After nearly five decades in the courtroom trenches, criminal defence lawyer Craig Caldicott has seen it all – from minor traffic offences right through to the most heinous of crimes. “You don’t get that much time for murder,” says Craig, reflecting on his 47-year career.

His job involves working around-the-clock on major cases where a client’s future hangs in the balance, and stepping into jail cells to interview people at the lowest points of their lives. Yet, despite this pressure, Craig maintains an inner calm that seems almost at odds with the intensity of his work.

That same calm greets SALIFE at the door of his Brighton home – a stately 1920s gentleman’s bungalow which he purchased in 1985 and has lived in ever since. The home has recently undergone a stunning transformation with a soaring new extension; a bold vision of Craig and his wife Jill Kirkwood.

Craig and Jill met nine years ago, each with three of their own children, making their blended family “a bit of a Brady Bunch”. At first, friends asked Jill if she was aware that she was dating the “bikie lawyer”, as Craig was famously once labelled by former premier Mike Rann. While members of certain motorcycle groups have been clients over the years, Craig has represented people from all walks of life.

“I always know he’s going to have a busy weekend when he brings a suitcase full of folders through the door on a Friday afternoon,” Jill says. “Craig copes with enormous amounts of stress, I think better than most people. And he’s certainly interesting around a dinner party.”

Craig has lived in his beloved home for 40 years, but the old bungalow was not built for modern living and the couple began dreaming of an upgrade. They loved the character and nostalgia of the home, and so began hunting for a team who could create a bold extension to the home. “Wow us,” was the brief.

The project was designed by Michael Fogarty and constructed by Bellevue Building Concepts. Jill’s son Tom Rossi, the director of Glenelg Electrical, installed the electrical work throughout the home. The interior design was created by The Design Duo’s Alisa and Lysandra Fraser.

Bellevue director Matt Pernini says the design centred on a key request: a wine cellar big enough for Craig and Jill to host guests in. The cellar is the jewel in the crown of the new extension, accessed by an automatic glass door in the floor. But it posed a major engineering challenge that saw a swimming pool-sized hole dug in the centre of the home, deep into soft beach sand.

“We’re lucky to specialise in custom projects, but you don’t get many such as this where a client says, ‘okay, here’s a blank slate, we want you to wow us’,” says Matt. “Big architecturally-designed homes can feel as if they are show homes, but this house very much feels like Craig and Jill’s home.”

The couple lived in the home throughout the project, which took most of two years. Jill worked closely with Alisa and Lysandra on the final touches, with giant imported light fittings and stylish furniture complementing the overall theme.

“I’ve always admired the American farmhouse style, but we wanted it to be more refined and elegant. It is a very collaborative result,” says Jill.

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“We wanted a big kitchen and family room where we could entertain. We do love our wines, and wanted to showcase the cellar. As we fell in love with that idea, we worked everything else around that. The tradespeople all recognised it was something special, and the end result shows a high level of craftsmanship.”

For Craig, the home’s new iteration provides a relaxing and idyllic retreat from the stress of his work, and is helping him stay on top of his game. And yet, despite the luxury abode being about as far away from a Yatala prison cell as you might get, Craig is a battler at heart whose tenacity to fight for the underdog was ingrained through humble beginnings.

He and his two brothers grew up at Brighton, raised by their single mother Shirley. Times were often tight. Craig recalls one particular day, when Shirley had to choose between paying
30 cents for Craig’s school excursion or to buy milk.

“While we lived in a good location, we were basically poor. My mother did everything she could to support us, working long hours at the Adelaide Central Market while effectively raising three boys single-handedly. She was a great mum and loved us dearly,” says Craig.

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“Our mother was a battler who always strove to do the right thing. She was frugal and made a great home for us. It was a struggle but it made me the person I am today.”

Craig went to Brighton Primary School and Brighton High School. He didn’t get the marks he wanted after school so repeated Year 12, while working nights and weekends at pubs, so he could study law. All while spending summers on the beach with Brighton Surf Life Saving Club.

At the end of his first year working for a law firm, Craig was not offered a permanent position, so he got to work by pounding the pavement, handing out business cards and setting up an office in his mum’s kitchen – carving a law practice out of thin air. The humble beginnings of what would one day become a leading South Australian law firm, Craig Caldicott Lawyers.

“We lived on the esplanade; Mum was my receptionist and she would open the door for my clients. We had very interesting clients, all sorts of weird and wonderful people. After 18 months, I moved into an office on Brighton Road. In the early days, it was 12 hours-a-day, seven days-a-week,” says Craig.

“Once, I got on my trusty little motorbike, rode to the family court and got a clerk to help me work out how to fill out the forms for someone’s divorce. I did all of that. But after a while, I decided that family law wasn’t for me.”

Craig gravitated to criminal law. One of his earliest criminal cases was for a client who was charged with stealing the washing from her neighbour’s clothes line. “I was always going to lose that case, but she wanted to plead not guilty and we fought it for three days,” recalls Craig.

“Through word of mouth, people would come to see me and I would represent them and work really hard at it. It was very rewarding because clients were appreciative if you represented them to the best of your ability, and I was good at it,” he says.

