Of failures and comebacks: A Dean’s story

Douglas Sylvester
Most people avoid admitting “failure,” using terms like “setback” or “wrong turn.” But Dean Douglas Sylvester thinks people should embrace it.

“I reject the view that anyone is a ‘failure,’ ” Sylvester said. “But that doesn’t mean we, as individuals, don’t fail. We all fail. There are times when we make mistakes, don’t give our absolute best, or just don’t achieve what we know we can. But failure is not an end.”

Sylvester has overcome many hurdles and expects to face more. His life can be seen as an example of perseverance leading to the success of a challenging career with great responsibility and fulfillment.

“My path to becoming dean is not a normal one,” Sylvester said. “I have not had a string of clear upward moves. I’ve failed at many of the things that one would expect are necessary to succeed in this profession.

“But I’ve always used my failures as lessons or as opportunities to seek a different path. Failing, for me, is recognizing that I can do better but also recognizing that failing can be a beginning. For many new lawyers, knowing that how you start out is not always where you will end is, I hope, an important aid.”

Sylvester was born in Youngstown, N.Y., a small town on the mouth of the Niagara River and Lake Ontario. His parents, both Canadians hailing from British Columbia, had come to the United States to pursue his father’s academic career. His father, Bernard, was a philosophy professor at a small liberal arts college, Niagara University, near Niagara Falls.

Sylvester’s mother, a homemaker while he and his brothers were young, went back to school earning bachelor’s and master’s degrees in education and, for a short while, taught in a local school. She later ran the religious studies program at the local Catholic church. When he was 11, he lost a younger brother to leukemia. He has two other brothers, one (Kevin) an illustrator, author, and radio broadcaster in Canada, and the other (Tim) working for FedEx in Buffalo.

“Youngstown was a great place to grow up,” he said. “It was right on the Canadian border so we were exposed to Canadian and American culture. I watched Second City Television as much as ‘Saturday Night Live’, Monty Python, old movies, CBS television, the Grey Cup and the Super Bowl. It was a bit of a melting pot for the 1970s.”

Sylvester did not graduate at the top of his high-school class, or even close. He was not a stellar student in college, at the University of Toronto, and wasn’t even sure about law school when he applied.

“The only thing I did really well in those years was meet my wife, Anna, at the University of Toronto.”

Sylvester with wife, Anna, and daughter, Darcy.
Anna, a fellow student at St. Michael’s College at the University of Toronto, graphic designer, and event planner, was born of Uruguayan parents and lived just outside Toronto. Bonding over old movies (their first date was to see Casablanca) and late-night coffees, they have been married for 18 years and have a four-year-old daughter, Darcy.

Anna said that first meeting was a set-up, and they were a perfect fit.

“We would sit around and talk for hours,” Anna said. “He had a sharp wit and a quirky sense of humor. He was always intellectually engaging, always the person who began the conversation. It was very comfortable. He was a warm, funny, nice guy, with a good heart.”

Sylvester’s decision to attend SUNY Buffalo School of Law, was a turning point in his academic career.

“I loved law school,” he said. “I quickly found I had an affinity for legal analysis and argument. I enjoyed moot courts and even law review. I really hit my stride as a student there.”

Professor Guyora Binder first met Sylvester in a law and humanities seminar Binder taught at Buffalo, when Sylvester was pursuing research in the history of the law of nations.

“It was great fun for everyone, in large measure because of Doug,” said Binder, SUNY Distinguished Professor and Vice Dean for Research and Faculty Development. “He read other students’ papers with so much curiosity and enthusiasm, he asked such penetrating questions and offered such helpful suggestions, and he sweetened it all with so much goofy, self-deprecating humor, that he inspired other students to emulate him.”

Binder said he was thrilled to have Sylvester as a teaching assistant the next year for a section of research and writing.

“Already a moot court director and managing editor of the law review, Doug had demonstrated a gift for inspiring and motivating other students,” Binder said. “He was predictably great, much more than an assistant, taking over much of the classroom teaching and spent endless hours meeting with students individually and in groups.

“His humor made the driest, most technical material interesting, and he made the writing and argument exercises so much fun that many students spontaneously did far more work than they were assigned. Indeed, students in other sections began to complain that they weren’t being given enough to do, to my colleagues’ considerable confusion.”

