While acknowledging that the struggle to keep players existed during his playing days, McCaw says the current climate for NZ Rugby is "unfortunate".
"I think it's always been a challenge," he tells the Herald ahead of his next sporting challenge at the Coast to Coast.
"It has been for a while and it's always going to be. It's just unfortunate the things you have to deal with as New Zealand Rugby. I think we're probably never going to compete dollar-for-dollar for what's on offer for some of these guys up in the Northern Hemisphere.
"You've just got to make it really hard for guys to make that decision to go overseas."
Like everyone else, he doesn't blame players for leaving - family and financial security always trumps rugby, especially because of the precarious nature of the sport.
McCaw's solution is simple: there will never be anything that rivals playing in the black jersey – and its aura, culture and perennial success is New Zealand Rugby's point of difference.
"We've always said having an environment that's really enjoyable and fulfilling, [where] you get looked after, and the chance to play for the All Blacks, that's the things that we've got in our favour as New Zealand Rugby.
"And some will [leave], and rightly so if that's the right thing for them. But if we keep the environment good and the All Blacks successful, it's quite a hard team – when you've had a taste of it – to turn your back on.
"They're the things that you can control and if you do that, then hopefully we encourage a good number to stay behind and stay here and keep playing. But I think it's always going to be a challenge and we'll be talking about it for a long time but we've just got to keep hopefully inspiring people that want to perform in the black jersey because I think it's a pretty big carrot to stay here."
McCaw represents an increasingly rare breed of footballer, a one-club-man whose loyalty and longevity only seemed to make his game even stronger.
If there was ever a success story for the benefits of fighting for the black jersey throughout your career, it would be McCaw, the 148-cap legend who many consider to be the greatest ever All Black. Leaving, he says, was never an option.
"I didn't have any real burning desires to go and play anywhere else. If I was going to play properly, and you want to do that wherever you're playing, I would want to play in New Zealand because that's the team I enjoyed.
"I think when I gave up, I was at the point where I knew it was going to become tougher and tougher to keep that motivation and all the training you needed to do, just cause that's what happens. And I thought, well, if I can see that it might start to happen here, it would be even worse for a team you don't know a lot about.
"It was pretty easy decision not to even consider [going overseas]."