Early in his career, Craig worked as a duty solicitor doing pro-bono work, visiting police cells in the early hours of the morning to assist people who couldn’t afford a lawyer. As his reputation grew, he took on some of the state’s most high-profile cases.

Craig acted for the late Domenic Perre in the 56-day-long inquest into the 1994 bombing of Adelaide’s National Crime Authority office. He also represented the late James Miller who died while serving a life sentence for his role in the murder of six women in the 1970s, the so-called Truro murders.

Another public case was that of alleged war criminal Ivan Polyukhovich who was accused and acquitted for involvement in the mass execution of hundreds of Jewish people in Ukraine during World War II. For that case, Craig travelled to Ukraine to gather information to help exonerate his client.

Public vitriol has come Craig’s way at times, particularly so when he represented an Adelaide man who lost control of his Lamborghini which tragically killed a pedestrian in 2019. That case saw the state government introduce new licensing laws for owners of high-powered vehicles. “I have been vilified with hate mail, threats and comments on social media. It has been hard at times, but it comes with the territory,” says Craig.

He explains that defence is a fundamental pillar of the legal system and it’s the prosecution’s job to prove that the accused committed the crime.

“That’s what I stand for. I’m passionate about helping the little guy fight the big guy, namely the state,” he says. “Sure, some people say: ‘how could you represent that person?’ But everyone deserves to have good representation, otherwise the system would fall apart. Some of my most difficult cases have been for people who, deep down, I knew were totally innocent and they stood a grave risk of going to jail for a long period of time.

“There are some innocent people who are in jail, and that’s what I find most troubling. Being charged with any criminal offence can be a terrifying experience. If someone says to me that they’re not guilty, then we fight it. That’s my duty. But if someone says to me: ‘I’m guilty, but I want you to plead not-guilty at trial’, I won’t take their case – it goes against my ethics.”

Craig is the chair of the Criminal Law Society and is often approached for advice by professionals from all corners of the legal system. While Craig could have gone down the path of becoming a judge, sending people to prison goes against his beliefs. In fact, he thinks most prisoners shouldn’t be there.

“There’s a select few in jail who I think are seriously dangerous and should stay there. But the rest, I wouldn’t keep them in. Jail doesn’t work. We need to be fixing the problem at the front end, rather than locking people away,” says Craig.

Craig says most clients see him as their confidant and treat his waiting room as a demilitarised zone. There’s only been one time when Craig has felt palpable fear for his own safety.

“The scariest moment of my career was meeting a man who’d just been arrested for killing three of his neighbours and injuring two police officers, and I was in the cells with him the next morning. He was about six foot four, built like a tank, and with his eyes wide open, he said to me that God had told him to do it. The hairs stood up on the back of my neck,” he recalls.

Craig purposefully didn’t encourage any of his children into law, but his son James Caldicott is following in his footsteps, and now is an up-and-coming defence lawyer.

Craig is a life member of Brighton Surf Life Saving Club, and has for 50 years volunteered as a legal advisor to Surf Life Saving South Australia. In 2023, he was awarded a Medal of the Order of Australia for his services to law and surf lifesaving. To keep fit, he swims 1.5 kilometres along the beach about once a week. And to de-stress, he reads every night.

It’s only when Craig travels to different time zones that he’s truly able to switch off. He’s previously climbed Mount Kilimanjaro, Everest Base Camp and Machu Pichu, each alongside one of his children. “I’m just waiting for Jill to hike Kilimanjaro with me,” says Craig, to which Jill laughs: “that’s not my idea of a holiday”.

Jill says she and Craig do share a love of travel. This year, they plan to visit the Maldives, Canada and Alaska. A previous trip to South America inspired the Argentinian grill in their new outdoor dining pavilion.

“In the time Craig and I have been together, we’ve combined our families and pursued similar interests in travel. We’ve been very fortunate to travel to some amazing destinations with incredible experiences that we will continue to pursue,” says Jill.

“Having a blended family can have its challenges. Everyone has busy lives with their own growing families, but we do tend to try and pull them together as often as we can,” she says.

Now when they go away, there’s nothing like coming home. And although some might question the necessity behind the grand size of their new extension, the couple agree it’s been worth every cent.

Jill explains: “This build has provided us with a really comfortable space to de-stress, whether we’re entertaining or just sitting here in front of the fire. It’s where we spend a lot of time with our family. If we’re blessed enough to have many more years of good health with our family and grandchildren, this is where we want to be.”

While Jill is semi-retired, Craig is not looking to retire any time soon. “People often ask me when I’m going to retire, but then I think, what am I going to do – prune the roses? I feel I’m doing something positive for people. I’m seriously passionate about it. And more importantly, it enables me to fund my holidays,” Craig jokes.

Craig’s new four-metre-long kitchen benchtop is a long way removed from his mum Shirley’s dining room table where he started working for clients nearly 50 years ago, but his drive remains the same.

“I need to work on a personal level. Sometimes I think it’d be nice to turn it back every now and again, just a notch, but as long as I keep enjoying it, that’s the key.”

This article first appeared in the July 2025 issue of SALIFE magazine.