A federal judgeship is, by almost any measure, the proverbial opportunity of a lifetime for those in the legal profession — figuratively and quite literally; one has the job for life. So it is with Mark Mastroianni, although he admits that he became a candidate for the post in Springfield almost reluctantly because he was, at the time, “hitting his stride” as Hampden County district attorney. In fact, he admits feeling relieved in some ways when he missed the deadline for applying. But that deadline was extended, and, well, the rest is history — and a serious period of adjustment that is still ongoing.
Mark Mastroianni was talking about the start of the process that eventually led to him being named a federal judge in Springfield.
To describe it, he used the phrases “completely unexpected” and “perhaps even unwelcome.”
He said it was the former mostly because at that time, early 2014, he was more than halfway through his first four-year term as Hampden County district attorney and thinking about the next one, not a new career challenge.
As for the latter, he chose it because he wasn’t simply serving as DA. He was, as he put it, “just hitting my stride,” and in many ways he actually resented what the ensuing search process represented — an extremely difficult decision he would have to make about his career, or another difficult decision, to be more precise.
“I was three years in the district attorney’s office; I was getting my feet under me and really developing my sense of confidence,” he explained. “And it’s really at the point when you develop a sense of confidence doing anything that you become your most effective. I had things to do — I had things I knew I could do in the district attorney’s office that were important for me as professional accomplishments and for the people I was serving.
“I really took to that, and was serious about what I wanted to do,” he went on. “And when I say ‘unwelcome,’ I say that because that search came about right when I got moving.”
But there was more to this than the opening on the federal bench coming at what Mastroianni would consider the wrong time career-wise. Indeed, he possessed vast experience as both a prosecutor and defense lawyer at that time, and frankly couldn’t imagine himself spending at least the next 15 years (a federal judgeship is a lifetime appointment) being neither.
To get that point across, he put his passion for such work in perspective that only people who have been there could appreciate.
“There will be nothing like — at least, I haven’t experienced anything that looks like it will be the same as — the adrenaline rush in a capital murder case in the minute or two minutes when you’re waiting for the verdict,” he said while comparing his current job to his previous ones. “The jury comes in, the jury stands up, and the verdict form is handed to the clerk … I can’t explain to you what that’s like, really. Every trial I’ve taken, it’s been remarkable to me that I’ve been able to even stay on my feet; your heart is beating so fast, you just think that physically you’re not going to hold up.”
One doesn’t reach that state, emotionally or physically, as a judge, he went on, adding quickly, though, that adrenaline comes in many forms, and he experiences it now — granted, on a much lower level — when one of his rulings is cited by a lawyer when making an argument.
Adapting to this new standard for adrenaline rush is part of an adjustment period Mastroianni says is still ongoing, although overall, he says he’s quite comfortable in his new skin, or robe, as the case may be. He acknowledges that reaching this state wasn’t easy, but in most ways easier than he anticipated.
“I have been so happy and relieved at how I’ve adjusted, because I thought that I was going to really struggle with not being in the courtroom,” he said, referring, obviously, to the seats in front of the bench, not the one behind it. “I have really enjoyed and adjusted to still being part of the trial-litigation criminal process; I take a different seat now than the one I’m used to sitting in, and my decisions are from a different perspective, but I’ve adjusted, and continue to adjust.”
For this issue and its focus on law, BusinessWest looks at that adjustment period, and how it represents one of many career gambles Mastroianni has not only taken, but embraced.
When asked about whether he had any regrets about taking the federal judgeship, Mastroianni answered in a way one might not expect from someone in such a lofty, respected, and sought-after position.
“Of course I have regrets,” he said, implying that some of his earlier comments would have made that clear. But he went further, and in a manner that once again suggested just how much he liked being DA — and a defense lawyer, for that matter.
“I’ve had regrets from every job I’ve left,” he explained. “If you don’t have regrets from the last job you’ve left, that means that didn’t love your job and didn’t do it with everything you had.”
Mastroianni has left a few positions in his career knowing that there would be not only regrets, but serious doubts from colleagues, friends, and relatives about whether he was doing the right thing, career-wise and otherwise.
There were such sentiments expressed when he left a position as assistant district attorney under William Bennett to go into private practice. He had started a family and purchased his first house, and while prosecutors were poorly paid at the time (and still are today), the job represented a safety net.
He heard them again when he launched a bid to succeed Bennett as DA running as an independent, a campaign for which for which the adjective ‘long shot’ would be considered a serious understatement.
And they were uttered again when Mastroianni became a candidate for the federal court, a position usually placed in that category of ‘opportunity of a lifetime.’
“Every friend and family member expressed the concern that it would be something I might not enjoy or become frustrated with,” he noted. “I had that same concern.”
Mastroianni said he made these various career moves after careful consideration of those expressed concerns, but also what the next challenge would mean for him personally and professionally.
“These were not reckless decisions,” he explained, using that phrase repeatedly with his latest change especially. And as he talked about them, he would reference a need to continually seek new challenges because “there was more for me to do.”
