Updated

Roger Penske was optimistic the 100th running of the Indianapolis 500 would be one to remember.

Well, he'll remember it. For all the wrong reasons.

Defending race winner Juan Pablo Montoya lost control and crashed in Turn 2. Will Power and Simon Pagenaud were penalized on pit road. And Helio Castroneves damaged his rear wing and had to replace it late in the race, hurting his chances of joining the exclusive club of four-time winners.

Hardly the way to celebrate Penske's 50th year in motorsports.

"My car was awesome, man. We had a great run," said Castroneves, who led 24 laps — third-most in the race — before finishing 11th. "But I'm very disappointed with the way we finished."

No doubt The Captain was, too.

The highlight of the sun-splashed spring day for the winningest owner in Indy 500 history might just have been driving the pace car during the parade laps. Nearly 400,000 fans packed into the old speedway to see the centennial race, and they cheered Penske as he sped by behind the wheel of the Camaro.

Things began going downhill after he turned over the keys.

Power was running near the front on Lap 48 when the field pit during a caution. He was told "all clear" by his spotter to exit his stall, but wound up colliding with Tony Kanaan. There was no damage to either of their cars but race stewards penalized Power, shuffling him to the back of the field.

Ten laps after the race returned to green, Montoya lost his car and slammed hard into the wall.

The two-time winner was fortunate nobody else collided with him as he slid into the grass. Montoya climbed out of his wrecked car and waved to some of the fans crowding along the fence, then climbed into an ambulance for the kind of ride nobody likes to take at Indianapolis Motor Speedway.

"People in race cars do a lot of dumb things and we were being careful," Montoya said. "I started making up some ground again and the car was actually pretty good. It was really sloppy, but it felt OK. I went into 2 with a big push and when I got on the gas, it just came around."

The problems for Team Penske continued under caution. Series points leader Simon Pagenaud, once again running near the front, was penalized for an unsafe release after his stop and sent to the back.

The penalty ultimately put him off pit sequence with the rest of the leaders.

It appeared Castroneves might save the day for Penske when he continued to run with the leaders and the laps ticked away. But the three-time winner was nudged from behind by JR Hildebrand under green, causing a piece of his rear wing to come loose and flap in the breeze.

He was bailed out when Takuma Sato slapped the wall to bring out the caution, allowing him to change the wing in the pits. But the slow stop and just 36 laps left cost him a shot at the win.

"I have to be careful what I say," Castroneves said, fuming. "I don't want to regret it later on."

Power wound up 10th, the best of the Penske drivers, with Castroneves right behind him.

"I'm really, really, really upset. It's a race that's so important," said Castroneves, who had talked about delivering on Penske's 50th anniversary. "With that incident, we missed the opportunity to race for the win. The way we were running, I felt we had a phenomenal chance to do that."