Now that Castroneves is back in town and Penske has assured the exuberant Brazilian racer of making at least two more Indy starts, Castroneves has adjusted his goal.
"I want to win [this year] because winning gives me an opportunity to go for five next year, and I know I'm capable of it," he said. "Racing is still my passion, racing is still my love, and hopefully I can break the record."
Time might be running short on Castroneves' quest, but he certainly knows his way around the historic Brickyard. And he has a lot going for him.
Al Unser won his fourth and final 500 in 1987, becoming the oldest winner in race history five days short of his 48th birthday.
Castroneves is 43 and works for the winningest team in 500 history, a team that owns four straight wins at Indianapolis Motor Speedway -- last year's 500 and Brickyard 400 on the historic oval and the 2018 and 2019 IndyCar Grand Prix on the track's road course.
Castroneves' mastery of Indy has turned him into a perennial race-day favorite.
"He knows when to take risks and when not to," four-time Indy winner and driving coach Rick Mears said. "But he also works hard and he cleans up the small things around here that make a big difference. He's really open-minded about all that, but he also drives very smooth, which is another plus."
The resume proves it.
Castroneves won his first two Indy races in 2001 and 2002, making him the first driver since Unser in 1970-71 with back-to-back victories.
He finished second to teammate Gil de Ferran in 2002 after capturing the first of his four pole wins. Only Mears (six) has captured more poles.
Castroneves also won in 2009, finished second in 2014 and 2017 and has eight top-five finishes and 14 top-10s in 18 career starts.
If this week's practice speeds are a sign of what's to come in qualifying this weekend, Castroneves could find himself in yet another pole shootout.
He was fourth on the speed chart Tuesday, fifth Wednesday and in the top five most of Thursday. Castroneves' best lap of the week, 228.441 mph, is eighth overall, and the Penske cars have performed so well they actually parked early each of the first two days of practice.
It's a solid start to Castroneves' latest attempt to join Mears, Unser and A.J. Foyt in the four-time winners club.
"Hey, it's the 10th anniversary of No. 3," Penske president Tim Cindric joked Wednesday, drawing laughter from Mears and Penske before explaining why Castroneves has been so good for so long on the series' trickiest track. "The risk-reward ratio here is definitely the highest, and he never holds anything back. But he's also a student of the sport and keeps finding little things to work on with these cars and the details that really matter."
That's one reason Penske continues to bet on Castroneves each May.
A year ago, after moving from the IndyCar Series to sports cars full time, Castroneves finished fifth in his season debut at the Grand Prix and then wound up crashing in the 500. He finished a career-worst 27th. Afterward, Castroneves used a television interview to plead for one more chance.
There won't be a repeat May 26. On Wednesday, Penske told The Associated Press he expects Castroneves to return in his familiar No. 3 car next year -- win or lose. And it might not be his last chance, either.
"That's a subject matter I hope we won't have to discuss for a long time," he said. "But we made a commitment to Helio based on the sports car program, and that was a three-year plan."
So Castroneves hopes to make the most of it.
"There are two ways to look at it. The good way is I keep trying, the bad way is I'm still trying every year," he said. "But you can't put the cart before the horse. Let's see what happens right now, and I'm planning to win No. 4."