Our story begins at Cathedral High School in the early ’80s, where Mastroanni was mostly unmotivated and anything but a standout student and rising star. In fact, he would say that American International College “took a chance on me when they accepted me.”
He made the most of that opportunity, though, majoring in English and political science and contemplating careers as a writer or journalist while doing so. But he chose a different tack — one encouraged by his grandfather — and enrolled at Western New England University School of Law.
Upon graduation from WNEU in 1989, he found himself in a tough job market as a recession that would last the better part of half a decade settled in on the region. He borrowed money from some family members and opened a private practice in the same building in Springfield’s Court Square that his grandfather practiced from.
But the phone didn’t ring much, and he eventually sought to fill an opening on the staff of then-Hampden County District Attorney Matty Ryan. That assignment lasted only six months, as Ryan’s eventual successor, Bennett, did not keep him on after assuming office.
However, Bennett later rehired him, and he worked five years as an assistant DA, cutting his teeth on a number of high-profile cases, including several murder trials. Despite his success in that role, he sought another challenge — and potentially much larger paycheck — and returned to private practice.
He would remain there for 17 years, enjoying success on the other side of the legal system — defending clients — and on the all-important business side of the equation as well.
Eventually, he became as passionate about defense work as he was with his prosecutorial skills, and when pressed to compare and contrast the two, said that he found the former in some ways as rewarding professionally as the latter.
“What I like in both of them is high-level, high-profile, difficult cases,” he explained. “There’s an enormous sense of satisfaction that comes with successfully prosecuting a case and helping victims. But, quite frankly, I think that feeling is rivaled, and perhaps equaled, by the sense you get in the successful defense of a case and being the person who stands between one individual and the government, the prosecution, and the resources of that prosecution.
“With the murder cases I handled, there were primarily appointed cases — it’s one individual who’s been deemed to be indigent; we’ll appoint you a lawyer, and there you go, good luck with that,” he continued, explaining, in more detail, that sense of satisfaction he enjoyed from helping clients prevail in such matters. “You have a limited budget and limited resources, but there’s no limit to energy and effort you can put in.
“The satisfaction is not of ‘I want to help someone get away with something,’ or ‘I want to pull one over on someone,’” he went on. “The satisfaction is working within the system and making the system work; our system means nothing if there’s not vigorous defense work forcing the government, be it the Commonwealth or the federal government, to meet their burden of proof. Every good defense makes the next prosecution better.”
He said that, if he were ever put in a position of having to choose between the two, that would be a very difficult decision. So it’s fortunate, perhaps, that circumstances now mean he won’t have to make such a choice — at least until he turns 65.
As he talked about his career and the many twists and turns it has taken, Mastroanni referred early and often to the notion of timing, and how certain events — from a recession to the retirement of a federal judge — have played a big role in shaping his many difficult decisions.
One such point in time was Bill Bennett’s decision to not seek another term as DA in 2010 after 20 years in that office.
Mastroanni admitted he was already thinking about pursuit of new and different challenges at the time, but Bennett’s decision in some ways forced his hand — again, amid concerns from collegaues and family members that he might be making a big mistake.
“The question from friends and family was, ‘why? What are you doing? … you can’t walk away from this,’” he said, referring to the very successful private practice he had built. “At that point, it was something inside me professionally — a need to do more. It was this reflection, this self-examination of where I was, where I wanted to be, and what I wanted to be doing that led me to run.
“I wanted a challenge, I wanted a change, and I really felt I could do a good job as district attorney,” he went on. “I had very specific ideas about the criminal-justice system and how it could work better.”
But while he had the will to seek the post, he wasn’t exactly dealing from a position of strength, at least to most observers.
Indeed, while the DA’s position is non-political by nature, the processing of winning is quite political, and Mastroanni, upon entering the race, also decided he would wage his fight as an independent. That choice would impact everything from his participation in scheduled debates to raising money, but he stuck to his guns and eventually prevailed.
In the winter of 2011, he settled into the job — or at least the part he wanted to settle into.
He admitted that he had no real appetite for what could be called the operations side of the office — the budgetary matters and many aspects of managing 150 people and several offices. So he effectively delegated — something he says isn’t easy, and is an art form unto itself.
“That was like running full-speed into a brick wall when I encountered that administrative setup at the district attorney’s office,” he told BusinessWest. “You have a lot of employees, an IT team, a state police squadron assigned to you … so I delegated. I had to choose what to delegate, and I chose not to delegate the trial work; I thought I was certainly more qualified and competent as the trial lawyer who could take on the big case than I was as the person who would walk in and take care of the budget.”
Thus, he focused on trying cases (one of his first involved a successful prosecution in the murder of Cathedral High School student Conner Reynolds) and myriad other aspects of a very broad job description.
That list included everything from making progress with a large list of cold cases to going out into area classrooms and providing lessons on how the judicial system worked.
“We opened new units — we opened an unsolved-crime unit and a DNA unit, and we made really big advances in some cold cases that had not been worked on in some time,” he explained. “We solved several cases that were 20 years old and more. I developed a way to use drug-forfeiture money to essentially pay for the overtime so police officers could work on these cold cases.
