Benchmark of the Delaware Supreme Court

Almost 20 years ago, this magazine named Leo E. Strine Jr. one of 49 “People to Watch in 1996.” For years, that “honor” was a running family joke. For instance, Strine says, “Whenever my wife and I got a good table at a restaurant, I would say, ‘See, that’s because I’m a person to watch.’” Joking aside, the prediction was prescient. In ’95, Strine, then 31, was counsel to first-term Gov. Tom Carper. Today, he is chief justice of the Delaware Supreme Court, the latest stop in a career marked by singular professional and personal achievements—along with no small amount of controversy.

Growing up in Hockessin, Strine’s thoughts focused more on soccer than a career in law. With his younger brother Michael, he spent countless hours kicking a ball into the goal his father had constructed in the backyard of their Meeting House Meadow home. All that practice paid off: He was named to the All-State team as a senior at Alexis I. duPont High School.

Today, Strine, whose humor is often self-deprecating, likes to say his dream that one day the world’s best soccer player would be 5 feet 7 inches and named Leo has come true—sort of: Arguably, the best player in the world is Lionel Andrés “Leo” Messi, an Argentine who, like Strine, stands 5 feet 7 inches.

His parents, Leo Sr. and Peggy, still live in that Meeting House Meadow home. In their early 70s and very active, they have lived a classic American love story. Both grew up in separate, working-class, row-home neighborhoods in Baltimore. Leo Sr. went to an all-boys Catholic school, Peggy to an all-girls Catholic school, and they met at—where else?—a CYO (Catholic Youth Organization) dance. They married when Leo Sr. was 19 and Peggy was 18.

In 1973, when Leo Jr. was 9 and Michael was 7, the senior Strine took a job with Lit Brothers department store in Philadelphia. Casting about for nearby affordable housing in a good school district, the family settled in the growing community of Hockessin. The Strine boys went to the old Yorklyn Elementary School, then to H.B. duPont Middle School and finally to A.I. 

Both boys enjoyed sports. Leo played basketball, Little League baseball and rocked long blond hair (in contrast to his current horseshoe hairline) as quarterback on a Pee Wee team. A shoulder injury ended his football career when he was 10, and soccer became a passion. Leo Sr. knew little about the sport until his sons took it up, but he learned enough to become A.I.’s head coach in Leo Jr.’s senior year.

The parents fashioned family vacations into lessons in history and civics. Eschewing the nearby beaches, they traveled to historic sites throughout the East and Southeast: Gettysburg, Washington, D.C., Williamsburg, Antietam, West Point, FDR’s home in Hyde Park, N.Y. The chief justice, an avid reader throughout his life, remembers that two of his first books were “Meet Abraham Lincoln” and “Meet Martin Luther King Jr.”

“We were raised with the idea that we should make something of ourselves,” Strine says. And there was never any doubt that, unlike their parents, Leo and Michael would go to college.

First, though, Strine had to get through an out-of-character period in high school when, he claims, his grades “were appalling.” An indifferent student in math and sciences, he found himself in danger of being ineligible to play soccer, which served as a wake-up call. “That’s when I decided to concentrate on the books. I had a difficult time with balance back then, and I will always wish I had been better at getting my act together.”

Whatever difficulties he encountered were outnumbered by bright spots during his years at A.I. It was there he met his future wife, Carrie Rainey, a standout field-hockey player who went on to play at Ursinus College in Pennsylvania. Strine’s All-State honors plus a high score on the SAT attracted attention from a few colleges, but he ultimately chose the University of Delaware. He had planned to play soccer there, but after trying spring ball his freshman year, he decided it would take too much time from his studies. That worked out well: He won the Harry S. Truman Scholarship, was named to the Panel of Distinguished Seniors of the College of Arts and Science, was inducted into Phi Beta Kappa and was named the outstanding graduate in political science.

Also at UD, he got his first taste of Democratic Party politics. As a freshman in 1982, he volunteered for Carper’s successful campaign to unseat Republican Thomas B. Evans Jr. for Delaware’s lone seat in the House of Representatives. In ’84 he again helped Carper and also volunteered in Sen. Joe Biden’s re-election effort. He became expert at blowing up balloons and, he says, “I can still do a political polling phone call pretty much from memory.”

More important was the effect politics had on his personality. “I was very shy, and campaigning got me over that,” he says, adding that when he and his future wife took the Myers-Briggs personality test during Pre-Cana consultation prior to being married in the Catholic Church, they came out on opposite ends of the scale, he as an introvert and she as an extrovert.

