Roger Penske hired Helio Castroneves to be part of his CART team at the end of the 1999 season. He had finished 15^th in the drivers' championship in 1999 with one podium finish, second place at Gateway. Working with one of the better racing teams, he won three races in 2000 and finished seventh in the drivers’ championship.

In 2001, Penske returned to the Indianapolis 500 for the first time since 1995 with a two car team. Starting from the 11^th position, Castroneves won the Indianapolis 500 and his teammate, Gil de Ferran, finished second. For the year, Castroneves had three CART victories and finished fourth in the CART driver rankings.

Castroneves won his second consecutive Indianapolis 500 in 2002. Combined with a win at Phoenix and five other podium finishes, he finished second in the drivers’ championship. In 2003, he had two victories and six other podium finishes and was third in the driver rankings. His performance in 2004 slipped slightly with one win to finish fourth in the final rankings. Overall, Team Penske’s performance was off and was attributed to a lack of power with the Honda engine. In August, Penske switched to a Toyota engine

Despite having switched engines for the 2005 season, the performance for Team Penske did not improve. Castroneves finished sixth in the driver rankings with one victory. At the end of the season, Penske switched back to a Honda engine. This made a difference. Castroneves finished third in the driver rankings with four wins in 2006. In 2007, he won one race and finished sixth in the driver rankings.

In 2008, Castroneves finished second in the driver rankings with two wins and nine other podium finishes. In October, Castroneves, his sister Kati, and his attorney Alan R. Miller were charged with tax evasion. The federal government alleged that Castroneves failed to report $5.5 million in revenue from 1999 through 2002. During this period of time, Castroneves was paid $1 million per year by Team Penske and Seven Promotions was paid an additional $5 million. Because of the indictment, Castroneves’ future with Team Penske was unclear as most drivers’ contracts have a termination clause if a driver is convicted of something illegal. Penske believed he had gotten poor advice when setting up his offshore companies including Seven Promotions.

Castroneves was arrested while he was practicing for the American Le Mans Series race at Road Atlanta. He was released from jail and allowed to participate in the race which he and teammate Ryan Briscoe won. Castroneves thought that the race helped him to forget his legal woes at least temporarily. He promised to fight the charges and believed he would win.

Castroneves’ defense centered around not having controlling interest in Seven Promotions which was owned and operated by his father. His father testified that the company was a way to repay him for the $1.5 million he had spent on Castroneves’ early racing career beginning with go-karts.  The IRS maintained that even though Castroneves had not received any of the $5 million in licensing money, he was still responsible for paying the taxes.

His trial was scheduled to begin on March 8, 2008. Penske’s request that the trial be postponed until the end of the season was denied. Penske hired Will Power, the Champ Car 2006 rookie of the year, as Castroneves’ replacement as long as Castroneves was unable to drive in the races.

Through the very long winter, Penske talked to Castroneves on almost a daily basis and promised him a job if he was cleared of the tax evasion charges. Penske said, “I’m standing behind him.” Of the 154 races he had run for Team Penske, Castroneves had won 20 including 14 in the Indy car series.

Castroneves was cleared of the charges on April 18. It had been six months since he had been in a race car and had not done any of the off-season testing. Upon hearing the news, Team Penske’s president Tim Cindric texted him “We’re ready for you.” Penske had a private plane fly Castroneves from Florida to California where the team was practicing for the Grand Prix of Long Beach.

Upon arriving in Long Beach, Castroneves pulled on his racing gloves and got into the No. 3 car. While qualifying, he spun into a barrier damaging the car.  Despite this, he qualified eighth and finished seventh. Two races later, he won the pole for the Indianapolis 500 for the third time in his career. He also won the Pit Stop Competition. He claimed the trifecta winning his third Indianapolis 500. He led 66 laps including the final 59. After climbing the fence as part of his celebration, he got back into the car and wept tears of joy. He told Penske, “Thank you for giving me my life back.”