From the Newbridge College Under-13s to the current Heineken Cup champions, the number 8 has been something of 'a lucky general' for the sides he has led.
Indeed, his record as stand-in captain with Leinster reads played 12, won 12, an unblemished run which includes last month's interprovincial derby win over Munster at the Aviva Stadium.
Probed about his proud record as leader of his province, Heaslip quipped: "I was hoping to avoid (being asked about) that! I got a nice text off (Leinster Chief Executive) Mick Dawson about it, 'no pressure regarding the record'.
"But look, I'm not too worried about the outcome. I'm more worried about the process of it and the little jobs, breaking the game up into five-minute segments.
"The first five, ten minutes worrying about our launch plays, our set plays and if we look after the small stuff the big stuff will take care of itself."
Heaslip is one of the natural leaders in the Irish squad, a vocal presence on and off the pitch and comes ready-made for the role with five full seasons of Test rugby behind him, a Grand Slam, a Lions tour and three Heineken Cup successes.
Of the team selected to face the 'Boks, only Heaslip and Gordon D'Arcy boast 50 caps or more. But despite missing a number of senior players, the 28-year-old back rower is confident he will have plenty of back-up this weekend.
"I've said it before when asked, there's definitely leaders on the field. I know that Rory (Best), Paul (O'Connell) and Brian aren't around this weekend," he explained.
"But there's other great leaders in there who can guide the game around the pitch, take it on and aren't afraid to voice their opinions during meetings or on the field.
"We talk about having ownership of the jersey and that's what we're going to do on the day.
"That's the main thing, that they all want to, as a group and a collective, be able to come into the changing room afterwards, take the jersey off and put it up on the hook and know you've done the jersey proud."
He added: "I've been lucky to have some of the best captains around. Brian's been captain as long as I've been with Ireland, Paulie as well, Paulie has captained the Lions, Leo (Cullen) week in, week out.
"I've had Jono (Gibbes) who has been captain of New Zealand Maoris as my coach as well so I've had these great captains around me. Hopefully I've picked up one or two tricks off them.
"To be honest I'm quite humbled by it all. The last time I played for Ireland, I got to lead them out for my 50th cap and I remember running out on the field just thinking it was the best feeling I've ever had in my life.
"So, to get to do so as captain now, it's Roy of the Rovers type stuff."
Heaslip was in Tesco buying an engagement card for a friend when Declan Kidney got in touch to inform him of the captaincy decision, and the Naas man likened the feeling to that of winning his first Ireland cap.
But he was quickly brought back down to earth by his father Richard, a retired Irish Army Colonel.
"The first thing dad said to me, he goes, 'Congratulations on your captaincy but I'm still a colonel, so I pull rank'. They were literally his first words so I was put back in my box then!"
Richard's leadership qualities have obviously rubbed off on his son who was born in Israel while his father was there on duty with the United Nations.
"He's never sat me down and told me anything but it was probably like the way I used to learn rugby off my brother - monkey see, monkey do," admitted Jamie.
"Being around my father so long, seeing him work in places like Kosovo, Cyprus, Israel, Belgium, living over there and seeing what he was working in, I obviously picked up a couple of things.
"It's probably why I'm able to compartmentalise things, deal with rugby as a job and then step away from it afterwards.
"That's how I saw dad do it. He would be the ultimate professional in what he was doing, then step away from it and be the family man that he is."
Ireland head coach Kidney had no hesitation in giving the captaincy to Heaslip, a player whose laidback image often obscures just what a hard-working and dedicated professional he is.
"Although he'd probably deny it, Jamie is the consummate professional. When he turns up for work he's really zeroed in," commented Kidney.
"That's a good place to start - leading by example. He's been part of this group for a few years now.
"We talked with Jamie about the captaincy and he's shown good potential with Leinster. There were other guys holding their hands up for the job but the time is right for Jamie.
"Who should be the next captain has been in my mind for a while. We'd been working on a new leadership group over the past year to make sure that when the day did come, it would be more of a natural progression than a shock to the system."