When Robert Holloway Jr. tried out for the all-male Glee Club at
Amherst College in his freshman year in 1964, he applied as a first
tenor. The first tenor is usually the smallest group in a four-part
male chorus because of the demand to hit the highest notes. The
fallback was second tenor, which is easier to sing. Holloway vied
for the smaller group to increase his chances of getting
accepted. "He would have gotten picked, anyway," says Amherst
classmate and friend John Stifler, who now teaches economics at
UMass-Amherst. "I was interested that he had such a pragmatic
approach to the whole thing."
Holloway, the MBA's incoming president, seems to have a
pragmatic knack for hitting the right notes in many other
endeavors, but all who know him say he does so in a way that makes
other people shine. He is president and shareholder of MacLean,
Holloway, Doherty, Ardiff & Morse PC in Peabody, and a past
president of the Essex County Bar Association. He has served on the
Massachusetts Bar Association's Ethics Committee, and is an
emeritus member of the Board of Editors of Massachusetts
Lawyers Weekly, serving on that board since 1981. He is a
regular volunteer as a judge for moot court arguments at Harvard
Law School and at Boston University School of Law, where he
received his JD degree in 1973. And in his spare time, you may find
him at a piano or keyboard in any of several North Shore
restaurants or other venues, either solo or with band mates.
The smartest guy in the room
Meeting Holloway for the first time, the first thing that comes
across is that despite his small stature, he projects a presence --
a desirable trait in a trial lawyer -- but in a very low key way.
If you were expecting a master of the universe, as limned by author
Tom Wolfe in Bonfire of the Vanities, he's not your guy.
When he's asked about cases that particularly stand out, he avers,
"I've had the opportunity to work on a number of things that by all
rights, I shouldn't have had the opportunity to work on."
Early in his school career, he acquired the nickname "Stump," a
self-effacing moniker that became the title of his columns for the
college newspaper. The column title was On the Stump. "He
always seemed short, but he never seemed little," Stifler says.
Attorney Douglas Sheff of Sheff Law Offices, who will succeed
Holloway as MBA president, characterizes him as taking cases others
might deem as unwinnable, and turning disadvantages into
advantages. "He'll always say, 'after you,'" Sheff says.
Attorney Walter Costello of Walter A. Costello Jr. &
Associates has known Holloway for 30 years, both personally and
professionally. Both served as president of the Essex County Bar
Association. Costello typifies Holloway as very committed to the
ideals of the practice of law, possessing a high energy level, and
a willingness to step up to the plate to resolve difficult
Attorney Michael Tracy of Rudolph Friedmann has watched Holloway
work as a mediator. It's a mediator's job to convince the opposing
sides that they need to compromise. Through a gift of gab, Holloway
keeps discussions going rather than allowing them to fall into an
But he also knows when to pull back. Attorney Leonard Clarkin of
Clarkin & Phillips PC, who has seen him in court on at least 20
occasions, has this perspective: "I think the greatest skill of the
trial lawyer is to cross examine, to get the right result without
looking like a bully. 'Projects' is a great word. Bob is a great
cross examiner and always gets what he wants. When things get a
little edgy, he looks like the victim [of an unresponsive and
evasive witness' intransigence]. If you have an unresponsive
witness, call Holloway."
He adds, "He'll fight like hell in the courtroom, and when the
day adjourns he'll have a friendly conversation with the
What the people want
Those who know him say he has a knack for finding out how to do
what others need done, whether the work itself is attractive or
not. This trait has garnered him the informal position of class
Treasurer for Life at Amherst, "partly because people trust him and
partly because nobody wants to learn to do what you have to do to
be Treasurer," remarks Stifler.
Holloway likens the MBA presidency to being a team captain.
Active in many different team sports in high school and college, he
says the formative years stick with you, "particularly if you had a
good time," which he apparently did. His small physique did not
deter him from playing rugby in college, on a team that in senior
year Stifler says became one of the best collegiate rugby teams in
"Most team sports require that everybody be on the same page,"
Holloway says. Priority must be placed on what's best for the
group, not for a particular player. "I was never a star," he adds.
"I just felt lucky to be on a team."
