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US President Donald J. Trump awards the Presidential Medal of Freedom to American businessman and entrepreneur involved in professional auto racing Roger Penske US President Donald J. Trump R awards the Presidential Medal of Freedom to American racing magnate Roger Penske L during a ceremony in the Oval Office of the White House in Washington, DC, USA, 24 October 2019. The Medal of Freedom is awarded by the president to citizens who make an especially meritorious contribution to the security or national interests of the United States, or world peace, or cultural or other significant public or private endeavors. Credit: Shawn Thew / Pool via CNP Washington District of Columbia United States of America EDITORIAL USE ONLY Copyright: xx 102419stx13 ShawnxThewx cnpphotos153017
Imago
US President Donald J. Trump awards the Presidential Medal of Freedom to American businessman and entrepreneur involved in professional auto racing Roger Penske US President Donald J. Trump R awards the Presidential Medal of Freedom to American racing magnate Roger Penske L during a ceremony in the Oval Office of the White House in Washington, DC, USA, 24 October 2019. The Medal of Freedom is awarded by the president to citizens who make an especially meritorious contribution to the security or national interests of the United States, or world peace, or cultural or other significant public or private endeavors. Credit: Shawn Thew / Pool via CNP Washington District of Columbia United States of America EDITORIAL USE ONLY Copyright: xx 102419stx13 ShawnxThewx cnpphotos153017
Just days ago, President Donald Trump signed an executive order giving the green light to the Freedom 250 Grand Prix, a new IndyCar street race in Washington, D.C., for the nation’s 250th anniversary. Now, Roger Penske, who doesn’t write letters very often, has written an emotional one to the president, expressing heartfelt gratitude for this powerful initiative.
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White House reposted Roger Penske’s letter
Roger Penske addressed the publicly shared letter dated 2nd February 2026, to President Donald Trump. The official account of the White House on X reposted the letter. In it, Penske thanked him for the recent hospitality and offered praise for President Trump’s vision in advancing initiatives that prioritize America.
“It was great seeing you last week during our visit to the White House. I appreciate all the hospitality your team has extended to us. Thank you for all that you and your administration are doing to put “America First,” to protect our borders, and return investment to our great country,” Roger stated in a letter.
What gives weight to Penske’s tone is not mere politeness but the political and cultural context surrounding the event he references.
Roger Penske’s letter to President Donald J. Trump 🇺🇸 pic.twitter.com/amRBYVziZ5
— The White House (@WhiteHouse) February 3, 2026
“The announcement of the Freedom 250 Grand Prix was a big day for our country and for INDYCAR. It will certainly be a great celebration and will bring incredible economic value to Washington D.C. Thank you for your support in making this happen,” the letter further stated.
This race isn’t merely ceremonial. The Freedom 250 is poised to be the first major motor race ever held on the streets of Washington, D.C. IndyCar and Monumental Sports & Entertainment have also announced a strategic partnership to market and operationalize the Freedom 250, highlighting the broader business and cultural ambitions behind the event.
Bud Denker, President of Penske Corporation and chairman of the event, said, “This is an incredible partnership built to make history on the streets of our nation’s capital.”
Penske’s letter is now public, and it shows two key points. First, the race has moved beyond just a sporting event and is now part of a national discussion. Second, the way Penske wrote and when he sent the letter suggest that he sees this project as more than just celebrating motorsport. He views it as a way to connect his organization with national leadership.
Behind the deal between Roger Penske and Donald Trump
The Penske letter came at a time when President Trump was using his executive power to push the Freedom 250 Grand Prix forward. He focused on overcoming legislative pushback and worked to secure important partners to support the event’s future.
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In late January, President Donald Trump signed an executive order authorizing the first-ever IndyCar street race in Washington, D.C., scheduling it for August 21–23 as part of America’s 250th anniversary celebrations. The move effectively pushed the event forward.
The order gave federal agencies the immediate task of finding a suitable race route through the capital. The Departments of the Interior and Transportation have a few weeks to map this route.
Penske Entertainment’s $300 million empire gained access, partnering with FOX Sports visionary Eric Shanks, who co-dreamed the event.
Transportation Secretary Sean Duffy reflected on it and said, “Freedom doesn’t ring, it revs! IndyCar is about competition and pushing limits, the same things that have always defined America.”
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