When he was 4 years old, Simon Gourdine decided he wanted to be a lawyer.

Born in Jersey City, N.J., and raised in New York City on the Upper West Side and the Bronx, Gourdine ultimately achieved that dream, forging a legal career that took him to South Vietnam and then back to the United States, where he became the highest-ranking African-American executive in pro sports before moving on to become a distinguished public servant.

Gourdine died this month at 72 in a hospital in Englewood, N.J., shortly after having back surgery. And while he never worked in private practice, he was well-known to several lawyers with Am Law 200 firms, who, along with friends and family members, spoke to The Am Law Daily last week about his life and work.

Whether via the sports or civic arenas, those who knew Gourdine remember him as a soft-spoken and thoughtful man who earned the respect of his colleagues while serving as a trailblazer for a younger generation of African-American lawyers.

“My father would certainly have been proud to be called a pioneer,” says Peter Gourdine, a commercial litigation associate at Day Pitney in Parsippany, N.J., who left a job with the National Basketball Association’s broadcasting division to attend law school at the age of 31 at his father’s urging. “He always said getting a legal degree provided him with a variety of options, and he encouraged me to do the same.”

Simon Gourdine’s own ties to the NBA ran deep. His wife Patricia, a retired New York City public school teacher, recalls that his first day with the league was June 3, 1970. She remembers the date because it fell just two weeks after the birth of their first child, David.

Gourdine had been hired as a legal assistant to then – NBA commissioner Walter Kennedy, a former mayor of Stamford, Conn., says Pat Gourdine. A mutual friend had recommended Gourdine to Kennedy during the former’s brief stint in the U.S. attorney’s office in Manhattan under Robert Morgenthau.

For Gourdine, the ensuing 12 years with the NBA were among the “most rewarding he had professionally,” his wife says. He was elected as the league’s first-ever deputy commissioner in 1974 — a post now held by former Cravath, Swaine & Moore litigation associate Adam Silver — as a result of his ability to disagree with Kennedy and provide sage legal counsel in crafting a free agency system for players, according to a story at the time by The New York Times. (That system remains mostly intact today.)

When Kennedy retired in 1975 and was replaced by former Democratic National Committee chairman Larry O’Brien, Gourdine continued to play a key role for the league, advising on a landmark antitrust suit filed by the rival American Basketball Association and negotiating the finer points of a 1976 merger between the two leagues. Gourdine also handled the 1977 labor negotiations with league officials that led to a strike and brokered a settlement that same year allowing the Nets franchise to move from Long Island to New Jersey. (As it happens, the Nets are headed to Brooklyn this fall.)

“Sy was an enormously impressive and elegant man with an unerring sense of right and wrong,” says Skadden, Arps, Slate, Meagher & Flom antitrust and litigation partner Jeffrey Mishkin, who served as the NBA’s chief legal officer from 1992 until 2000. Mishkin, who began his legal career at Proskauer Rose in 1973, first met Gourdine that year in connection with that firm’s work on behalf of the league.

As outside counsel to the NBA, Mishkin worked closely with another young Proskauer lawyer named David Stern, who left the firm in 1978 to become the NBA’s general counsel. Stern also worked closely with Gourdine, who took a 14-week leave of absence from the league in 1979 to attend an advanced management program at Harvard in preparation for upcoming collective bargaining talks with players. In his 1992 book Elevating the Game: Black Men and Basketball, author Nelson George wrote that many in NBA circles “spoke optimistically about Gourdine one day becoming commissioner.”

It didn’t happen. Gourdine retired from the NBA at 40 in 1981 when it became apparent to him that he would not succeed O’Brien as commissioner. Stern took over the job on Feb. 1, 1984, and has held it ever since.

“Simon Gourdine made an extraordinary impact on the [NBA] over his nearly 20 years of service with our league,” Stern said in a statement issued in the wake of Gourdine’s death. “The NBA family has lost an innovator and a great friend.”

Peter Gourdine says that despite his father’s disappointment at not getting the commissioner’s job, he never dwelled on what might have been: “My dad was always guided by doing what he thought was right for all the parties involved.”

Gourdine returned to professional basketball almost a decade later, but only after holding several other important public sector jobs. He sandwiched a two-year stint in the mid-1980s as corporate secretary for the Rockefeller Foundation between serving as commissioner of consumer affairs under former New York City Mayor Edward Koch and labor relations director for the Metropolitan Transportation Authority.

“Sy was a very good friend who performed an unbelievable service to the city,” says Koch, now a partner at Bryan Cave in New York. “I knew his reputation at the NBA was sterling, but he was so dedicated to serving New York in many different capacities, and he also was once a candidate to become police commissioner.”

Pat Gourdine notes that her husband grew up in the same Upper West Side neighborhood as current police commissioner Ray Kelly. In later years, Gourdine served as deputy commissioner of trials for the New York Police Department between 2002 and 2006. Peter Gourdine notes that a full NYPD honor guard was on hand for Gourdine’s funeral last week in the Riverdale section of the Bronx, his home for nearly 40 years.

