Each morning, Sir Laurence Street drives his daughter Jessie to her classes at the Ascham School in Edgecliff. It was “wonderful” becoming a father again so late in life, says the quietly spoken, twice-married 82-year-old former NSW chief justice.

Naturally, there are days when he feels the 66 years separating him from 16-year-old Jessie. But any barriers are physical, “the lack of the agility of the parents of Jessie’s contemporaries".

“I can’t stand on the side of a hockey field for an hour, for example.”

Sir Laurence has suffered a stoop courtesy a bad back these past three or four years; it’s a legacy of an old passion, the 50 to 60 horses he once trained, bending over awkwardly like a shearer to work on 200 or more feet every six weeks.

He sold the last of his horses in 1990, the year he married Penny, his second wife.

He’s bought a book on Pilates and jokes he intends to learn its techniques by osmosis to fix his back; he’s simply been too busy for leisurely reading given his commercial mediation business has kept him busy since retiring from the bench two decades ago.

Sitting now in his chambers on the 12th floor of a Macquarie Street building overlooking the Domain, he’s dressed in a sober grey suit with purple tie, and while the spots on his face show his age, the gleam in his eyes suggest a young and sharp spirit.

“I try not to think about age,” he says.

“In fact, I don’t recognise it. I think we all have a certain amount of Peter Pan in us, really. I can still see myself sitting at the desk at sixth form in school.

“We may lose some of our idealisms as we go on through life, but I’ve been lucky to be able to do things that have provided intense intellectual and emotional fulfilment.”

His latter day work has included trying to sort out leadership conflict at the University of New England – to date too messy to resolve – and travelling to Palm Island, where he reviewed the Queensland Director of Public Prosecutions’ controversial decision not to pursue charges against a police officer over the 2004 death of Mulrunji, an Aboriginal man who sustained severe injuries in custody.

Street found there was enough evidence to send Senior Sergeant Chris Hurley to court, but the officer was cleared of the death last June. Sir Laurence recently bought Chloe Hooper’s book on the case, The Tall Man, but has so far only managed to skim its contents.

Quality time with his teenage daughter is likewise limited; chiefly, says her father, it’s on the 20-minute drive to school, when she’s normally finishing homework. “It’s silly to say I don’t feel a generation gap, because it sounds arrogant – I’m sure Jessie sees a gap – but I never feel any constraints in understanding where she’s coming from,” he says.

Sir Laurence had been present when Penny delivered Jessie in 1992, but this had not been the case with his older children; being in the delivery room wasn’t the done thing for 1950s fathers.

He remembers, for instance, sitting in his chambers preparing an opinion when he received a call to inform him that his first child, Sylvia, had been born.

Jessie hopes to go into law, like three of Sir Laurence’s four grown children from his first marriage to Susan Rankin: Sylvia, now a federal magistrate; youngest son Alexander, a QC; and second daughter Sarah, an employment consultant who trained as a solicitor. Eldest son Ken bucked the trend and became a business consultant.

Sir Laurence insists he has not pressured any of his children to follow him into the law; he has only encouraged them to have ambition and to avoid aimlessness. “It’s very different from my own parents, with whom there was always a huge generation gap,” he says. “Ultimately, you would do as you were told.”

For more than a millennium, the Streets’ history was monopolised by men, given the family has been producing judges since seventh century England.

In Australia, the Streets produced three chief justices of NSW in three successive generations – a record unmatched by any other legal family. Sir Laurence’s grandfather, Philip Whistler Street, was appointed to the top job in 1925; his eldest son Kenneth was appointed in 1950.

Kenneth’s son Laurence, born in 1926, was appointed in 1974, making him the state’s youngest chief justice at age 47.

Yet history forms an equally strong – and certainly more colourful – recollection of Sir Laurence’s late mother, the radical Jessie Street, for whom his daughter is named.

Until about age 40, Jessie Street had been chiefly known as the dutiful mother of four children. But her radicalism and sense of social justice grew through the 1930s Depression.

Her 1938 grand tour of Europe took in the USSR, and she decided socialism might be a solution. Red Jessie, as she came to be nicknamed, controversially forged a Cold War friendship with the Soviet Union, to the condemnation of many political and establishment leaders at home.

In 1943, she stood for Labor in the safe conservative seat of Wentworth, winning the primary but losing on preferences. Sydney – and Australia – might well have become a different place.