“Springfield has so many unsolved cases, and one of the reasons they’re unsolved is because new cases keep flooding in every day,” he went on, adding that he developed a process by which trained individuals could devote the needed time, energy, and imagination to such cold cases. And many wound up being solved.
“That program was cranking,” he continued. “Meanwhile, our community outreach was just unprecedented; we were in the schools with all kinds of programs … it was wonderful, challenging, stressful times at the district attorney’s office. That’s a difficult job, and I was really enjoying all the progress we were making.”
It was at this point that the unexpected and “perhaps even unwelcome” search for a successor to the retiring Judge Michael Ponsor commenced in late 2013.
Then-recently elected U.S. Sen. Elizabeth Warren was placed in charge of the process of selecting a new federal judge, said Mastroanni, who said he had no intention of pursuing the post until he was encouraged to do so by members of the Gertner Committee, a panel appointed by Warren to solicit, interview, and comment on applications for federal District Court vacancies, and so-named because it was chaired by former District Court Judge Nancy Gertner.
Although he entertained those entreaties to become a candidate, Mastroianni admitted to feeling what amounted to a sense of relief that he missed a posted deadline of Jan. 31, 2013 for submitting a formal application.
“In my mind, how a lot of things work is that I’ll put things off as long as I can, and if I just put it off long enough, it will just take care of itself,” he explained. “I put that into practice with my judicial application. Before I knew it, the deadline had come and gone, and I didn’t get my application in, and I said to myself, ‘that’s too bad … I’ve been so busy as district attorney, I didn’t have a chance to fill this out. It’s just not right; I’m too busy as D.A. This is obviously where I should be.’”
As fate would have it, though, the deadline was extended, and Mastroianni would apply and eventually get the nod after many strenuous rounds of interviews.
When asked to analyze that result and how it came about, he would theorize that Warren was seeking diversity from the next federal judge, not only in the context that one might think, meaning racial or gender diversity.
“I think they thought my political affiliation — choosing to be an independent — as well as working at the highest level on both the prosecution side and the defense side gave me a rather unique perspective and view of the world and the legal system.”
With that perspective — and that résumé detailed above — Mastroianni entered his new role and adjustment period with that degree of trepidation he noted. But he has, in fact, found a comfort zone.
“I knew during my first couple of trials that the adjustment was going to be OK — I wasn’t feeling the need to look at the case that was developing in front of me as the trial lawyer,” he said, adding that he anticipated that being able to do so would be a sizable challenge. “I was not substituting myself for the lawyer in question; I was appreciating the art of trial work, and I do consider it an art.
“I found the challenge of presiding over that and watching how it develops to be so exciting, and so new,” he went on, adding that, while he’s observing and analyzing what the lawyers handling the case are doing, those opinions don’t manifest themselves in words or actions in the courtroom.
“I’m perfectly happy and content with thinking in my mind about what that lawyer does and saying to myself, ‘how could you have done that? What you really needed to do was this,’ or watching a lawyer do something just perfectly and thinking, ‘that was well-done.’ For me to interrupt lawyers and try to make arguments for litigants and try to control how a case goes, that would be going overboard and not being well-suited to be in my position.”
The period of adjustment has other aspects to it, he said, noting, for example, that most of the cases that come to him are civil in nature, while most of his direct experience is with criminal matters.
Overall, though, while Mastroanni had some concerns about whether he could make an easy adjustment to a life of hearing arguments rather than presenting them, he was confident (there’s that word again) that he could do the job and do it well.
“I knew that I could rise and meet the challenges of this job knowing that I would have regrets,” he said. “But I’m adjusting, I very much like what I’m doing, and the forecast looks good.”
He’s even making the time to go into area classrooms and provide lessons on the legal system, as he did when he was DA, and will begin teaching a class in civil law at his alma mater this fall.
As for adrenaline, well, he still gets to experience those rushes, only in much different ways.
“I’m getting an enormous amount of satisfaction from seeing cases that I take develop, crafting the law as I see it applying to facts, and ultimately doing justice in terms of doing the right thing,” he said in conclusion. “That’s really what we do, and that sense of satisfaction from seeing a case come in, taking it from the beginning, working with it, and leaving here having made law, effecting law in a way that other cases that come after you are going to cite … that’s not the same kind of adrenaline rush I described while waiting for a jury to return a verdict, but that’s a satisfaction and type of rush that’s very, very rewarding.”
While Mastroianni maintains that he’s successfully adjusted to life on the bench, he nonetheless wishes he could somehow keep this job and experience all those emotions he mentioned when talking about that moment when the verdict is read by the jury foreman.
“I would absolutely love and welcome if there could somehow ever be a setup where I could try a case again,” he told BusinessWest. “That would be like the fantasy football league for me; that would be absolutely it.”
Such a setup isn’t possible, though, and Mastroianni understands that he’ll have to wait until he’s at least 65 to even think about being back on the other side of the bench.
For now, though, he’s focused on that new standard for adrenaline rush and finding new ways to experience it.
As he said, this is an adjustment period that is still ongoing.
George O’Brien can be reached at firstname.lastname@example.org