Strine graduated summa cum laude, then enrolled in the University of Pennsylvania Law School. Still in thrall of Delaware’s new congressman, he used a borrowed car to travel from his small Philadelphia apartment back home to run Carper’s volunteer corps and help him get elected again in 1986. He also found time to graduate magna cum laude and wed Carrie, who was in graduate school at Thomas Jefferson University.

Strine went on to serve two clerkships—one with Judge Walter K. Stapleton of the U.S. Court of Appeals for the Third Circuit and another with Chief Judge John F. Gerry of the U.S. District Court for the District of New Jersey. Next, he joined Skadden, Arps, Slate, Meagher & Flom, one of the largest and most prestigious law firms in the country, as a corporate litigator in the Wilmington office.

Carper was elected governor in ’92, and immediately appointed Strine as his counsel—a post the chief justice today calls “the most fulfilling job of my career.” He was not only the governor’s lawyer but also his policy coordinator, and those policies obviously lit a fire in the young liberal’s belly. Strine told one interviewer: “I had a boss who was fighting the good fight on every front. How many people get to say that they were one of the leading drafters of a statewide welfare reform act that was critical in the shaping of the national debate, that they wrote a state charter-school law, state ethics reform? It was an intellectual feast.”

He also cites Carper’s support of gay rights. In 1997, the governor signed an extension of the hate crime bill to include instances in which a person is victimized simply because of his or her sexual orientation. Obviously impressed with his boss’s courage, Strine says, “He was so strong in supporting gay rights that there were some people who thought he was gay.”

While Strine claims to have “enjoyed working with the legislature,” the feeling was not always mutual. His youth, aggressiveness and sometimes biting wit (this magazine called him “droll”) ruffled a few legislative feathers. “He wasn’t a schmoozer,” says Michael Kelly, a fourth-generation Delawarean and Wilmington lawyer who’s well connected politically. “He was a no-nonsense representative of the governor—bulldog tough. He would take legislators head-on. But he loves Delaware, and he took a pay cut (leaving Skadden, Arps) to work in the government.”

In 1998, his judicial career began. Carper nominated him for the Court of Chancery, the crown jewel of the state’s court system and the primary reason for Delaware’s national pre-eminence in the field of corporate law. Thanks to his sometimes contentious dealings with legislators and his young age (34), Strine was a tough sell, but his nomination was finally approved by a slim majority of the 21-member Senate, 12-9. A few days later, Carrie Strine, an occupational therapist at Alfred I. duPont Hospital for Children, gave birth to their first son, James. (Two years later, they had a second son, Benjamin. They attend Salesianum School.)

Strine took to his new post like someone born to wield a gavel and wear a black robe. He soon became a kind of rock star of the bench, thanks to colorful opinions spiced with music and pop culture references as disparate as Snooki of TV’s Jersey Shore, novelist John Cheever and Ralph Lauren’s original surname (Lifshitz). His bon mots can sometimes have an edge to them, and the legal publisher Lawdragon.com once likened his appetite for “skewering fat cats” to the way “Hannibal Lecter loves fava beans and a nice Chianti.” Strine also has shown a tendency to address subjects not directly related to the issue before him.

Bon mots and meanderings aside, many of his opinions are considered brilliant and among the most influential rulings in corporate law.

Samuel Hoff, George Washington Distinguished Professor of History and Political Science and law studies director at Delaware State University, has described Strine as “a legal wunderkind,” an appellation that seems appropriate. Strine has published dozens of papers in many law reviews, spoken to groups both inside and outside the legal profession, and teaches at Penn Law School in the spring and Harvard Law School in the fall.

In 2011, he was named chancellor of Chancery Court, and in January of last year, Gov. Jack Markell nominated him to succeed Myron Steele as Delaware’s eighth Supreme Court chief justice. He was confirmed—this time unanimously—on Feb. 28, 2014. Since then, Strine has welcomed three new justices to the court, formed a committee to overhaul problem-solving courts and started a commission for access to justice.

But while his career has earned him extensive praise for both legal acumen and wit, he’s come in for a fair amount of criticism. The most serious was a rebuke from the Delaware Supreme Court in November 2012 for what the court said was an improper digression in a Chancery Court opinion. Strine’s decision on a contractual dispute went on for 11 pages about an issue related to limited liability companies.