Among those attending the service was Frederick “Fritz” Schwarz Jr., senior litigation counsel at Cravath. Schwarz says he got to know Gourdine well during his time as corporation counsel for the city of New York in the mid-1980s, when the two lawyers would frequently meet for lunch at a Thai restaurant north of the courthouses in downtown Manhattan. When Schwarz was named chairman of a charter revision commission tasked with proposing reforms for the New York City government in 1989, he looked to Gourdine to assist him.

Schwarz recalls the period as being a difficult one for race relations in the city and says he felt that at least six of the panel’s 15 members should come from minority backgrounds. That led Schwarz to enthusiastically endorse Gourdine as a candidate for inclusion on the commission. Schwarz says that Gourdine pushed hard on “equality issues” and for holding all commission discussions in public — something Schwarz believes eventually “condensed the warring factions in getting recommendations passed that fundamentally changed” the way New York City is governed.

After the charter panel finished its work, Gourdine returned to the NBA in 1990, this time as general counsel of the league’s players union. In past interviews with The Times and Sports Illustrated, Gourdine, a founding member of The National Conference for Black Lawyers, said his working class upbringing helped endear him to many NBA players, the overwhelming majority of whom were black.

Gourdine took over as executive director of the National Basketball Players Association in April 1995 upon the resignation of Charles Grantham and an intense round of collective bargaining talks with the league, which was threatening a lockout. It was a contentious time, with some players expressing skepticism about Gourdine’s allegiance to the union cause given his previous history in the league office.

Schwarz, who now serves as chief counsel of the Brennan Center for Justice at New York University School of Law, says that before assuming the executive director role, Gourdine called him for suggestions about whom to hire as outside counsel for an antitrust fight against the NBA. “I gave him the names of a few firms, and at the end I said, ‘I’d certainly like a shot at it,’” Schwarz says. “And so he hired me.”

The case went before U.S. District Judge Kevin Duffy in Manhattan, whom Schwarz says was initially tough on the league and its lawyers from Skadden and Proskauer. Unfortunately for Schwarz, Gourdine, and the players, Duffy eventually dismissed the union’s suit in 1994.

Gourdine and the NBPA subsequently agreed to a tentative $5 billion collective bargaining deal with the league in August 1995. But a Michael Jordan – led group of star players, backed by their high-profile agents, opposed the pact and ultimately succeeded in scuttling it and forcing out Gourdine in 1996. (Gourdine prevailed in an arbitration proceeding against the NBPA in 1997 when a three-member panel awarded him his remaining $883,738 in salary, plus interest.)

Schwarz says the dissident group was represented by former Weil, Gotshal & Manges partner Jeffrey Kessler, who went on to head the sports litigation practice at Dewey & LeBoeuf before leaving the now-defunct firm in May for Winston & Strawn, which is now primary outside counsel to the NBPA.

Kessler, who did not respond to a request for comment, and super agents Marc Fleisher and David Falk helped usher in a new regime at the NBPA headed by current executive director G. William Hunter. Hunter led players through their recent collective bargaining crisis before coming under fire himself earlier this year over his stewardship of the union.

After leaving pro basketball for the second time, Gourdine became general counsel for the New York City Board of Education under former Chancellor Rudy Crew, and served from 2006 to 2008 as chairman of the city’s Civil Service Commission. One job that Gourdine never pursued: working at a large firm.

“He never discouraged me from doing it, but I just think it wasn’t for him,” says Peter Gourdine, who worked at Stroock & Stroock & Lavan before joining Day Pitney. “My dad had a varied career, and the funny thing was he never kept anything on the walls of his office. He always said, ‘You come in the same way you leave.’ He never wanted to be too comfortable.”

Having grown up boxing in the Police Athletic League, Gourdine was a longtime supporter of that organization as well as such other groups as the NAACP Legal Defense Fund. A lifelong Democrat, he considered Barack Obama’s election as president in 2008 a crowning achievement for African-Americans, says Pat Gourdine.

Gourdine himself was a member of the ROTC at City College in the early 1960s, but received a deferment from active service after enrolling in Fordham University School of Law in 1965, his wife says. Three years later, he was shipped off to South Vietnam, where he served as a captain in the U.S. Army investigating matters related to troops stationed in the Mekong Delta.

“On his way [to Vietnam], he was on a ship for 16 days from the U.S. to Okinawa,” Pat Gourdine says. “And he always said that was the reason why we never went on a cruise! I didn’t mind.”

In addition to his wife, to whom he was married for 48 years, Gourdine is survived by his sons Peter and David, a social and mental health worker who volunteers as a team leader for New York Cares, and daughter Laura, a professional actress who also works as a paralegal with the early case assessment bureau at the New York County District Attorney’s Office.

Laura Gourdine told The Riverdale Press that the trajectory of her father’s career surprised some powerful figures at an early stage. Upon being elected deputy commissioner of the NBA in 1974, his secretary buzzed him and said he had a phone call from the president.

” ‘Of what company?’ ” Gourdine asked, according to his daughter. ” ‘Of the United States,’ ” came the reply. Indeed, it was President Gerald Ford, calling to congratulate Gourdine on his promotion.

Brian Baxter writes for The Am Law Daily, a Daily Report affiliate.