A confidante of both President Barack Obama and first lady Michelle, Valerie Jarrett (pictured on April 28, 2014), the trusted “First Friend,” quickly emerged as the most influential adviser in the Obama White House. | Chandler West/For Sun-Times Media

Sweet: Valerie Jarrett, other Chicagoans look back at Obama years

SHARE Sweet: Valerie Jarrett, other Chicagoans look back at Obama years
SHARE Sweet: Valerie Jarrett, other Chicagoans look back at Obama years

Follow @lynnsweetWASHINGTON — Eight years ago, President Barack Obama settled into the White House with a cadre of Chicagoans from his adopted hometown at his side. Some joined his team later. Some left after a few years in the administration.

None had the unique role that Valerie Jarrett served in through these two terms.

She is Obama’s longest-serving senior adviser, as well as director of the office of public engagement and intergovernmental affairs. Her titles hardly describe her wide portfolio.

A confidante of both the president and first lady Michelle, Jarrett, the trusted “First Friend,” quickly emerged as the most influential adviser in the Obama White House.

Powerful, she outlasted Rahm Emanuel and Bill Daley, who both served as chiefs of staff for Obama, as well as another senior adviser, David Axelrod.


Follow @lynnsweetJarrett met the Obamas in 1991, when she was working in Mayor Richard M. Daley’s City Hall and Michelle interviewed with her for a job in the Hall.

“I would expect to grow old with the Obamas,” Jarrett told me. “They will be my friends for the rest of my life, and I’ll help them in any way I can.”

Here are stories from Jarrett and others from Illinois reflecting on their front-row seats in the Obama administration . . .

VALERIE JARRETT, Jan. 20, 2009, to Jan. 20, 2017

On her duel friend/adviser role: “I think we are all able to compartmentalize. . . . I don’t think it was ever hard for us. . . . I’ve always felt that knowing the president and first lady . . . helped me do a better job. And there were certainly times when helping them as senior adviser and being privy to what was going on in his or her life professionally helped make me a better friend.”

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On foreign travel: “A trip that I went on my own to Dharamsala [India] to deliver a letter from President Obama to the Dalai Lama was extraordinary.”

At Buckingham Palace: “I’ll never forget the first time in the motorcade when the gates opened and I drove into Buckingham Palace with the president’s motorcade and met the queen. And that was a thrill for me.”

RAY LAHOOD. Transportation secretary, January 2009 to June 2013

LaHood, a former Illinois lawmaker, and Obama grew close when Obama was in the Senate.

On golfing with Obama at Andrews Air Force Base: Obama “was always generous about wanting me to play golf. We always had a lot of fun together. You ride in a cart, it’s a four-hour round of golf and you really develop a friendship.”

On attending a private Obama birthday party, where guests included NBA players: “And we were all sitting outside on the lawn having a barbecue with people like LeBron James. That was kind of neat for me.”

On never being the “Designated Survivor,” who skips the State of the Union: “The last thing anybody would have wanted if something would have happened is for a Republican to take control of the government.”

DAVID JACOBSON, special assistant to the president for presidential personnel, January 2009, ambassador to Canada, September 2009 to July 2013.

The Chicago lawyer and banker was a major Obama fundraiser.

At an Oval Office meeting with Obama and Canadian Prime Minister Stephen Harper, one of Harper’s aides looked at the wall and asked Jacobson, “There’s a document on the wall and it says a proclamation, what is that, why is there a proclamation sitting on the wall of the Oval Office?”

“And I said to him, ‘It’s the Emancipation Proclamation, signed by Abraham Lincoln.’ . . . It was such a poignant moment of here we were with the first African-American president of the United States sitting under the Emancipation Proclamation.”

MICHAEL STRAUTMANIS, former deputy assistant to the president and counselor for strategic engagement to Senior Adviser Valerie Jarrett 2009-2013

Strautmanis entered the Obama orbit as a young paralegal for Michelle Obama when she was at a Chicago law firm. A mentee of both, the attorney is now the Obama Foundation’s vice president for civic engagement.

A vivid memory: With Obama when he talked with young men at a Hyde Park High School “Becoming a Man” meeting.”

“He definitely talked about the fact that he got in trouble as a young man but that he was in an environment that was more forgiving, and so right in the middle of it, this kid shot up his hand and it was, sort of right in the middle of him making a point, and so everybody was a little taken aback and [Obama] said, ‘Yes?’

“And the kid said, ‘Are you talking about you?. . . And all of a sudden this distance between them shrunk.”

COMING TUESDAY: More Chicago voices from Obama White House insiders

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