Whincup has had the most successful career in Australian touring car history, with a record seven Supercars titles, 124 wins and four Bathurst 1000 crowns.
However, he has not been loved throughout the journey, as Peter Brock and teammate Craig Lowndes, Whincup have been a polarizing figure among fans for much of his 15-year stint with Triple Eight.
That can be partly attributed to the tribalism between Ford and Holden in Supercars, Whincup’s place in the long-standing rivalry complicated by the T8’s transition from blue to red side ahead of the 2010 season.
As for other factors contributing to the “Whingecup” persona, Whincup admits that an “immature” approach to public life early in his career didn’t help endear him to fans.
“It’s a combination [of things]’, Whincup told Motorsport.com.
“When I think about it and analyze it – which I don’t normally do – but… I look back at interviews I did in the early days and I almost cringe.
“I was a young kid, a little immature, and I had only one goal: to get out there and race that car as hard as I can.
“In some ways I did a bad job in the press, hoping they wouldn’t ask me to speak again. If I do a bad job, they leave me alone.
“There’s also the tall poppy syndrome here in Australia. I was kind of loved when I won my first few races when I was the underdog. But Australians, we like to shoot everyone who is on the run and good does things, especially in sports or politics.
“We love to get them back on the ground. It’s just a thing with Australian makeup.
“I could have done things a little differently in the beginning.”
But while he accepts that he ruffled some feathers along the way, Whincup says he hopes others have enjoyed his success and determined, uncompromising approach to motorsport.
“I’d like to think that when it’s all said and done, there are enough people who have sat on the hill over the years and just liked that I gave everything I have in the race car,” he added .
“Whether that was a win, whether I was in the middle of the pack, whether I ended up in the stewards’ room or lost a wheel or ran out of gas, whatever it was, I hope everyone liked that I tried give everything to get to the end.
“Some days it went well, some days it didn’t.”
Whincup will make his final start as a full-time Supercars driver in next Sunday’s Bathurst 1000.
He reflects more on his polarizing relationship with fans in his autobiography Drive of a Lifetime, which goes on sale next week.