What I’ve Learned

Lesson 1: Try Cases

So, I learned: If you want to be a litigator, try cases.

Now, everyone knows that civil cases don’t go to trial very often. But litigators of every type, including appellate specialists, benefit enormously from first-chairing jury trials. Through trials, we learn what works in the courtroom and what doesn’t. We learn from our mistakes. Everyone makes them; some can be doozies. We can’t obsess over them, but our goal should be to learn from them and not to make the same mistake twice.

Also, if we are in court enough, we begin to see the rules of evidence as an essential part of our toolbox. And through trials, we eventually lose any fear of going to trial. It’s critical to lose that fear, especially when it comes to negotiating settlements for clients. If we’re apprehensive about going to trial, we’ll go to great lengths to avoid trying cases.

The best way to overcome that fear is to first-chair lots of trials, and the best way to first-chair lots of trials is to be a prosecutor or public defender. While that statement has some hyperbole, it doesn’t have much. If you see litigation in your future, seriously consider one or both of those jobs. You’ll learn a great deal, you’ll perform an enormous public service, and very few law firms will say to you later, “Sorry, but you’ve only first-chaired 25 trials. We’re not interested.”

Lesson 2: You’re Not Always Right

After about two years in D.C., I transferred to the Hawaii U.S. Attorney’s Office. Because we then were such a small office—just five or six AUSAs—I handled my own appeals. I was responsible for the Federal Bureau of Investigation (FBI) docket, which included lots of fraud and violent crime cases, the latter because there are many federal reservations in Hawaii. I also tried interesting civil cases, including medical malpractice cases, though there are no juries under the Federal Tort Claims Act.

One of the many murder cases I prosecuted was made into a TV movie: A Matter of Justice. The movie was conceived by one of the defense attorneys and starred Patty Duke and Martin Sheen. Sadly, neither played me.

Looking back on my time as an AUSA, I realize that for much of it, I suffered from the unfortunate mindset that I was nearly always right. Given that I was young and inexperienced, I should, of course, have felt quite differently. And that unfortunate attitude informed my approach to plea bargaining. “I don’t agree,” I often said. “That’s why we have juries.” I went to trial a lot.

So, I learned a second lesson, in all its variations: I wasn’t always right. None of us is, and we shouldn’t act as if we are. Better to go into every case with the view that we may learn that we’re wrong about some very important things.

When I left the U.S. Attorney’s Office for private practice, a federal judge who was one of my mentors gave me some valuable advice. “Mark, judges trust you, because they know that you will always be completely candid with them, even if that candor hurts the government’s case. You’ll find different pressures in private practice. Always remember, the reputation a lawyer spends a lifetime building can be lost forever in one moment.”

That sound advice has many corollaries: If something seems wrong, it likely is. Don’t sail too close to the wind. A career is a long journey, not a sprint. Always do the right thing. Clichés perhaps, but apt nonetheless.

Arriving at my first law firm, I couldn’t quite lose being a prosecutor. When the Honolulu prosecutor had a conflict, I prosecuted pro bono two murder cases, including Hawaii’s only Crip-Blood murder prosecution. That and some white-collar matters aside, almost all of my work in my 20 years as a partner at two Honolulu firms was civil litigation, including representing many government clients. Many differences from always representing the United States. For one, I didn’t have the FBI on my team to do the investigations.

Lesson 3: Listen More

Something else I learned: Listen more; talk less.

Other people have very valuable perspectives. We never benefit from them if we never give others the chance to express them or when we just ignore them. While that may seem to be spectacularly elementary, it took me far too long to learn it.

Lesson 4: Winning in Context

Another important insight I learned: We need to understand what winning means for each case and in the context of each case.

In the criminal case arena, it’s often pretty easy to define victory. In the civil arena, it’s much harder. For example, winning extended, expensive discovery battles at best marginally increases the chance of a better settlement or perhaps the chance of prevailing at an unlikely trial. For most clients, that’s not a real victory. Litigators should pick their battles with their client’s ultimate goals in mind.

After more than a decade in private practice, I was selected by Hawaii’s first Republican governor since statehood, Linda Lingle, to be Hawaii’s attorney general (AG). In Hawaii, that’s an appointed position, subject to state senate confirmation, and, as in most states, the attorney general is the chief legal and law enforcement officer of the state. I headed a department of around 700, including about 180 lawyers, and served for eight years, twice unanimously confirmed by the state senate, becoming the longest-serving Hawaii attorney general.

Oh, the lessons I learned. I was a Republican attorney general in a state with a legislature then about 20 percent Republican. Today, it’s about 10 percent.

Lesson 5: Be Open to Other People’s Ideas

So, speaking from experience: The attitude of “my way or the highway” often leads to the highway.

Of course, that’s always a bad attitude to have, but it can be surprising how prevalent it is. When we are truly open to other peoples’ views, ideas, and plans, we can accomplish so much more, including in litigation. As AG, it took me a year or two, but I learned.

Lesson 6: Our Word Is Our Bond

Something I always knew, but saw in a new light as AG, is this: Our word must always be our bond.

I continually saw in the political arena that those who stood by that principle accomplished far more than those who didn’t. Adhering to it gave me one of my more indelible moments as a litigator, when the Hawaii legislature hired me, years after I had left the AG’s office, to represent it as amicus curiae in a separation-of-powers case. See Nelson v. Hawaiian Homes Comm’n, 412 P.3d 917 (Haw. 2018).