He's all for giving others the credit, citing 200 to 250 MBA
members in leadership positions in various capacities in the
organization. "What separates some from the others is their ability
to implement and execute," he says, and then gets into a discussion
of how MBA officers come up through the ranks, the annual cycle of
officers actually plays out. The year is effectively only nine
months, from September 1 to June 30. In the remaining quarter, the
next round of officers are already starting to implement their
agendas. "If you want continuity," he says, "you need objectives
that will survive beyond any particular president."
Easing the pressure on courts
That's all the more important today. Holloway cites the decline
in involvement in trade associations across the country over the
last 10 years. "The legal profession has had its own issues
enhanced and exacerbated by an influx of new lawyers [for whom
there are] no jobs," he says. Then there's the issue of court
funding, over which the MBA has been "a loud and insistent voice."
He credits outgoing president Richard P. Campbell for bringing
these issues to the forefront and plans to prioritize focusing on
the needs of members, because if a trade association doesn't meet
the needs of existing members, it won't attract new ones.
In the court system, a significant pressure point to address is
the increasing number of pro se litigants who either can't
afford an attorney or choose not to have one. In probate and family
court and in housing court, 70 percent of the litigants are pro
se. Emergency litigation that needs immediate attention
increases the wait time for the more straightforward cases. The MBA
can help address the situation by exploring ways to reduce the wait
time, expense and tension of these overstretched courts.
Holloway commends Campbell with stressing the importance of a
sound legal system to an open and free society. The U.S. court
system is the world's best, he says, and it's modeled on the
Massachusetts court system, which came first. Technology has made
great strides in reducing the number of staff needed to support an
attorney from 3:1, 20 to 25 years ago, to one staffer for every two
attorneys today. That said, he cautions that the legal profession
Walter Costello notes that an effective MBA president has to be
able to grow into the position, and that Holloway "clearly has
brought himself up to that level."
Music to clear the head
Clarkin notes Holloway's versatility in the many aspects of
commercial law that his firm handles, such as tort and contractual
disputes. Holloway says this multidisciplinary reach gives him
constant opportunity to solve new problems and to remain outside a
comfort zone, a state of being which he prefers.
That's where music comes in, as an ability to clear out all the
pressures of the legal profession and to focus on something else.
"You get lost in it; it's a great way to clear your mind," he says.
He cites Boston as a hotbed of accomplished musicians who are
relatively unknown outside their respective circles. He has played
with musicians such as Jesse Williams, whom he cites as the best
bass player one could find, and keyboardist Bruce Bears, who has
accompanied blues great Duke Robillard. But he mostly goes solo due
to the logistical challenges of keeping a regular band
Clarkin has attended many rock concerts with Holloway, including
a memorable one at the Orpheum in Boston in 1988 that featured
Rolling Stones guitarist Keith Richards' then-side band, the
Expensive Winos. They found themselves sitting next to Steve Morse,
then a music critic for The Boston Globe, and they all agreed it
was "one of the greatest concerts we'd ever see."
Sheff, himself an avocational drummer, says Holloway's
proficiency in music serves to remind his colleagues that there's a
world outside of law.
Attorney Denise I. Murphy of Rubin and Rudman LLP in Boston
works with Holloway on some serious matters. She characterizes him
as dedicating himself to learning everything about the issues at
hand. "He's fully vested in anything he undertakes," she says. At
the same time, "He's a gifted musician, he has fun, and he's
infectious that way." When a colleague's son graduated from the
Berklee School of Music in Boston, Holloway hit the keyboards with
Holloway has played at two MBA officers' receptions and at
weddings, including that of a niece in Bridgewater last October - a
wedding over which he officiated, as well, obtaining a one-day
license to do so. "I was a full-service uncle that day," he
Music in the family
Holloway has been married for 43 years, and has a son and a
daughter, as well as a 2 ½-year-old grandson.
His son works in the investment business, but also plays regular
and bass guitar, and keyboard. His daughter is currently in Chicago
working on President Obama's re-election campaign. Holloway says
his office's proximity to home resulted in his being able to spend
more time attending his children's activities as they were growing
Both grown children have an interest in music and his grandson
is showing signs of interest, too. If you sit a small child at a
keyboard, he says, "some will pick out notes and others start
banging." His grandson falls into the former category. "If kids are
exposed to music and have any interest, they'll get involved," he