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Making Obama

Obama 5: Up Or Out

After his failed run for Congress in 2000, former President Barack Obama faced debt and an endangered political career. Obama, who was a state senator at the time, found himself questioning whether to attempt moving forward or leave politics completely. He continued to set his ambitions higher and planned to run for the U.S. Senate.

Episode five of Making Obama dives into the essential next steps Obama had to take to advance his political career. Hear how he built a political record and won over some powerful backers who helped make him a viable candidate for the U.S. Senate.

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This podcast, from the producers of Making Oprah, tells the story of Obama’s meteoric rise from Chicago to the national stage.

Former Illinois Senate President Emil Jones on Obama asking for his help in his U.S. Senate campaign

Jones: One day he came to see me and he said, “Man, you got a lot of power now.” And I said, “What kind of power do you think I have?” He said, “You have the power to make a United States Senator.”

And it was startling to me, you know. And we kept talking. I said, “Do you know of anyone I can make?” And Barack said, “Me.” So I said, “Let’s go for it.” So that’s what happened.

Valerie Jarrett on her concerns with Obama running for the U.S. Senate

Jarrett: I recall when I first heard from Mrs. Obama that he was thinking about the U.S. Senate race. I thought, “Well, that’s ill-advised.” If he runs for the Senate so soon after losing the Congressional seat, then his political career really will be over if he has two loses back to back. So I thought it was too soon and she agreed, and the two of us collaborated to have a brunch at my home with some of Barack Obama’s closest friends to talk through how we could talk him out of this ill-advised idea.

But he thought it through. ... And in the space of about two and a half hours, we all went from “don’t do this” to “what a great idea!”

Obama on his decision to run for the U.S. Senate

Obama: I traveled statewide to visit my colleagues in the state Senate. And I’d gone down state and I talked to people and looked around. I figured I can talk to these folks. It may seem like I’m a Chicago lawyer from the South Side with a funny name, but when I got down there, I could connect. So, I had a feeling that it would be possible, not necessary probable, but possible for me to win this race.

David Axelrod on agreeing to work on Obama’s campaign

Axelrod: I was depressed about the state of our politics, and Barack called and said he was thinking of making this race for the Senate. I really thought there was a path for him if certain things fell his way. I told my wife, Susan, that if I could help Barack get elected to the U.S. Senate, that would be something that could recharge my batteries. There were no African-Americans in the Senate at that time.

Pete Giangreco on working as a political consultant for Obama

Giangreco: You know as a political consultant, at first you just want to make enough money to make ends meet and pay the bills. And after you win a few races and you feel like you get established, there is kind of this quest for the holy grail. And that holy grail was Barack Obama. He was the one you’ve been looking for your whole career.

There was a freshness and a newness and an about-timeness about a person of color who was ready to, kind of, galvanize where people wanted to take the country. There was a dimension of dream, like if he wins, anything’s possible. … It’s a once-in-a-lifetime thing. It’s the kind of thing you tell your grandkids about.

Full list of people heard in this episode:

  • Former President Barack Obama
  • David Axelrod, political strategist  
  • Delmarie Cobb, political consultant  
  • Cook County Sheriff Tom Dart
  • Chicago Mayor Rahm Emanuel
  • Pete Giangreco, political consultant  
  • Hermene Hartman, editor and founder of N’DIGO
  • Christie Hefner, former CEO of Playboy Enterprises
  • Former Illinois State Sen. Rickey Hendon (5th District)
  • Rev. Jesse Jackson Sr.  
  • Valerie Jarrett, close friend of Barack and Michelle Obama
  • Former Illinois Senate President Emil Jones  
  • Marilyn Katz, public relations consultant
  • Al Kindle, political operator  
  • Attorney General Lisa Madigan
  • Marty Nesbitt, close friend of Obama
  • Penny Pritzker, billionaire businesswoman  
  • Bettylu Saltzman, activist in Democratic politics
  • Chris Sautter, media consultant to Obama  
  • Dan Shomon, former legislative aide and campaign manager for Obama
  • Former Illinois State Sen. Donne Trotter (17th District)
  • Laura Washington, journalist

These interview highlights have been edited for brevity and clarity by Bea Aldrich. Join the conversation at #MakingObamaDon’t want to miss an episode? Subscribe for free on Apple Podcasts, or wherever you listen.

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