When I was retained, the Speaker of the Hawaii House told me, “Bennett, one reason we’re hiring you is because all of us know that your word is your bond.” As a guiding star, that principle never fails—though I must also note that Judge King was fond of saying, “If someone says their word is as good as their bond, get their bond.”

Lesson 7: Loyalty

Before becoming AG, I did some supervisory work, both as an AUSA and as a law firm partner, but my focus always was on litigating. Then, as AG, I of course did far more supervising than I had ever done before. And another lesson emerged: Be loyal to those who work for you.

Loyalty doesn’t mean blind support or defending the indefensible. At least to me, loyalty means that if in the eyes of the outside world, including clients, it’s your case or ultimately your responsibility, and a mistake was made by someone on your team, it’s your fault—period. It’s not someone else’s fault, or no one’s fault, or sort of your fault. It’s just your fault. Never throw anyone under the bus, except yourself.

Lesson 8: Fear Motivates

I also learned that, while there are many good motivators, we never should overlook the power of straight and simple fear.

I had argued dozens of appellate cases, but never in the U.S. Supreme Court. While AG, I selected myself to argue two Supreme Court cases, Lingle v. Chevron U.S.A. Inc., 544 U.S. 528 (2005), and Hawaii v. Office of Hawaiian Affairs, 556 U.S. 163 (2009).

I was not the most qualified person to argue those cases, but part of the joy of being AG was that I could personally litigate some of the cases I thought were most important to Hawaii, and I knew that no one would work harder to prepare.

Of course, I wanted to win each of those Supreme Court cases, but my biggest motivator to prepare well was fear. I didn’t want to become a figure of fun on SCOTUSblog or, worse, in the press. In one famous exchange at the Supreme Court—where AGs often are addressed as “General” for no good reason—an AG noted that he had a fallback position. One of the justices quipped, “Well, General, then it’s time to fall back.”

Fear of something like that happening was a great motivator. In preparing for the arguments, I briefed literally hundreds of cases—probably the first time I’d briefed any cases since law school. I felt 100 percent prepared. Though that didn’t eliminate the fear, that fear was the single most effective motivator I’d ever had or experienced.

Lesson 9: Try New Things

Another lesson: We improve when we get out of our comfort zones.

We need to try new things, including new areas of the law. When clients shouldn’t be charged for the education, there’s always pro bono. While mastering a field is, of course, important, the more areas in which a litigator feels comfortable, the better the litigator. Virgil had it right—Audaces fortuna iuvat. Fortune favors the bold.

Further Lessons

I’ve continued to learn since becoming a judge.

Never discount the role of luck or fortune. Few of us were either born to the robe or are the reincarnation of Oliver Wendell Holmes. I wasn’t, and I’m not. Luck matters.

Becoming an appointed judge is, as one of my colleagues described it, akin to being struck by lightning. Still, if becoming an appointed judge is your goal, be prepared for the possibility that good luck may someday head your way. Work hard. Be the most ethical lawyer you can possibly be. Try cases. Argue appeals. Don’t be a jerk. Treat everyone with respect. Believe in karma.

As an appellate judge, I offer some strategic advice: Don’t bury the lede. Tell the court, right off the bat, what’s most important. Don’t start with something like, “Your Honors, I will make nine points today. First, let me list all of them for you.”

If something is bad for you, or even just arguably bad for you, be the first to get it out there. On appeal, that means disclose it in your brief, if you can. And be the first side to raise it. Of course, being the first to raise anything is harder for appellees, but use good judgment whenever you can.

Don’t minimize the real problems in your case. Far too much appellate argument time is wasted by lawyers poorly dancing around an issue, when they should have simply acknowledged the point or problem and moved on as best they could. If the court thinks you’re protesting too much in one area, that can hurt the rest of your case, even in unrelated areas.

Give the court the simplest way to provide you with the win that you need. The Rolling Stones absolutely had it right: “You can’t always get what you want. But if you try sometimes, you’ll find, you get what you need.” So be very realistic, and go with the flow of the argument.

As you know, shorter is usually better. And, of course, shorter is usually harder. Judges and law clerks pay more attention to very well-written shorter briefs. As part of shorter is better, if you are the appellant, your rebuttal should have only a few points, and each of those points should be brief and punchy. Keep it as simple and straightforward as possible.

Always have your goal of winning in mind. Try to ensure that everything you do leads to winning, or at least points toward it. Spending valuable minutes explaining why your adversary is wrong on an immaterial point doesn’t help achieve victory. And appellants simply can’t win unless they make it very clear why the trial court’s error or errors matter. Sometimes that’s obvious, but often it isn’t. That’s why so many opinion paragraphs start with the phrase that no appellant ever wants to see: “Even assuming there was error. . . .”

Finally, this: Half a loaf is better than none. Every oral advocate has argued a case in which it appeared very early on that complete defeat was heading his or her way. The best advocates recognize that while it’s happening and are sometimes able to turn absolute defeat into partial victory.

Fifty years ago, I gave an entirely wrong-on-the-merits high school graduation speech. It had one good part—the closing—quoting Robert Browning: “Ah, but a man’s reach should exceed his grasp/Or what’s a heaven for?”

Aloha.