decided, why don’t I just share my own travel stories on my platform?” That’s exactly what she’s done on – line and across social media, where she’s brought her followers along on adventures like kayaking with seals in Rock – port, making custom Converse sneakers in Boston, biking to East Beach on Chappaquiddick Island, and hiking Mount Hight in the White Mountains. She’s also in the process of creating a podcast and expanding her travel content through – out New England and beyond. “I want other people to enjoy this region as much as possible,” she says. “This is the most magical place in the United States.”
THE COMMUNICATOR
Kim Carrigan
KIM CARRIGAN HAS been curious ever since she was a child growing up in Missouri. She’s always been driven to ask questions and then talk to people to learn the answers, she says. “That’s been in my blood since I was a kid,” says Carrigan, a Swampscott resident. That motivation—to ask and learn and share—led Carrigan to a successful career in news. Her name and face are familiar throughout the region from her time as a TV news anchor for WHDH, WBZ, and Fox. Today, she cohosts a weekly business radio show on WRKO and has a popular lifestyle podcast, Carrigan & Company.
Each week of the podcast, a cohost—the “company” of the title—joins the show, and Carrigan and her guest explore topics from the fun to the formidable. Recent episodes have covered the Boston Film Festival, Alzheimer’s Disease, and books by local authors. Carrigan’s favorite episodes are the ones that give her a chance to talk with people about something more than what they’re known for, such as when she spoke with fellow news personality Mike Lynch about his experience having a stroke. “I love to give people a platform to tell parts of their story that aren’t always heard,” Carrigan says.
When she’s not recording, she is also deeply involved in charitable work, acting as host for events like a fundraising fashion show in support of disability advocacy group Northeast Arc and a day of action at Encore Boston Harbor at which volunteers packed nearly 600,000 meals for area organizations. What’s up next? Well, Carrigan can’t say quite yet, but she’s excited to share it with audiences when the time comes. Current fans can rest assured, however: Her radio show and podcast will also be continuing even as she dives into some – thing new. “I’ve got a few things on the horizon,” she says. “I am always looking for new adventures and new ways that I can use or hone my skills.”
THE ITALIAN HOST
Paul LaRosa
LAROSA HOSPITALITY GROUP has expanded beyond Andover with the new LaRosa’s Italian Restaurant in Newburyport. For years, Paul LaRosa’s restaurants have been staples of the Andover food scene, starting with LaRosa’s Café, a sandwich shop that opened in 2009 and quickly became part of the community. “We really wanted to get to know people’s names and really entrench ourselves,” says LaRosa, who is owner/partner of LaRosa Hospitality Group. They did exactly that, and thanks to the success of that first venture, LaRosa went on to open three more restaurant concepts in Andover—La Fina Steakhouse, Privé Lounge, and The Autograph American Tavern—each with its own unique atmosphere and vibe.
Now, LaRosa Hospitality Group has expanded its reach outside of Andover for the first time with LaRosa’s Italian Restaurant, which opened in May 2025 in Newburyport, bringing its delicious Italian cuisine to Market Square. Already, it’s a smashing success, with a prime location downtown, patio seating, standout cocktails, and classic menu items, like the Bolognese with braised lamb that LaRosa calls “outrageous.” “It was a home run for us,” LaRosa says. “It’s been a huge, huge success. I think the community really loves it.”
LaRosa says he’s had such an incredible experience in Andover being part of the community, and he’s eager to have the same experience in Newburyport. But no matter where his restaurants are located or what they’re serving, LaRosa’s passion and focus always comes back to the same thing: Hospitality and giving customers a great experience. He hopes that after a long, hard day, people can come to his restaurants, leave the world behind, and feel like they’re being treated “like a king or a queen.” In fact, he says, “the food is almost the easy part.” “It’s the other things that matter the most—that’s what hospitality really is,” he says. “It starts with the front door. The minute you walk though, you’re greeted with a smile.”
THE CAREGIVER
Roxanne Ruppel
WHEN ROXANNE RUPPEL was a child, watching her father suffer from serious cardiac issues, she was inspired by his caregiving team, by the way they prolonged his life and improved his wellbeing along the way. These observations planted the seeds of her future career in the health care field. “I knew early on in life that I wanted to take care of patients,” Ruppel says. “To be honest, I never thought I’d do anything else.” Ruppel started off as a physical therapist, working daily with patients. About a decade into her career, however, she was offered a chance to take on a management role. She worked her way up through positions in operations, strategy, and planning until she was named president and chief operating officer of Salem Hospital in 2023.
Along the way she discovered that working on the administrative side allowed her to support patients and providers alike in ways she found im – mensely gratifying. In fact, this focus on giving doctors and practitioners what they need to help their patients has been a theme throughout her management career. “My role is really to ensure they have all they need to deliver exceptional care every day,” she says. Since stepping into her current position Ruppel has worked to balance the hospital’s ongoing growth with the need to maintain the highest quality of care. Under her leadership, the hospital has begun expanding its robotic surgery program across specialties and opened up more access to both in-patient and out-patient psychiatry services.
And the hospital’s commitment to excellence is attracting attention: Earlier this year, Salem Hospital was named one of the best hospitals in Massachusetts by U.S. News & World Report. Even as she concentrates on the big picture, however, Ruppel’s favorite moments happen when she is doing rounds with providers or meeting with frontline staff—anything that brings her closer to the patients she started her career to care for. “The closer I am to the patient interface, the more fulfilling the job is,” she says.
Meet some of these power players at Northshore magazine’s Top Influencers event October 22, at The Cut in Gloucester. Click here for tickets.