Early work with Anti-Defamation League helped shape career of Boston attorney
By Brian Cox
When he was a college student, Robert “Bobby” Rudolph spent several summers working at one of the largest car dealerships in New England. He closed more sales than many of the full-time career salespeople, and it’s where he learned a lesson he’s carried with him into the practice of law: A quick response is the key to top quality customer service.
“I didn’t want to be a car salesman, but the mentality of having to be responsive to customers has stuck with me,” he says. “One of the things that I have always tried to do, and pride myself on, is being responsive because a lot of our clients’ issues don’t arise at 1 p.m. on a Tuesday.”
So, when a client is in need of counseling, even at inconvenient hours, Rudolph makes it a point to be at hand.
“Even though I know it may not be the biggest issue in the world, or that it’s something we can easily resolve through the court process, or in response to a motion, for the client it is the biggest issue in the world and they’re not sleeping because of it,” he says. “They’re thinking about it all the time and it’s my job to take that burden off of them and to get them a good result.”
The lesson was reinforced by watching how his father, Jim Rudolph, a founding partner of Rudolph Friedmann LLP, engaged with clients and fully dedicated himself to the legal profession. When Boston Magazine named Jim Rudolph the Best Lawyer in Boston in 1998, Bobby Rudolph was 12 and remembers understanding how big an accomplishment the honor was for his father.
“I remember eating dinner and my dad coming home in his suit every night and then going into his home office and working,” recalls Rudolph. “I think I saw from him how proud he was of what he did, how hard he worked at it and the results that he got from it, whether it was recognition in the community or winning a big case.”
His father’s work made an impression on young Rudolph, who even from an early age showed a lawyer’s inclination to express his opinion, whether it was a popular position or not. In high school at The Governor’s Academy, he was awarded the Headmaster’s Cup his senior year, in part for his leadership in responding to a series of hateful online posts by a few academy students. Through his work with the Anti-Defamation League’s (ADL) Peer Training Program at the school, Rudolph helped organize a campus-wide convocation and brought in national speakers to address the incident.
“I think it really brought a sense of community to campus, and everyone rallied around standing up against hate,” says Rudolph.
Attorney Bobby Rudolph (right) with his father, Jim Rudolph, and Jon Friedmann celebrate the law firm’s 20th anniversary.
Rudolph identifies attending The Governor’s Academy, a college-preparatory boarding school established in 1763 that his father also attended, as a turning point in his life. Born and raised in Swampscott, Mass., a small town in the North Shore about 15 miles north of Boston, Rudolph says the academy quickly forced him out of his comfort zone.
“It’s easy growing up in a small town to only socialize with the same people,” he says, “and you get comfortable in your community.”
But at The Governor’s Academy he was encouraged to branch out and to take on a range of extracurricular and leadership roles. The school’s student body was diverse, with students from different countries around the world.
“I think it was there where I saw how being involved in the community could make an impact,” says Rudolph.
He became active with the ADL’s Peer Training Program, which works to motivate students to take action against prejudice and bigotry in their schools and communities. Rudolph’s father had been involved with the ADL for decades, so Rudolph had been exposed to the organization’s mission while growing up. But becoming a youth trainer in the Peer Training Program marked the beginning of Rudolph’s own personal journey with the ADL, where he remains very active, serving on the ADL’s New England Regional Board and several of its sub-committees.
In 2020, he received the ADL’s Daniel R. Ginsburg National Leadership Award in recognition of his work in the fight against antisemitism, racism, and all forms of hate.
After graduating from The Governor’s Academy, Rudolph attended Colby College in Waterville, Maine, where he studied economics and dedicated a part of his time to skiing at Sugarloaf Mountain. He spent the fall semester of his freshman year in Salamanca, Spain, where the school has a language acquisition program. Rudolph lived with a host family that didn’t speak English. His junior year, he studied for a semester in Melbourne, Australia.
“I had a drive to experience something outside of what I was used to,” says Rudolph. “I was a kid who grew up in a small town and loved steak tips and potatoes – I came back home and I was eating paella and sushi; having tried kangaroo and crocodile. They are experiences I’ll always cherish.”
Following the encouragement of his father, Rudolph wasted no time after earning his undergraduate degree before pursuing a juris doctorate. His father had convinced him that law school would be a good background for anything he wanted to pursue in life. His older brother had also gone to law school, though he went on to work for their grandfather’s real estate company rather than practice law.
