A Trust and Estates lawyer’s ‘last lecture’: ‘Hope for the best; plan for the worst’

“Hope for the best; plan for the worst,” Harvard Law School Professor Robert Sitkoff told the audience on March 29, in his contribution to the Last Lecture series. Sitkoff, an expert in trusts and estates, wove the trusts and estates motto throughout his speech as he explained the importance of private law in helping individuals organize their lives.

The Last Lecture Series, which is organized by the Class Marshals, asks popular HLS professors to give lectures addressing the graduating class. This year’s series has also featured Professors Jeannie Suk ’02, Annette Gordon-Reed ’84, and Robert Bordone ’97.

Sitkoff said his main goal was to speak about private law, as distinguished from public law.

You are the lawyers. You are in a sense the public servant, but here as a guardian for the law that governs people in their most intimate relationships.

Robert Sitkoff

Public law is “the law that people think about with law; that’s the law that’s on the cover page of the New York Times,” Sitkoff said. “But that’s not the law that many of you are going to practice, and that’s not the kind of law that is impactful on people all the time in their interactions with other people, their most fundamental relationships.”

Instead, Sitkoff wanted to talk about private law and “the kinds of laws that enable people to order, privately, their lives and relationships with other people.” Private law is the subject of his teaching and practice, and it’s that subject, Sitkoff said, that most HLS graduates will encounter as they enter private practice and work in areas such as corporate and family law.

In private law, one vision of what a lawyer does is to act as a “transactional cost engineer,” he said. Clients have purposes and policies that they’re trying to achieve, and it is the job of lawyers to “understand that and to use these tools…to get at what they’re trying to do.”

Sitkoff raised the hypothetical of a couple who wish to marry later in life. A lawyer’s role in that scenario would be to craft a premarital agreement that changes default rules to meet the couple’s needs, such as heading off any inheritance disputes between stepchildren.

Robert Sitkoff

Credit: Martha Stewart

“There’s this feedback loop between what law and the lawyers were doing to achieve the purposes of the client,” Sitkoff said. “If you anticipate this in advance, you will help your clients achieve their private ordering goals, without a perverse incentive that will undermine the purpose for which they’ve come to you, which is for help in ordering intimate, critically important things to their happiness.”

Sitkoff said his own life experiences taught him the importance of private law. From a young age, he received a theoretical understanding of estate planning from his father, a trusts and estates lawyer.

“Some of my friends, they’d go play ball with their dad; we’d play ‘kill the client’s family,'” Sitkoff joked, describing how he and his father would draw the client’s family tree and make sure the legal documents provided for every contingency.

But the games became real when Sitkoff’s mother died of ovarian cancer when he was a 17-year-old high school student. Sitkoff had always typed wills for his father’s busy law practice, and then one of the wills he typed was his mother’s. He also saw how his father’s will and guardianships and trusteeships were set up to ensure his younger brother would be cared for.

“For some people, this sounds like a grisly, gruesome, sort of horrible thing. For me it was a source of extraordinary comfort,” Sitkoff said. “For me it was a sense of, I’m going to hope for the best, that my mom won’t die. She did. I’m going to hope for the best that my dad won’t die any time soon, but it could happen.”

“‘Winter is coming,'” Sitkoff said, lightening the mood with a Game of Thrones reference. “I know, I have experienced it. It could happen. Bad things can and do happen.”

One of the roles of lawyers practicing private law is that you have to be the one to say, bad things happen and we have to plan for that, he said.

Sitkoff also talked about his career trajectory. When he was choosing a law school, he recalled, several professors “aggressively, heavy-handedly” arm-twisted him to attend the University of Chicago instead of Stanford.

“One of them said, ‘Write this down. Mark my words. Go to Chicago; you’re going to take in law and economics; you’re going to get a good clerkship and then you’re going to teach. This is your first best destiny, sort of obvious, this is what you need to do,'” Sitkoff said.

As it turned out, the professor was right. After law school, Sitkoff clerked for Judge Richard Posner on the Court of Appeals for the Seventh Circuit. He described telling the celebrated judge about some of his ideas, noting that “one worry about these ideas when nobody else has done it, nobody else has seen it, is that you’re just nuts.”

Following encouragement from the judge, support from University of Chicago Professor Lisa Bernstein, and a fateful Passover seder, “next thing I knew, I was giving a presentation to the faculty, and they were voting to give me a tenure-line appointment,” Sitkoff said. And so he went to Northwestern University, where he turned 26 the day before teaching his first contracts class.

Through his research and writing, Sitkoff came to the realization that “people are changing their private ordering in light of how we are changing these rules.” Once he was convinced that the rules really mattered, he decided that in addition to teaching and scholarly work, he wanted to start thinking about law reform.

Sitkoff criticized what he sees as an “undue emphasis” among law school programming and leadership “to denigrate private law work and to suggest that the only meaningful work for lawyers in contemporary society is in reworking public law in a public interest sort of way.”

“I don’t think that’s right empirically. I don’t think that’s right normatively,” Sitkoff said. “I’m telling you I know—I know in my heart, I’ve lived it—the importance of private law and private ordering for individual lives,” he said. “And in my scholarly life, I found out, it was right in my face, that this really matters. It’s changing the way people organize their lives when we change these rules.”

Organizations like the Uniform Law Commission and the American Law Institute are particularly relevant now, Sitkoff said, because they bring together “a national level of experts to pool its understanding of problems and to say, ‘Here’s a new development in practice, in technology or whatever, and here’s how we can change our rules so that people can do their private ordering in an efficacious sort of way.'”

Sitkoff said graduating students are going to develop expertise in various areas of private law, and they will invariably encounter limitations in the law, where they find that the law is at odds with the outcomes people are trying to achieve. “It will be your responsibility to fix that,” he said.

“You are the lawyers. You are in a sense the public servant, but here as a guardian for the law that governs people in their most intimate relationships.”

Why is that job important? “Because this is private ordering, this is private law, these are our most intimate relationships,” Sitkoff said. “If you’re a lawyer, and this is what you do, this is essential for civil society.”