This copy is for your personal non-commercial use only. To order presentation-ready copies of Toronto Star content for distribution to colleagues, clients or customers, or inquire about permissions/licensing, please go to: www.TorontoStarReprints.com

Roger Penske has more than seven decades of racing memories, perhaps beginning with the one about not being able to see any of the action.

When he was 14 years old, his father drove the family’s 1949 Ford off Georgetown Road, past the gates and into the infield at Indianapolis Motor Speedway to watch the Indy 500.

“(I will) never forget that first day,” Penske said. “I remember having terrible seats — the worst seats in the track. I don’t even think I could see the cars go by.”

How the view changed. These days, Penske is the 85-year-old race-team and track owner, corporate entrepreneur, financial mogul, do-everything, be-everything Indy legend. He is a cunning businessman who built an enormous transportation empire worth billions of dollars. He is a man who, many say, brought the corporate world to racing — and brought racing to a new level.

“Roger is just a competitor,” said Rick Mears, Penske’s three-time Championship Auto Racing Teams (CART) champion and four-time Indy winner. “But above all else, he loves running the Indy 500. He loves winning.”

In that vein, Penske has few equals. In many ways, he was born to run. Raised near the banks of Lake Erie in the affluent Cleveland suburb of Shaker Heights, Ohio, Penske was a dreamer before he was a winner. He had his father to thank.

“He told me I could have anything I earned enough money to buy,” Penske said. And he would. Penske earned, bought, sold, raced and won early on in life. Racing quickly became an obsession.

Beginning in 1958 at Akron Speedway and continuing in Sports Car Club of America (SCCA) races and other smaller circuits, Penske was an accomplished driver with a devilish desire.

He won his first race at an SCCA Regional at Lime Rock, Conn., driving a Porsche. Two seasons later, he was named the “Sports Illustrated” SCCA Driver of the Year. More titles would follow: a U.S. Auto Club road-racing title, a NASCAR Grand National Series race, then five races driving a Chaparral Corvette GS in 1964. Penske was becoming one of America’s most successful young road warriors. Then, amazingly, he called it quits.

“I wanted to pursue the business end of things,” he said. “I thought I might prolong my life a little longer if I wasn’t behind the wheel.”

Behind the scenes, he would dominate.

With Team Penske formed and racing a key element of his overall business plan, he found early success with driver Mark Donahue, winning two consecutive United States Road Racing Championship titles and three SCCA Trans-Am championships.

After three years, Penske and Donahue moved into open-wheel Indy-style racing, running in two United States Auto Club sanctioned road races in 1968. The following year, the team entered the Indianapolis 500 for the first time and Donahue finished seventh, earning rookie-of-the-year honours. Three years later, they won.

A flood of titles followed in every series possible, but Indy was the centre of it. Penske’s stable of drivers became champions.

Over a decade, beginning in 1984, he was in Victory Lane in Indianapolis seven more times. His teams were referred to as the New York Yankees of racing. He was unstoppable. By 1995, however, it all came to a screeching halt.

A year after starting 1-2-3 and getting Indy victory number 10 from Al Unser Jr., Penske walked away from the speedway empty-handed. “Probably the longest walk of my life,” Penske said of his failed qualification at Indy in 1995 with Unser and Emerson Fittipaldi, who were winners of four of the previous six Indy events.

The free-fall of perhaps the sport’s greatest franchise began a season before a split with the new rival Indy Racing League (IRL) that divided North American open-wheel racing right down the middle. And Penske, who decided to stick with CART, which could no longer race at Indy since the race had become the IRL’s event for 1996, was about to endure the hardest time of his life.

A year later, Fittipaldi was seriously injured in a crash and retired. In 1999, on his own with CART, Penske and Unser split, which was a difficult end to a partnership that earned Penske two Indy victories and one of his record seven CART titles. But when rookie driver Gonzalo Rodriguez was killed practicing at Laguna Seca, Calif., then Canadian Greg Moore (who had agreed to race for Penske in 2000) died during the final race of 1999, everything was crumbling.

Fifty-four times Penske’s cars went to the track and came home without a win. “My life seemed to be sliding somewhere I had never known,” Penske said. “Those were a few years I wanted to forget.”

But, just as suddenly, it all made sense again.

Willing to race under the IRL’s rules to get back into the Indy 500 (“Indy’s a track you can’t stay away from forever,” he said then), Penske was once again champion, taking the 2001 Indy 500 with driver Helio Castroneves’ first-place finish and teammate Gil de Ferran’s second.

Seven more followed, the last in pre-pandemic 2019.

To those who knew him well, the move to IRL was hardly a surprise. To those who had to race against him, it was a scary proposition.

“Roger Penske doesn’t unload anywhere unless it’s a serious deal,” said Unser Jr. “He has brought a lot of attention back to (Indy). But Roger Penske brings attention wherever he goes.”

More victories followed, in open-wheel racing, American Le Mans endurance racing and NASCAR and there appears to be no end in sight.

It would have been hard to predict at the time Penske hung up his driving suit of what would happen down the road, but it was a life choice that has undoubtedly brought him more challenges, more victories and ultimately more success.

Copyright owned or licensed by Toronto Star Newspapers Limited. All rights reserved. Republication or distribution of this content is expressly prohibited without the prior written consent of Toronto Star Newspapers Limited and/or its licensors. To order copies of Toronto Star articles, please go to: www.TorontoStarReprints.com