5 minutes with: Craig Wing, Citizen Kanebridge Ambassador

Can you share your background & journey?

Well, I suppose most people remember me from my days playing rugby league for the Roosters, Rabbitohs, and NSW.
I was fortunate enough to become a dual international after moving to Japan to play rugby union, and I thrived under the pressure that came with competing at the highest level of sport.

These days, the game has changed, but the fundamentals of how I apply myself remain the same. I now navigate Sydney’s most exclusive property markets—the CBD, Eastern Suburbs, and Lower North Shore. I work behind the scenes to secure some of the city’s most coveted homes. Given the nature of my client base, my work also extends into commercial property. While the mechanics differ, the same principles of access and discretion apply.

You started investing in property as a teenager. How has your approach evolved?

As a young athlete, I was encouraged to invest early, and property seemed like a safe bet. My first purchase was a terrace in Paddington in the late ’90s when I was 19. I focused on blue-chip assets from the start.

Over time, my portfolio grew, and I experimented with some speculative property investments, which led to tough but invaluable lessons.

Rather than walking away, I refined my approach and developed a deep passion for property. Now, I guide and invest based on first-hand experience, focusing on long-term value to ensure that decisions are grounded in fundamentals rather than fleeting trends.

As someone who has spent years in the media spotlight, how do you ensure discretion for your clients?

I’ve experienced the discomfort of having personal affairs turned into headlines. Many of my clients are high-profile individuals who prioritise discretion just as much as I do.

For me, privacy isn’t just a promise—it’s a discipline. I carefully control the flow of information, work only with trusted professionals, and secure most deals off-market to ensure confidentiality.

Some of the biggest transactions I’ve facilitated have gone entirely unnoticed because that’s how my clients prefer it. While some suggest I should publicise my work more, I build my business on trust and referrals from those who appreciate true discretion.

What do you focus on when helping your clients find the right property?

The first step is understanding why my clients are buying—whether they’re upsizing, downsizing, or investing—and defining their non-negotiables. Some prioritise privacy, others want ocean views or proximity to top schools. When multiple decision-makers are involved, aligning expectations early is key.

I also encourage long-term thinking. Will this property suit them in five or ten years? Is it a stepping stone or a legacy asset? For downsizers, is it truly future-proof?

Beyond finding the right property, I ensure it stacks up— analysing zoning control, other development, and potential risks. If needed, I bring in architects, planners, builders, or legal experts to provide a complete picture before any decisions are made.

My network provides access to off-market opportunities that most buyers will never hear about. It is a world built on discretion, relationships, and knowing what’s coming before the market does.

At this level, time is as valuable as money. My clients are high-performing individuals who can’t afford inefficiencies, so I manage every aspect of the process—from sourcing and inspections to negotiations—so they can make confident decisions without distraction.

What are some of the perks of working in the ultra-prestige property space?

One of the biggest perks is working with incredible properties—waterfront estates, architectural masterpieces, and homes most people only see in magazines. Equally rewarding is collaborating with top professionals in sales, development, design, and finance, and gaining insight into how they solve problems. Their experiences sharpen my own and ensure the best outcomes for clients.

What is most fulfilling, though, is working with self-made, highly successful individuals whose drive and discipline remind me of elite athletes.

It is a privilege to help them make one of their most significant financial decisions—securing a dream home or a strategic investment. It’s about aligning every decision with their vision and long-term goals.

What are you most looking forward to in 2025?

I’m really looking forward to our annual family trip to the Basque Coast in France to visit the in-laws. My daughter is four, my son is one and a half, and I’m amazed that my daughter is now completely fluent in French. I can’t wait to see her fully immersed in the language and culture for a few weeks. Plus, nothing beats the batter and good food, family time, and a European beach summer!