Binder said he has rarely met anyone who made the exchange of ideas and arguments so much fun.

“Doug’s performance as a TA foreshadowed the great success he would later enjoy not only as an outstanding teacher, but as a mentor and motivator of other faculty,” Binder said.

Sylvester did well at Buffalo, earning moot court honors, being appointed to the law review, and graduating near the top of his class. But, once again, the path forward was neither clear nor easy.

He landed a summer clerkship with one of the city’s largest law firms but, in the economy of the mid-1990s, was not able to turn that internship into a permanent offer.

“I would love to blame the economy,” Sylvester said. “But the real blame was with me. I just didn’t know how to make the transition from my prior jobs, as a line cook or janitor, into a professional environment.”

He interviewed with dozens of firms, applied all across the country, and failed to land a job upon graduation from law school.

“I was unemployed and, frankly, a bit lost about what to do next,” he said. “I already owed about $60,000 in student loans, and I made the decision to more than double that amount and take an LL.M. at New York University.”

That decision, made with the support Guyora Binder, introduced him to Professor William Nelson at NYU, and both of them urged Sylvester to pursue a career in academics.

“I’m still paying off that student debt—but it was worth it.”

Based on recommendations from his mentors, Sylvester landed a federal clerkship in Miami with the late C. Clyde Atkins.

“Working for Judge Atkins was a phenomenal experience,” Sylvester said. “It was transformative for me and, frankly, it was the place where I learned about professionalism, judgment, and what it really meant to practice law. I urge every student to pursue a clerkship. There simply is no better way to transition from student to lawyer.”

Following his clerkship, Sylvester wanted to pursue a career in academics but, with a degree from Buffalo and few publications, he knew going on the market would not be successful.

“I still wasn’t ready to teach,” Sylvester said. “I hadn’t published anything. I had no credentials.”

Although he applied for numerous short-term positions on law school faculties, he struck out on every one. Out of the blue, as he was ready to give up on the search, he received a call from Dan Kahan at the University of Chicago Law School inviting him to interview for the Bigelow Fellowship, perhaps the most prestigious fellowship available for those seeking to become legal academics.

“Douglas Sylvester is consumed by curiosity,” said Kahan, now the Elizabeth K. Dollard Professor of Law and Professor of Psychology at Yale Law School. “The opportunity to satisfy and rekindle his curiosity over and over is what has made ASU such a perfect place for him as a scholar and teacher.

“Now, fittingly, it is his curiosity that will reliably inform his judgment about how to help the law school maintain all the special qualities that have made it such a remarkable site for the production of professional craft and knowledge.”

Sylvester said the Bigelow Fellowship, his first full-time teaching experience focused his career path.

“I love thinking about how to explain something, how to convey the information,” Sylvester said. “Being on the faculty, well sort of on the faculty, at Chicago, was an incredible learning experience. Working with people like Dan Kahan and Jack Goldsmith was absolutely invaluable. My education, quite literally, never stopped after leaving law school.

“It was then that I knew that teaching was something I absolutely wanted to do. But the question was, in what area? I was an historian by training and interest, so I enrolled in the Ph.D. program in history at the University of Chicago and began working toward that degree.”

Goldsmith, the Henry L. Shattuck Professor of Law at Harvard Law School, described Sylvester as “super smart and imaginative.”

“I met him when he was a Bigelow fellow when I ran the program,” Goldsmith said. “He was a very intelligent, very funny guy, who knew a lot more about the history of international law, my field, than I did.

“Doug is a rare combination: someone with genuine scholarly bona fides who is also outstanding at administration. He also understands the business of law schools - the fiscal and intellectual challenges posed by changes in technology and in the demand for legal services. And he has good ideas about how to meet these challenges.”

However, like many choices in Sylvester’s life, the Ph.D. and teaching were not going to come easy.

“In 1999, I went on the law teaching market and, frankly, struck out,” Sylvester said. “Legal history, a lack of law firm experience, and a J.D. from an unfamiliar (to hiring committees) law school doomed my chances. I received callbacks from almost every school with which I interviewed at the American Association of Law Schools annual conference, but I interviewed with very few. In the end, faculties, I think, just didn’t know what to make of me. I didn’t fit the mold of a ‘can’t miss’ academic and I wasn’t an experienced attorney.

