Why Whincup's next move is no calculated gamble

"I'd like to think it was an educated risk, not completely left field," jokes Jamie Whincup when reminded that Triple Eight has rolled the dice on a young driver before.

He's right, of course. There's not much that's random about the way Roland Dane does business. Still, there's no denying there was an element of risk when it came to signing a relatively unknown Whincup back in 2006.

Even Dane couldn't have predicted just how well that risk would pay off, netting a record-breaking 122 race wins and seven titles over 15 seasons so far. And you wouldn't bet against Whincup adding to either of those tallies in this, his final season as a full-timer.

And Dane didn't just unearth a loyal, ultra-consistent race winner. He unearthed a motor racing mind he trusts so much he's willing to hand the team he built over to it.

The recent announcement that Dane will step down from his long-held managing director and team principal posts at the end of this year, handing them over to Whincup, doesn't mark the start of the transition process. Rather, it marks the beginning of the final phase.

The process itself has long been in motion. That was made clear when Whincup took what was initially a 15% stake in the business in 2018. It became even clearer in 2019 when he successfully lobbied to join the Supercars Commission. Now there's one last season for Whincup to drive, learn from his Commission role and watch his boss in action, before he grabs hold of the Triple Eight reins.

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Even someone as accomplished as Whincup will surely feel daunted by the prospect of replacing Roland Dane, a person of great influence in world motorsport. A person who arrived in Australia and built a motor racing empire so quickly and effectively thanks to his rare combination of intellect, business intuition, political prowess and no-nonsense people skills.

Dane is someone who gets things done. He knows how to get the cards to fall Triple Eight's way. That's curated a perception, particularly outside the paddock but something in it as well, that all he cares about is Triple Eight. That the second his cars aren't winning, he stomps his feet and yells and screams until Supercars caves in.

But that's an oversimplification that ignores the fact that Dane has a deep love for the series, something that doesn't necessarily need to be separated from his desire for his team, and business, to succeed.

"Roland and I have a different management style but RD doesn't get on the radio or the phone or the TV and express his opinion for no reason. Sometimes it's absolutely necessary and if something needs to be done, it needs to be done" Jamie Whincup

"Roland has a good heart for the business," an industry insider who's worked closely with Dane tells Autosport. "Everyone knows he's got a good mind for the business, but he's got a good heart for the business too. There are no doubts that he's had opinions and thoughts on the direction of the industry with his mind on how it will affect Triple Eight. That's human nature. But the bulk of his ideas and thoughts are for the benefit of the industry, as well as his team.

"When people say 'Roland has made that decision because it's going to benefit Triple Eight', most of the time that is true. But the bit that can be missed is that the decision also benefits the other teams."

Dane's successful push to be as involved as possible in both car homologation and control parts production is the perfect example.

"Does it benefit Triple Eight?" adds the insider. "Of course it does. They build something and people have to pay them. But when it's the best product available, and the teams are going to have pay somebody for it, it's a benefit for everyone."

Intentions aside, there's little question that Dane is ruthless when it comes to fighting Triple Eight's corner. He's famous for it and that leaves Whincup with some big shoes to fill. The obvious question is, will he be up for it? Perhaps the better question is, does he really need to be?

"Hey, I'm me, and I'm going to work hard on making sure I've got good relationships with Supercars, [CEO] Sean [Seamer], [Chief Strategy Officer] John Casey, the likes," said Whincup during the announcement earlier this week.

"Roland and I have a different management style but RD doesn't get on the radio or the phone or the TV and express his opinion for no reason. Sometimes it's absolutely necessary and, for sure, I'll have to fulfil that role, without doubt. If something needs to be done, it needs to be done.

"So, I'll be there in those times but I'll be managing the situation the way I believe is best."

There are two good reasons why Whincup can take that approach. And they share a surname.

What's yet to be clearly defined is what role Jess Dane, Roland's daughter, will play in the new structure of the team. But it won't be an insignificant background role. For one, she's now the second biggest stakeholder in the team with a 30% share (which, combined with Roland's 11%, still leaves the Dane family one per cent clear of new investor Tony Quinn in the overall ownership picture).

Secondly, she too has spent a number of years expanding her footprint within the sport. Just within Triple Eight itself, she runs the commercial side of the team, is heavily involved in the Super2 and GT programmes, and works directly with media. Outside of the team, she chaired a Motorsport Australia commission dedicated to female involvement in the sport and works with the FIA Girls on Track initiative. She's also part of the broadcast line-up for the Australian Racing Group's TV coverage. Oh, and she's also a year off completing a law degree.

"The TV job, the commissions... none of it is an accident," says our insider. "She's fast becoming one of the most influential people in Australian motorsport. Jamie will be the figurehead, but don't underestimate Jess' role in this."

Roland Dane won't be entirely lost to the team, either. He's set to make his own transition into an advisory role, and while he might not be on the ground at every single race meeting, you can bet he'll be well-positioned to get his hands dirty when needed.

"Look at the relationship between Roland and [team manager] Mark Dutton," says our insider. "Over time Mark has become the guy wearing the headset, calling the shots in the garage. But when the moment calls for it, Roland is there, Roland taps him on the shoulder and whispers in his ear.

"Jamie will very quickly learn how to hold his end up and to make sure he doesn't get walked all over. I'm extremely proud and happy to have watched him mature and grow up, not only as a race driver but as a person and as a businessman" Roland Dane

"If Jamie needs a kick up the backside to be more assertive, Roland will still be there. It might not be so public, but Roland will still be there."

None of this is to suggest that Whincup himself isn't capable of the job. He may be one of the nicest guys in the paddock (the common perception from fans that he's arrogant is baffling, to say the least), but he's also a fierce competitor. There's always been a sense that he loves winning more than driving. Pair that competitiveness with what he's learnt through running his own car wash/cafe business outside of motorsport, and the past 18 months he's spent on the Supercars Commission, it's easy to build a case for him being the right man to spearhead the new-look Triple Eight.

That's certainly the view held by Roland Dane.

"Firstly, he's commercially astute," Dane tells Autosport. "Secondly, he's a deep thinker. He thinks about his decisions very carefully. That sets him up well to take a long-term view, which I've always tried to do.

"He's also getting better and better at developing his people skills and the relationships with people around him. Jamie has been very aware of the need to develop and work on that, and it's paying dividends now.

"I think he'll be able to fight his corner. He'll also have some good people around him. In terms of day-to-day management of the race team there's Mark Dutton, plus Jeromy Moore and then Tony Quinn in the background.

"I think Jamie will very quickly learn how to hold his end up and to make sure he doesn't get walked all over. I'm extremely proud and happy to have watched him mature and grow up, not only as a race driver but as a person and as a businessman. Watching that transformation over the years, and now seeing him take this big step, is something that I'm proud of."

Whincup doesn't need to fill Roland Dane's shoes all on his own. That's a three person job, and one of those people is Dane himself.

And if there's a management structure being built to play to Whincup's own strengths - and it sure looks like that's what's happening - then it's hard to picture a future for Triple Eight that isn't remarkably bright.