Pictured, from left, are Judges Walter K. Stapleton and Brett Kavanaugh. Pictured, from left, are Judges Walter K. Stapleton and Brett Kavanaugh.

Long before his nomination to serve as an associate justice on the U.S. Supreme Court, Brett Kavanaugh got his start clerking for Walter K. Stapleton, the influential federal judge who has served as a mentor to some of the most prominent figures in Delaware’s legal community.

Kavanaugh’s work for Stapleton in 1990 came before a clerkship on the U.S. Court of Appeals for the Ninth Circuit and, eventually, a stint with U.S. Supreme Court Justice Anthony M. Kennedy, the man he now hopes to replace.

But his time in Delaware also earned Kavanaugh a coveted spot among former Stapleton clerks who have since ascended to state and federal judgeships. Stapleton, 84, served as a commissioned judge on the U.S. Court of Appeals for the Third Circuit from 1985 to 1999, and has thereafter held senior status on that Philadelphia-based court. He first joined the federal bench at the age of 36 and is widely regarded in Delaware as a legal icon with a knack for cultivating talent across the ideological spectrum.

Of the nearly 100 law clerks to serve in Stapleton’s chambers, four have become judges themselves, including Delaware Supreme Court Chief Justice Leo E. Strine Jr. and Leonard P. Stark, the chief judge of the Delaware district court. William T. Allen, former chancellor of the Delaware Court of Chancery, clerked for Stapleton between 1972 and 1974.

Colm Connolly, a Republican who is nominated to serve on the district court, would be the fifth judge to emerge from a Stapleton clerkship, if confirmed by the U.S. Senate.

“Quite apart from the numbers … those are very formidable people,” said Lawrence Hamermesh, professor of corporate and business law at Widener University Delaware Law School.

Appointed by two Republican presidents, Stapleton is regarded much less for his ideological leanings than his hard work and attention to detail on the bench. And among his clerks, Stapleton was known for his friendly disposition and outgoing nature.

“The one thing I know about Walt Stapleton is that he is not an ideologue,” Hamermesh said. “The one thing I’d characterize Stapleton as is workmanlike, and I think that rubbed off.”

As an active member of the court, Stapleton had a habit of taking his clerks out to lunch, and would often walk with them down to the Brandywine River on warm summer days.

It was during those excursions in Wilmington that Timothy Jay Houseal, now a partner with Young Conaway Stargatt & Taylor, said he first ran into Kavanaugh. The two have since remained in contact, occasionally collaborating on Supreme Court briefs or interacting through Kavanaugh’s later work at the White House.

Houseal, a young attorney at Young Conaway in 1990, said Kavanaugh showed an interest in litigation and appellate advocacy, and he remembered Kavanaugh as a hard-working lawyer with a drive to secure to be a judge. At the time, Houseal said, a Supreme Court clerkship was far more appealing to Kavanaugh than a spot at one of Delaware’s high-power commercial firms.

“He’s a very serious guy, but very warm,” Houseal said. “In a lot of ways, he reminds me of Judge Stapleton. As a law clerk, he was destined to be a judge.”

Kavanaugh, 53, is perhaps the most conservative jurist to clerk under Stapleton. After working in private practice at Kirkland & Ellis in the late 1990s, he spent three years as associate counsel in Kenneth W. Starr’s independent counsel investigation of President Bill Clinton. He served five years in the Bush administration as staff secretary and assistant to the president, before his confirmation to the D.C Circuit in 2006.

During his time on the court, Kavanaugh has built a reputation as a conservative stalwart, wary of the power of federal agencies and penning opinions in support of broader gun rights.

President Donald Trump on Monday nominated Kavanaugh to fill the seat of Kennedy, who announced his retirement from the Supreme Court in late June.

Kavanaugh worked for Stapleton after his 1990 graduation from Yale Law School. After his service for Kennedy, he worked in the George W. Bush administration. Bush appointed him to the U.S. Court of Appeals for the District of Columbia Circuit.

A native of Cuthbert, Georgia, Stapleton moved with his family to Delaware at the age of 4 and attended Wilmington Friends School. He earned his undergraduate degree from Princeton University and holds law degrees from Harvard Law School and the University of Virginia. In 1959, he joined Morris, Nichols, Arsht & Tunnell, where he worked closely with partner S. Samuel Arsht.

In 1970, President Richard M. Nixon appointed Stapleton to the Delaware district court, where he served as chief judge from 1983 to 1985. Nominated by President Ronald Reagan in 1985, he served 14 years on the Third Circuit before assuming senior status in June 1999.