“So, I went back to the drawing board. I dropped out of the Ph.D. program and joined the firm of Baker & McKenzie in Chicago.”

At Baker & McKenzie, Sylvester worked mostly with start-up dot-com companies, developing his expertise in technology and intellectual property law.

“I loved working with small clients,” he said. “It was really like teaching. My clients needed me to convey a wealth of information about legal risks and opportunities and I needed to find a way to make that information understandable and accessible. I really did see myself doing that kind of work for a long time.”

But, like so much in life, things didn’t turn out exactly as he planned. The dot-com crash of 2001 and then the events of 9/11 forced another U-turn in his career.

“My last six months at B&M, I billed, absolutely zero hours to clients,” he said. “I just didn’t have any left. As a result, I decided to go back on the teaching market and, luckily, found a more receptive audience.”

Sylvester started looking for a teaching position, and was about to accept one, when ASU Professor Cathy O’Grady called to see if he was still looking.

“I told her I could visit if it was in the next two days and if they decided whether to make me an offer within two days after that.”

He flew into town and gave a talk.

“I loved my interview at ASU. It was, easily, the most enjoyable I had. The interactions with the faculty, their keen questions and directions on my scholarship, told me that this was the place for me.”

Sylvester flew back to the Chicago and, a few days later, the phone rang.

“It was Dean Patricia White calling to make me an offer to join the faculty,” he said. “I was absolutely thrilled and accepted on the spot. What was fortunate was that, while I was on the phone with Dean White, I heard a knock on my door. It was the senior partner of the group coming to tell me that I was being laid off due to lack of work. I think he was shocked how well I took it.”

Sylvester has never looked back.

“I love this law school,” he said. “It supported my career, nurtured me. I want to give back and, as a faculty member and associate dean, I have tried. Being dean provides even more opportunity.”

And when the deanship opened, he decided to step forward.

“I was a reluctant candidate,” Sylvester said. “But I’m not a reluctant dean. This is a law school with tremendous upside. It is a place that is already extraordinarily good. What we need to do is to get people to recognize the amazing progress we have made over the past decade or so. I think my job as Dean is to make that happen, and I can’t wait to see where we can go from here.”

In Sylvester’s time at the helm, the law school’s ranking jump to No. 26 overall in the country and No. 8 among all public law schools. It also enjoyed its best fundraising year ever in 2011-12, and has admitted the two best-credentialed classes in its history.

“The community and alumni support has been wonderful,” Sylvester said. “We need to do a lot more to connect to our alums but we are really making progress.

“We’ve visited nearly 100 law firms in town over the past year and I’ve attended more than 200 external events in the past year alone. I enjoy fundraising. I like talking about the law school, hearing from someone about an issue that upsets them and figuring out how to fix it. There are some things we don’t do well, but there’s a heck of a lot we do well and we want people to know it.”

Sylvester, for once, might just be in the right place at the right time.

In law school, Sylvester was in his element, Anna said. Working for the judge in Miami broadened his legal horizons, and at the University of Chicago, things really clicked.

“He decided he wanted to be the person in higher education, teaching really bright students, surrounded by intelligence, research, faculty who would push him to be better and help him grow and develop himself,” she said. “He began to think he could hold his own, and once you realize what you’re capable of, you aim higher.

“If you look back on his life, you might see him as an underdog,” Anna said. “He overcame some odds, often self-inflicted, so he can appreciate those who have also struggled.”

The College of Law might be seen the same way, another diamond in the rough, struggling for years for the recognition it truly deserved, she said.

After coming to ASU, Sylvester would talk with his colleagues about all kinds of grand ideas for the College of Law, some of which happened, some of which haven’t yet, Anna said. So when he got the chance to lead, he stepped forward.

“He wanted to make the good stuff come true,” she said.

Sylvester looks at his life philosophically.

“I may not have always known where I was going and, even when I thought I did, I may not always have ended up where I thought I would,” he said. “But I couldn’t be happier about where I am and more confident that this is where I am meant to be.”

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