Team Penske has a phenomenal record in racing. Since the team was formed in 1965, it has won over 540 races and 40 championships across a variety of racing leagues—IndyCar, CART, NASCAR, Formula 1 and others. Despite this record of achievement, there was one period when the racing endured a downward spiral. It must have been very painful for Roger Penske and for the CART team.

The high point was 1994 when the team not only won the Indianapolis 500 and the championship but their three drivers—Al Unser, Jr., Emerson Fittipaldi and Paul Tracy—took the top three championship spots. Qualifying for the Indianapolis 500 in 1995 was disappointing as the team which then consisted of Unser, Jr. and Fittipaldi didn’t make the field of thirty-three. Despite this disappointment, Al Unser, Jr. finished second in the driver championship with four wins and seven podium finishes. Fittipaldi finished eleventh with one win and two podiums. At the end of the season, Roger Penske and Carl Hogan formed a new team with Fittipaldi as the driver. For the 1996 season, Paul Tracy rejoined Team Penske.

The results for the 1996 season would make the 1995 CART season seem like the good old days as the team did not win a single race. Tracy led the first 83 laps of the season opener before a gear selector broke. Unser, Jr. was in the lead on lap 195 of 200 at the Miller 200 at Milwaukee but a decision to use black (hard) tires cost him the victory as Michael Andretti, riding on reds (soft) tires, won.

A decision by Tony George, the president of the Indianapolis Motor Speedway, to form the Indy Racing League and to give the teams participating in the league 25 spots in the Indianapolis 500, resulted in the CART teams choosing to run the U.S. 500 as direct competition to the Indianapolis 500. Tracy finished in seventh place, down three laps, Unser eighth down four laps, and Fittipaldi tenth down nine laps.

The Marlboro 500 was disastrous for Team Penske. Tracy lost control of his racer during practice and slammed the wall backward resulting in a spinal fracture. During the race, Fittipaldi and Greg Moore touched wheels sending Fittipaldi into the wall. He suffered a broken vertebra in his neck, a broken shoulder, and a partially collapsed lung ending his season. Despite not winning a race, Unser Jr. was in second place with three races remaining in the season. He lost his chance to win the title when his engine blew up on the last lap of the Texaco-Havoline 200.  Unser Jr. finished fourth in the driver’s championship with four podium finishes and Tracy finished thirteen with one podium finish despite missing two races. Fittipaldi finished the season in 19^th place without a podium finish.

After a disappointing 1996 season, Team Penske appeared to be on an upward track in 1997. Paul Tracy had a propensity to crash and that certainly impacted his results for the year. He placed second at the Marlboro Grand Prix of Miami. He was leading the Australian IndyCarnival when he crashed with Alex Zanardi. He would also crash at the Grand Prix of Long Beach. Starting from the pole, he dominated the Bosch Grand Prix at Nazareth. He followed up this win by a victory at the Rio 400 after Bobby Rahal ran out of fuel on the last lap. He picked up his third win of the season at the Motorola 300 at the new Gateway Speedway outside of St. Louis. Midway through the season, Tracy was at the top of the driver rankings. Unfortunately, he did not win a race for the remainder of the season and finished up fourth in the driver rankings with three wins and four podiums. Unser Jr. continued his downward slide. After having won the driver championship in 1994, he had gone 30 races without a win. He ended the season in 13^th place with one podium finish, third place at Nazareth. At the end of the season, Tracy was released from the team.

For the 1998 CART season, Team Penske fielded two cars with Unser Jr. and Andre Ribeiro at the wheel. John Travis, a former Lola engineer designed a new Penske chassis for Team Penske. Additionally, there was a new Mercedes engine. After testing the new chassis/engine combination, Unser Jr. believed he had a competitive car. But the car was not competitive and he was shut out. He finished 11^th in the driver standings and had only two podium finishes—a second at Motegi and a third at Milwaukee.  Riberio’s top finish was seventh and he finished 22^nd in the driver standings. At the end of the season, Riberio retired from racing and returned to his native Brazil where he went into the car business with Penske.

For the 1999 season, Team Penske fielded a single entry in the CART season. The car was driven by Al Unser, Jr. who was in the last year of his contract. The season started off very badly. On the second turn of the pace lap at the season opener, Unser Jr. crashed with Naoki Hattori and suffered a broken ankle and a torn ligament in his right knee. He finished 21^st in the season rankings without a podium finish. Fed up with losing, Penske purchased a 1999 Lola chassis which they planned to test against the Penske chassis. It was pretty obvious midway through the season that Unser Jr.’s contract would not be renewed. Penske decided to use the remainder of the season to test young drivers. Tarso Marques, who replaced Unser after his crash, failed to score any podium finishes in the six races he drove. Penske also tested Alex Barron who participated in nine races but didn’t have a podium finish.

The downward spiral from 1995 to 1999 was complete. For the 2000 season, Penske would completely retool. New drivers, new team leader, new engine, new chassis and new engine. Penske selected a Honda engine to replace the Mercedes engine to be paired with a Reynard chassis. He hired Gil De Ferran, who had finished eighth in the driver rankings in 1999 with one win and four podium finishes, and Helio Castroneves had one win for a 15^th driver ranking. His new team leader was Tim Cindric who worked for Bobby Rahal.