Incredibly, her husband’s career still flourished in the deeply conservative political climate. Kenneth Street was appointed NSW chief justice in 1950, the same year his wife took herself off into exile for six years, mostly in London.

Jessie was then free to “pursue her international political agenda”, says Sir Laurence – although his mother was monitored by ASIO and was the target of unsuccessful Menzies Government attempts to revoke her passport; perhaps baiting matters by her attendance at Stalin’s 1954 funeral.

She advocated equal women’s rights, and petitioned for citizenship for Aboriginal people in 1957, a full decade before the 1967 referendum. “People used to say, ‘why are you doing all this?” recalls Sir Laurence. “She would say, ‘I want to make the world a better place for my grandchildren.’”

What impact did the headlines and cartoons satirising his mother have on his father? “Oh, I think they used to distress him. But in those days you didn’t display your emotions; it was the stiff upper lip.” Sir Laurence says he sees himself quite differently from his father, who was emotionally “remote”.

Did he ever disagree with his father politically? “You didn’t have disagreements with your parents in those days,” he says. “It was a much more disciplined period; the children and the parents kept to themselves.”

The retired conservative NSW Supreme Court judge Roderick Meagher – prone to more than a little purple prose about fellow members of the judiciary – told the ABC’s Dynasties program in 2004 that Kenneth “acquired a mistress” during Jessie’s exile.

Is that true? “I don’t know where Roddy got that one from,” says Sir Laurence. “Certainly not to my knowledge. I mean, he had a wide circle of friends; he was a very gregarious man. I’ve been meaning to ask Roddy where he got that from.” Jessie eventually returned home to Kenneth, and the marriage survived.

Perhaps Sir Roddy was closer to the mark when he said of Sir Laurence: “He was his father’s son in that he acted with dignity and appropriateness. He was not his father’s son in that he wasn’t as self-consciously proper as his father.” Sir Laurence’s wife, Penny, has said her husband has a lot more of his mother in him than his father.

“I’ve always enjoyed a streak of irresponsibility, both in my values and in my lifestyle,” says Sir Laurence. “I’ve never felt constrained in my private life by the cast-iron requirements of society. I got divorced, I remarried, and had a second family of one. I have led a life that has not necessarily always conformed to the strict Victorian standards.”

He characterises his politics as occupying the “middle ground”, and believes people are “by and large made what they are by society”; particularly by social inequality.

He shares his late mother’s views on Aboriginal equality; there is a “tragic social climate” on Palm Island, he says. “It’s a beautiful island, but no industry, no agriculture for the unfortunate Aborigines that live there. The only occupation is recreational fishing.

“People on their pension were going down to pick up a slab of beer; it was a soulless and aimless place. The people there are beautiful; the Aboriginal children, they’re just like children anywhere else. But you wonder what they’ve got to live for.”

He remembers signing a “sorry book” to indigenous people at the Sydney Museum several years ago. “I’ve forgotten what I wrote in it, actually,” he says.

“I think we’ve tended to treat the Aborigines without adequate recognition of their equality as human beings. We debased them, particularly with alcohol, and without any opportunity for gainful employment and promotion to significant places in our society.”

What about Labor’s plans to withhold welfare payments to families whose children fail to attend school? “The stick is not the right approach to use anywhere, I believe.”

Nonetheless, Sir Laurence has never felt compelled to enter politics. He reveals to Extra he was once offered a safe seat. Which party? He pauses and raises his eyes to the ceiling in thought: “I think I can say, because everybody’s dead now.” In the early 1960s, he says, the Liberal Party offered him the safe seat of Parramatta, which Sir Garfield Barwick was vacating to become chief justice of the High Court.

The seat eventually went to Nigel Bowen in 1964, who held it until 1973 and served as attorney-general.

“My ambition was the bench, not politics,” says Sir Laurence. “I hate arguments and have an absolute hatred of violence in any form, including verbal violence and hurling abuse across the chamber.”

He picks up a book he has penned on mediation – a field he pioneered in Australia – and points to “characteristics of mediators”: they must have “the humility to be non-judgemental”, he writes, and be ready to “empathise” with different points of view.

Sir Laurence is not one for drinking down the club, and prefers mixing socially across age groups, “getting involved with people’s emotional textures”. Basically, he concedes, “I’m not a man’s man.” Party politics never stood a chance.