“I had the perspective that it’s much easier to be a lawyer and decide to do something else later on than to graduate law school, do something else, and then be a lawyer,” says Rudolph, who thought at the time that he would follow his brother into business.
He had an interest in real estate and thought law would be a good background for handling contracts and transactions.
His plans shifted slightly after his first year of law school, when he won awards for oral advocacy and legal writing, and suddenly thought, “maybe I’ll see this thing through.”
During his 1L summer, he interned with the district attorney’s office and gained experience in the courtroom and with how attorneys interact with judges. The next year he was a summer associate at a mid-size firm where he gained more litigation experience, cementing his desire to become a litigator.
Through law school, he didn’t live far from the Boston office of his father’s firm and on the weekends, instead of going to the library, he would often study in one of the firm’s conference rooms. Jon Friedmann, a named partner, and another partner, Jim Singer, were usually working on Saturdays and the two encouraged Rudolph to join the firm. The men would become important mentors to Rudolph after he came on as an associate in 2012.
Bobby and his wife, Amanda, who is also an attorney, were married in October 2022.
“It was almost like I was working with them before I even joined the firm,” says Rudolph with a laugh. “So, when I joined the firm right out of law school, I had already become acquainted with the partners I was working for and was able to jump right into things.”
From the start, Rudolph set out to prove he wasn’t at the firm just because he was the managing partner’s son. He worked closely with Friedmann and Singer, learning to take depositions, argue motions, and conduct trials. He quickly became involved in mediations, arbitrations, and second-chairing trials.
He and his father had their offices on different floors and intentionally kept their professional and personal relationships separate.
Rudolph remembers working as a runner at the firm one summer when he was in high school, getting lunches, delivering mail, and couriering documents to the courthouse. At midday on his first day, he took his lunch into his dad’s office to eat with him. His father made it clear he shouldn’t expect to be able to have lunch together every day.
A lifelong Celtics fan, Bobby attended the 2024 NBA Finals with Amanda.
“‘You work here now,' he told me,” says Rudolph. “‘You’ve got to develop into your own and be an employee and be part of the team.’ I think that set the tone going forward.”
When he became an associate, if Rudolph called his dad at night, his father would first ask if he was calling as someone who worked at Rudolph Friedmann or as his son.
“Because if it’s something about Rudolph Friedmann, call me in the morning,” his father would say.
“We tried to be intentional about maintaining some separation and I think it worked well,” says Rudolph. “I’m very lucky to have the opportunity to work with my dad. He’s a great attorney, a great mentor, and he’s been excellent to learn from.”
Rudolph has also drawn on lessons learned from his mother and maternal grandfather. His mother’s unwavering support provided him with a firm foundation, and his grandfather was a significant, influential figure in his life.
“He was the definition of a gentleman,” says Rudolph of his grandfather, who built a successful mortgage and real estate company. “He was the most patient and caring man, and for him, it was all about family and treating people correctly. I think I learned from him what being a good person is and how important family is.”
Rudolph now has a family of his own. He and his wife, Amanda, were married in October 2022 and have a daughter, Ella. Amanda is also an attorney; she represents mutual fund boards for an international law firm.
“It’s nice in the sense that we understand the responsibilities of the profession,” says Rudolph about being married to another lawyer. “We understand that sometimes you have to work late or take a call in the middle of dinner. But it’s kind of equivalent to a dentist and a heart surgeon being married. We don’t speak the same language.”
During his first few years of practicing, Rudolph concentrated on building relationships with clients and other attorneys, determined to demonstrate that he was capable of handling their matters and getting results.
His practice now focuses primarily on issues related to business, employment, real estate, and construction. He also litigates highly contentious shareholder disputes between owners of closely held businesses. Working with property owners, developers, contractors, and material suppliers, he handles a diverse range of real estate and construction related issues, including disagreements with abutters and construction disputes.
He has worked with many of his father’s clients over the last 12 years and has built relationships with them. With some, he has worked with their children who are the next generation taking over the business, which Rudolph says is a special opportunity to carry on the relationships far into the future.
Now an equity partner in the firm, Rudolph is involved in day-to-day decision making. He is committed to being accessible to younger attorneys and affording them opportunities in the same manner Friedmann and Singer helped him develop as a lawyer.
“It’s a lot about team building and making sure people feel valued and appreciated and helping them be the best attorneys that they can be,” he says. “I’m trying to shape the future of the firm so that it can continue to be successful for many years to come, and I think that starts with having a good team and helping bring the best out in them.”
