Trying to get around fellow 500 rookie Charlie Kimball at the entrance of Turn 4, Hildebrand drifted too far up the track, into the marbles and into the wall exiting the turn.
Indy rookie Hildebrand: It was one turn too many
Leading by almost four seconds with a lap to go, 23-year-old rookie just needed to negotiate one more lap and the Indianapolis 500 was his. The chequered flag was in sight.
And the first three turns went smoothly. Then Hildebrand came up on another rookie, Charlie Kimball, in the fourth turn. Instead of backing off, he moved to the outside to pass and lost control, slamming into the wall to a collective gasp from the crowd of 250,000.
"It was a helpless feeling," Hildebrand said.
Along came Dan Wheldon, the 2005 winner but without a full-time ride, who appeared headed for his third straight runner-up finish when Hildebrand took the white flag needing only to make it through the last of 200 laps around the 2.5-mile (4km) speedway. Wheldon steamed past Hildebrand's wreck for his second win at the Brickyard.
"It's obviously unfortunate [for Hildebrand], but that's Indianapolis," Wheldon said. "You never now what's going to happen."
So it was Wheldon who took the traditional swig of milk for winning and Hildebrand left standing dry.
John Barnes, owner of Panther Racing, knows his young driver will rethink that moment over and over again, but said, "He did a hell of a job. He'll rethink Turn 4 for a long time, but he put us where we're at. It's just one of those things. You have to hold your head high. He drove the wheels off it. I couldn't be prouder of him."
Nice words to act as a salve to help lessen the sting, but Hildebrand nevertheless was "just frustrated. I just made a mistake and it cost our boys.
"I guess that's why rookies don't win the Indianapolis 500 a whole lot. We'll be back next year, I guess."
Thinking about this year again will be Wheldon, who was dropped by Panther Racing, and had only this one-race deal with Bryan Herta Autosport.
He made the most of it.