"In 2007, when [the All Blacks] got knocked out by France, who had the cojones to stay with the same coaches? That was a big call and that proved a gutsy call.
"I think we have the players. New Zealand will always have great players. It's a matter of developing a way we play which isn't New Zealand or South Africa. That's not easy in test match rugby, but [Cheika] has a true idea of how he wants to play."
Having played the All Blacks 27 times in a 13-year international career, Gregan is well placed to reveal without hesitation the identity of the best player he ever faced.
"Zinzan Brooke. Zinny was a freak. I would have liked to have played with him. I always give Marshy [Justin Marshall] a ribbing, saying 'How hard was it for you? You had the armchair ride with Zinny. He did everything for you, even throwing passes to the 10. No wonder you were mincing around like you owned the world.'
"He could pass, run, smash someone in defence. His competitive spirit was immense. He defined what a great All Black was."
Gregan will well recall one of Brooke's greatest hits, a long cutout pass in the 1997 Bledisloe Cup test at Carisbrook, which hit Christian Cullen on the chest. The fullback then turned Gregan inside out on a mazy charge to the tryline.
He wasn't about to enter into the debate as to whether Michael Jones or Richie McCaw was the better openside flanker. Of current players, he rates halfbacks Aaron Smith and TJ Perenara highly.
Tim Horan, one of the finest No 12s in history, is his pick as the best he played with. He went from a good but not fully rounded player in 1991 to the best in the world, while overcoming adversity.
"It was a good insight into what greatness is about, but I thought Tim's performance during the 1999 World Cup was incredible.
"He came back from a horrific, career-threatening knee injury in 1994, got to the 1995 World Cup miraculously ... it was almost like he thought the '99 would be how Tim Horan was going to be remembered.
"And wow, he played in a manner that transcended any player in a World Cup. In the semi, he was crook, he shouldn't have played, and he went out and played the game of his life."
Unlike countryman David Boon, who understandably bristles every time those 52 cans are mentioned rather than his 7422 test runs, Gregan does not mind talking about that tackle in 1994 which saved the Bledisloe Cup.
"It was a big moment. It was my fourth test match. I went on to play a lot more. That was one of those moments in sport. It was a Wednesday night game in Sydney under lights. It was the first time it had been done and hasn't been done since," he says.
"I was on the back pages, but it's not like it is now. There was no social media. I wouldn't have said I was trending then.
"It was one of those moments in sport you are not going to replicate 99 times out of 100. But that was your moment and you were in the right position at the right time.
"I always said I wouldn't have been in that position if five other blokes had made their tackles on Jeff [Wilson]. He was a good sport about it. But I never made a tackle like that on him again. I always got the big right foot step from Jeff."
Now they just laugh about the incident on the golf course.
It's well known that he also gets on famously with Marshall, though perhaps not Byron Kelleher as much, who was the subject of Gregan's infamous "four more years" taunt in the dying throes of the 2003 World Cup semifinal.
"It's iconic, but it was gamesmanship. You are in the moment. I've been on the end of some great one-liners. That was between two players, but the cameras thought they would come into this nice romantic moment and it went round the world.
"Every time I go back to New Zealand, I am reminded of it, and obviously the All Blacks have gone back-to-back World Cups, so I really cop a hiding.
"It's competitive, two countries, two players and the semifinals of the World Cup. That moment encapsulated the gravity of the situation. I saw Steph Curry and LeBron James going at it in game six and seven of the NBA finals last year. I love that, because that's what it's all about."
Gregan was possibly more widely admired in New Zealand than Australia. He rated only No 35 on the list of great Wallabies in scribe Greg Growden's book, despite his achievements and longevity.
His legacy won't unduly worry him. He is a successful businessman and TV rugby pundit, has served on the ARU board, and is not reticent when asked his opinion on the state of the game in Australia.
They started with three Super Rugby teams and now have five. That is one too many in some eyes and Gregan concurs.
"Five is tough. If you look at the make-up of the Perth [Force] team, they are trying to develop players, but it is difficult ... Constant expansion hasn't worked. They've got to be smart about the teams they add and how they set up the programme. The poor old Jaguares had to do long-haul travel about 40 times last year. That is really hard to sustain."
He feels a Fiji-based Super Rugby team, after discussing it with former Fiji sevens coach Ben Ryan, is workable, especially with some 160 Fijians plying their trade in Europe.
Gregan and his wife love getting back to Fiji. He first played in the Suva Sevens in 1993 and feels the shortened form of the code offers a good learning curve for young players.
"You start your career through sevens. It's such a great way to learn the game. It's flat stick and you have to make decisions under pressure. It's a fast-track to becoming a very good rugby player."
It didn't do George Musarurwa Gregan much harm.
