Roger Penske
American racing driver and businessman
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| 2024 | Roger Penske won his fifth NASCAR Cup Series Championship as an owner. |
| 2023 | Penske won his fourth NASCAR Cup Series Championship as an owner. |
| 2022 | Roger Penske won his sixth IndyCar Series Championship and his third NASCAR Cup Series Championship as an owner. |
| 2020 | Penske endorsed Donald Trump in the United States presidential election and contributed $45,000 to Trump's campaign. |
| 2019 | Penske received the Presidential Medal of Freedom, the highest civilian honor in the United States. |
| 2019 | Roger Penske won his fifth IndyCar Series Championship as an owner and was inducted into the NASCAR Hall of Fame. |
| November 4 2019 | Roger Penske acquired the Indianapolis Motor Speedway, the Indianapolis 500-mile race, and IndyCar from the Hulman Family for an undisclosed amount, marking a significant milestone in his business portfolio. |
| 2018 | Penske won his second NASCAR Cup Series Championship as an owner. |
| September 16 2018 | Driver Brad Keselowski won the South Point 400 at Las Vegas Motor Speedway, giving Penske his 500th race victory across all racing series. |
| 2017 | Roger Penske won his fourth IndyCar Series Championship as an owner. |
| 2016 | Penske achieved his third IndyCar Series Championship as an owner. |
| 2014 | Roger Penske secured his second IndyCar Series Championship as an owner. |
| November 18 2012 | Roger Penske won his first NASCAR Sprint Cup Championship with driver Brad Keselowski. |
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