L to R: Moderator and CD President Chris Weiss, Dawson and Tami Rutter of Commonwealth Worldwide, and Brett Barenholtz of Above All/Maine Limousine
Here at Chauffeur Driven, one of the most inspiring things we’ve learned since our first issue is that everyone has a story. Whether it’s the operator that started with a single stretch, the second-gen owner that’s taken over the family business, or even the once part-time hustler that now has an impressive fleet, the fact remains that the diverse backgrounds of the operators we’ve profiled have informed and inspired countless industry professionals.
So, when it came time to conceive new programming for our annual Vegas event, CD President Chris Weiss was energized by the tales often printed in our pages, with a twist. He was looking to get in-depth with an industry titan who was not only willing to share insight and industry history with candor and humor in a casual, laid-back setting, but also open to discussing their personal side—unfiltered.
Thus, CD Presents: Legends & Origin Stories was born. Introduced at the 2026 CD/NLA Show in Las Vegas this past March, this one-on-one live interview segment, open to all attendees, delivered on its promise, with its focus on industry icon Dawson Rutter, the CEO and founder of Commonwealth Worldwide, one of the most respected companies in our industry.
Dawson and Tami Rutter shared hilarious personal stories Naturally, Rutter was an ideal choice for the debut of the Legends & Origin Stories, as his history within the luxury ground transportation industry runs deep, and best of all, he’s an exceptional storyteller, loaded with anecdotes and life lessons. Together on stage, Weiss and Rutter discussed the operator’s past—touching on both the sordid and triumphant—over a bottle of Italian wine and in the company of a few hundred fellow industry professionals. No punches were pulled, whether it was a hilarious story about his beloved pooch Winston, friendly (and not-so-friendly) fire among competitors, or sweet and vulnerable moments with the people who meant so much to him. Emotions from every angle overflowed.
Of course, it was the gritty stories from the ’70s as a Boston cabbie that kicked things off and were often the funniest.
“I started driving a cab in 1973, and was on and off as a cabby for eight years. It was awesome. It was so much fun,” Rutter revealed as he turned back through the (often literally) hazy mists of time. Back then, safety culture and regulatory compliance were in their infancy—almost like the wild west of transportation, baring little resemblance to today’s regulatory environment. The unpredictability of the era was only matched by the unpredictability of the job, although the “survivor” stories are bonkers.
In more epic stories of his days as a wayward cabby, one saw him get deserved justice after a local ne’er-do-well beat him for a 60-cent fare, while another story involved the horror of a late-night hold up. Even local celebrities slid into the back of his cab, which were often tales so salacious that they are not safe for work—a mix of dangerous but genuinely funny.
While Rutter recalled a flash of people who made his early days interesting, he more memorably remembered those who made it worthwhile.
Early on in his career, Rutter found himself behind the wheel of a yellow cab, driving for Boston Cab, a company owned by the father and uncle of another icon, Brett Barenholtz of Above All/Maine Limousine. Before long, Barenholtz joined the pair on stage to regale the captive audience about their lifelong friendship as friendly competitors.
“I met Brett when he was 12 years old. I was 22, and I was working for the company, and Brett would come and hang around the garage with his cousin, and they would, you know, do stuff around the garage. So, I’ve known Brett now for 52 years, to be exact,” said Rutter.
Rutter isn’t just a colleague—he was a steady presence as Barenholtz grew up. Likewise, Barenholtz appreciated Rutter right from the start, and a close relationship continues to this day. Barenholtz looks fondly upon the kind of mentor who doesn’t soften his words, who will tell you bluntly when you’re wrong, and somehow make it feel like a favor instead of an insult.
“In those days, I would just check the oils, the transmission fluid, and the power steering fluid,” Barenholtz shared about working for his father’s business. “A hundred cabs would come in, and I checked them all. Dawson would come in, and I thought he was very generous because he would tip me. A buck was like a big deal then.”
As the ’70s rolled into the opulent ’80s, Rutter entered the limousine side as a chauffeur. Taken by the industry, he eventually purchased a brand-new Cadillac formal limousine with jump seats and broke out on his own.
“I cut my teeth on sightseeing. I started my limousine business by taking clients sightseeing all over the Boston area and the suburbs,” said Rutter.
And it was one of those tourists that set Commonwealth Limousine Service on its path, marking a major turning point for the bourgeoning company.
“The first week I was in business, I got a call from Boston Magazine to hire a car to take their new senior editor, John Brady, and his wife around the Boston area because he was coming from Cincinnati,” said Rutter.
Acting as chauffeur and tour guide, an excursion thorough Sleepy Hollow Cemetery in Concord just north of the city to see the famed resting sites of writers Alcott, Hawthorne, Thoreau, and Emerson left the Bradys speechless.
“And so I dropped them off back in town. Brady says, ‘Thank you very much, Dawson, that was great.’ And off they go. That was the first week that I started my limousine company,” said Rutter.
That trip would prove to be fortuitous, as it wasn’t the last ride Rutter would have with Brady. As his burgeoning limousine company was still finding its place in the market, Rutter continued to drive his taxi, until...
“I got a call from Brady. He said, ‘Dawson, what the hell are you doing driving a cab?’ And I said that business was slow, so I was driving a cab to make a living while the limo business was getting off the ground. I did the ride to Cambridge, and that was that.”
In a crazy twist of fate, Rutter owes Commonwealth’s start to a little classified ad he placed in Boston Magazine to help advertise his service—which had already been tested and approved by the magazine’s senior editor.
“I knew the staff in the classified ad department, and I get this call one day from them, and they said, ‘Congratulations, you’re Best of Boston 1983.’ It was unbelievable. I got flooded with work. I bought my third car, I bought my fourth car, I bought my fifth car. I stopped driving a cab, and I was off to the races.”
We all know the juggernaut that Commonwealth became and continues to be today, but the company wasn’t the only thing that grew. He also shared the tender moments of a blossoming friendship that led to marriage with his then national affiliate director, Tami Saccoccio (who also joined the stage). Saccoccio, now Rutter, walked into his company from a corporate world that had rules for everything, only to find herself in a place where nothing quite worked the way she expected it to. She cried for months, she joked, but she stayed. Over time, what started as friction turned into alignment, then friendship, then something deeper. Years later, they married and now split their time between Boston and Arizona.
We truly thank Rutter, Barenholtz, and Tami Rutter for the candid peak behind the curtain of their lives and careers. After all, if there’s an enduring theme in what we’re trying to accomplish with Legends & Origin Stories, it’s this: It’s not just about wild stories—fun as they are—it’s about the people who kept showing up for each other. Through cabs, companies, moments of generosity, and decades of reinvention, it’s the relationships that matter most.
We have a few names on our short list for the 2027 Vegas show, but one thing is for sure, we’ll keep it real. This is your official invitation to join us for another riveting Legends & Origin Stories next February, because you won’t want to miss a thing. [CD0526]