“[Strine’s] excursus on this issue strayed beyond the proper purview and function of a judicial opinion,” the Supreme Court wrote, adding, “We remind Delaware judges that the obligation to write judicial opinions on the issues presented is not a license to use those opinions as a platform from which to propagate their individual world views on issues not presented.”

Strine asserts, rather forcefully, that he was later vindicated. Lawrence A. Hamermesh, a professor of corporate law at Widener University Law School, agrees: “There was a statutory change that essentially enacted the view of the law that Chancellor Strine articulated. In his view, the issue was something the parties had raised, and he had to decide, and the legislature subsequently adopted the Strine view of the law.”

In an email, Hoff adds: “Chief Justice Strine’s defenders will most likely say that the 2012 rebuke was an unfair punishment for his enthusiasm and willingness to challenge convention.” Challenging convention has been a trademark of Strine’s short tenure as the state’s highest ranking jurist. His opinions—in and out of court—have sparked plenty of controversy. In January, in a speech at a Martin Luther King Jr. breakfast, he said that Delaware “can’t incarcerate our way to public safety,” and noted “shocking disparities” for blacks in the prison system. Then he added, “You don’t want to be in a state where incarceration rates are associated with North Korea.”

The last remark drew the ire of state Sen. Greg Lavelle, R-Sharpley, who called out Strine on the Senate floor. “Comparing any aspect of the United States to North Korea is just misplaced,” Lavelle says. “I know the point he was trying to make, but you really need to be thoughtful when you make that point, particularly given the position he holds.”

Lavelle notes that Strine, who is in the second year of a 12-year appointment, has an advantage over elected officials like himself. “In the political realm,” says Lavelle, “we have to accept the consequences of our statements, and sometimes it’s not pleasant. But to toss it out there and then retreat back into his chambers, I don’t think that’s a good model on public policymaking.”

Lavelle says the reproof earned him “a lot of high fives in Legislative Hall.” Through a spokesman, Strine responded in January, saying he “had great respect for Senator Lavelle,” but the legislator had taken his comments out of context. He expressed surprise that Lavelle hadn’t contacted him directly with his concerns.

Unlike Lavelle, John Flaherty, president of the Delaware Coalition for Open Government, finds Strine “refreshing.” Says Flaherty, “I like his willingness to use the bully pulpit of his office to weigh in on the tougher issues.”

Criticism hasn’t dampened Strine’s zeal for speaking out. A month after the MLK Jr. breakfast, he told The News Journal that the city, state and New Castle County police forces should merge. The suggestion, which The News Journal said “had been discussed quietly for years,” was quickly rejected by officials in charge of those law enforcement units.

Recently, in his chambers in downtown Wilmington, Strine, sporting his signature suspenders and colorful tie, conducted a quick tour of the framed photographs crowding the office’s credenzas and bookshelves. Some of the photos trace the retreat of his hairline, but his favorites are those showing him as coach of his sons’ teams. 

In a wide-ranging interview, he touched on several subjects, including education and the environment. He suggested that the school year should be extended to 225 days, with classes from 7:30 a.m. to 5:30 p.m. He believes that calendar would benefit all parties: It would provide a safe environment and nutritious meals for students, along with more arts instruction and less homework; reduce after-school concerns for parents (“Who gets off work at 3 in the afternoon?” he asks); and give teachers more leverage in seeking raises.

While such a change may seem radical, he says, “We can’t stay mired in the past and be preeminent. We don’t have the luxury of relearning the lessons of history as slowly as previous generations.” That applies to the environment, too. “We should be leading the environmental movement,” he says, “and we shouldn’t despoil it by creating industry.”

Despite his excursions into non-judicial areas, Strine revels in his duties as chief justice. He notes with some irony that in grad school he hated writing term papers. “Now,” he says, “I write term papers as part of my job.” A lover of words who aims for “clarity of expression” in his opinions, he is given to musing on why people can’t get “affect” and “effect” right, and finds “subsequent to” and “prior to” wholly inferior to “after” and “before.”

Some observers have speculated that Strine’s interest in policy and government may portend a run for public office. He denies such ambition. “For one thing,” he says, “I don’t have the money to conduct a campaign. And I’ve been privileged to serve the people of Delaware since I was 28, and it’s been very gratifying.” But then, after a pause, he adds, “As you get older, and if you’re wise, there are two words you say less often: always and never.”