Alumni Spotlight

Judge F. Dennis Saylor

Judge F. Dennis SaylorJudge Saylor was a summer associate at Goodwin in 1980 and then started at the firm as an associate in the fall of 1981. He left in 1987 to go to the U.S. Attorney’s Office in Boston, and then returned to Goodwin in 1993.  In 2004, he was confirmed by the Senate as a Federal Judge with the U.S. District Court for the District of Massachusetts. Read more to learn about Judge Saylor’s current role and his greatest takeaway from Goodwin.

If someone would have told you when you graduated law school that you would one day be a Federal District Court Judge, what would you have said to him/her?

What I probably would have said is not printable. I certainly would have been surprised. I never dreamed it would happen.

What are three things that everyone should know about you (personally and professionally)?

First, as a judge, that I don’t have an agenda. I’m trying to do the right thing—to follow the law, to be diligent, and to reach the right decision. That’s a lot harder than it looks. Second, that I remember what it’s like to be a lawyer. I try to accommodate lawyers’ personal lives and their schedules. I often let people appear by telephone. I try to work around their vacations when I’m scheduling things. I have issued an order trying to encourage more junior lawyers to appear in court because I think that’s important. Third, that I have outside interests. I love my wife and family. I take my own vacations. There are other things that I want to do with my life, other than being a judge, and I think that’s also important.  

Do juries get it right? 

I think juries usually get it right if they’re properly instructed and guided by the judge. Part of that is following the rules of evidence and the law. Trying to make sure the jurors understand the law is very important. I give all of my jurors written copies of the instructions. If there are 12 jurors, there will be 12 copies of the instructions. I have them read it with me as I read it out loud. Their comprehension level is several orders of magnitude higher than it would be if I just read it to them. Hardly any judges do this, but I think it’s critically important. If you want people to understand the law, give it to them in a way that maximizes their comprehension. The way I do it, they can re-read the instructions. They can take notes on them. They can take them into the jury room. You can’t expect a jury to get it right if you don’t give them the basic tools to do the job.

What is the best aspect of your job and what is the most challenging aspect of your job?

The best aspect of my current job is just about everything. The most challenging aspect is keeping up with the work. I have a very passive job. I don’t go out looking for work—the work comes to me, whether I want it or not. The conveyor belt, metaphorically speaking, just drops it off. I have to keep up with it, make sure I’m staying on top of things, moving it along.  Sometimes, the result is less than complete perfection because you just don’t have enough time. But it’s a great job. It’s interesting, it’s fun, and I work with great people.  

Any advice for those considering a career in public service or any other alternative to large firm practice?

I feel that I am a much better judge because I had experience in both private practice and public service. On the criminal side, I was both a prosecutor and a criminal defense lawyer. You learn a lot doing both. I think I was a better defense attorney having been a prosecutor and a better judge having been both. If you have the right opportunity and you can afford it, I strongly encourage people, particularly litigators, to go back and forth across the line between private practice and public service.  

In what ways have you seen the legal profession change over the course of your career?

Big firm practice has certainly changed. When I started at Goodwin we were only a Boston firm.  For some stretch of time we were the largest firm in America without a branch.  We often had what I would call vertical relationships with our clients. For example, there would be a company headquartered in New England and we would do everything for that company. We’d do the corporate work, the tax work, the real estate work, the labor work. There would be litigation, big cases and little. There is very little of that anymore. It’s now a horizontal relationship that is more specialized. One advantage of the vertical relationship is that there would be small matters for junior people to handle. My first trial was a bench trial for a client of the firm. It involved about $10,000. The client was this rich and grumpy and stubborn guy who basically told me he would never settle—those weren’t his exact words, they were a lot more blunt than that. I went to trial and I won. I was all by myself. It was good training for me to be out there on my own. It’s too bad that that aspect has been lost.  

Another obvious change is technology, which has made lives both better and worse. I’ll focus on one of the negatives, which isn’t limited to the legal profession. Nowadays, everyone is on call all the time, whether it’s 6:00 a.m. on Sunday morning or you’re on the beach in Bermuda. It used to be that if you went on vacation to Italy for two weeks in August and a problem came up, either things would wait for you when you got back or they would deal with it while you were gone. Now, if you say you’re going to Italy for two weeks, they say that’s fine, but the conference call is at 7:00 p.m. your time. Call us from Venice. I think that’s a shame. I think it degrades the quality of people’s lives, particularly junior people. One of the great things about being a judge, by the way, is I can go away for two weeks and no one tells me I have to be on a conference call.

Any advice for lawyers starting their careers?

That they should make an effort to find good people to work with and interesting things to work on. Jeff Dando, who was managing partner at Goodwin for many years, used to say that no one cares about your career as much as you do. I think it’s a real mistake if you sit at your desk and wait for your career to happen to you. Maybe you can’t manage it perfectly, but you can get good work sometimes just by being enthusiastic and volunteering. New lawyers should also know that it’s always hardest at the beginning. That’s when you’re most confused and making the most mistakes. It does get better over time if you just stick it out. And, if you somehow get yourself in a position where you’re not really happy, well, make a change. Don’t be afraid.

How did your training at Goodwin Procter prepare you for what you’re doing now?

I had a great experience at Goodwin. I worked with excellent lawyers and had interesting assignments right from the start. I did a lot of work with Pete Simonds, who was probably the best trial lawyer that I ever saw. I also worked with Allan van Gestel, Sam Hoar, Paul Ware, Brackett Denniston, and a lot of other talented lawyers. I received excellent training at Goodwin. We had an in-house trial training program that we had to do every year and I learned a great deal from that, which helped me a lot when I started to try cases. I’ve always been grateful to the people who were willing to give me some responsibility, to train me and then let me go out and actually do things in court.

What are some of your fondest memories from your time at Goodwin?

I remember when I was a young lawyer, helping to write the briefs in a case that was argued by Allan van Gestel on the Supreme Court concerning Indian land claims. I was two years or so out of law school and I had a very significant role.  

I had some interesting trials. I represented a Kuwaiti woman accused of slavery in federal court. I represented an accused Soviet spy in a long trial, also in federal court. Both cases ended in mistrials and both were never retried. I like to say that my record in slavery and espionage trials is 0-0-2:  no wins, no losses and two ties.  I never lost a case—although I never won one, either.  

I had an internal investigation with Mark Pearlstein, who is a very good friend of mine, and who’s now at McDermott, Will and Emery. We traveled a lot to New Orleans with associates from another firm. That was a lot of fun. 

One of the things I liked about Goodwin was that we had a lot of fun, more so I think than other comparable firms. I had a lot of friends and we were all kind of iconoclastic, and maybe a little sophomoric.  

What is your best takeaway from Goodwin? How is the firm still part of your life today?

My best takeaway from Goodwin is my wife, Addie Fiske. She’s a Goodwin alum, although we didn’t overlap at the firm. I’m still friends with a lot of people at Goodwin—Tony Fiotto, Jim Rehnquist, Robbie Braceras, Kevin Martin, John Daukas, really too many people to list. Plus a lot of alums. Maureen Shea, who I’ve known for more than 35 years, is a good friend. I see Goodwin people all the time. It’s a very big part of my life. 

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