A phone call with former Roosters chief executive Bernie Gurr more than 20 years ago can be seen as the start of Cleary's journey from reluctant coach and prospective real estate agent to a great of the modern game.
Cleary's decision to accept Gurr's offer to lead the Roosters' lower-grade sides opens up several what-ifs, not least if he and son Nathan would have gone on to become legends at Penrith.
Ivan and Nathan Cleary after the Panthers notched their premiership hat-trick in 2023. (Mark Evans/AAP PHOTOS)
Ivan has the chance to become the first head coach since St George's Norm Provan (1962-65) to win four straight NRL titles when the Panthers meet Melbourne in Sunday's grand final.
Which is no mean feat, considering he believes the beginning of his coaching career was purely accidental.
In 2002, after he had signed off playing with the Warriors, Cleary was preparing to take his family to England and play out a one-year deal with Super League club Huddersfield.
Cleary figured he would do a season in the UK, travel in Europe, then return home to start a career in property.
But out of the blue, Cleary got a call from Gurr telling him there was a chance to take his life in a different direction.
"He (Gurr) pretty much just asked me if I was interested in coaching, which I'd done none of ... bar playing, I wasn't prepared one bit," Cleary told AAP.
"The Roosters were the premiers at the time and it was a club I'd played for, so for me it was too good an opportunity to turn down, and I retired pretty much there and then.
"I was at a fairly mature age at that point, Dean Pay was coaching the under-20s and was going back to the bush, so I guess they needed to fill a spot.
"Maybe I was the last one they could find? I don't know.
"As much as it was exciting, I was extremely humbled that they'd even think of me in that way."
Ivan Cleary hadn't planned on coaching after his playing career finished. (Mark Evans/AAP PHOTOS)
On the other side of the world, Huddersfield had billed Cleary as their star signing after winning promotion back to the English top flight.
Huddersfield's then chief executive described the capture of Cleary as the "biggest signing in the club's history", but they were caught completely off-guard by his decision to back out of his deal.
"This is a devastating blow to our club and one which came out of the blue," a Huddersfield statement said at the time.
Cleary, though, didn't look back.
He won the NSW Cup in his second season at the Roosters with a side containing Ben Hannant, Sio Soliola and the Paea brothers.
After that he enjoyed time at the Warriors, Wests Tigers and Penrith, where he and Nathan have won three NRL titles and can add a fourth with a win on Sunday.
Which sure beats real estate.
"I still haven't got a proper job to this day," Cleary said. "I've been pretty lucky."
