Obama team reuniting in Chicago to mark 15th anniversary of historic presidential win

Fifteen years after Barack Obama’s historic presidential victory, marked by a giant celebration in Grant Park on Nov. 4, 2008, thousands of Obamaworld veterans are gathering this week in Chicago for their first official reunion.

Natalie Bookey-Baker, a vice president at the Obama Foundation who worked for then-first lady Michelle Obama in the White House, said about 2,500 alumni are expected.

They are veterans of Obama’s two Chicago-based White House campaigns, his two terms as president, related political operations and his foundation.

Reunion activities — formal and informal — will run Thursday through Saturday. The main events will be Friday at McCormick Place, taking place after the Obama Presidential Foundation’s 2023 Democracy Forum.

The reunion comes a year before the 2024 presidential election, with ongoing threats to democratic institutions contributing to deep and polarized political divides.

A rematch seems likely between President Joe Biden, Obama’s former vice president, and Donald Trump, the ex-president and current front-runner for the GOP nomination — even with all his criminal indictments.

David Axelrod, Obama’s top strategist for his 2008 and 2012 campaigns, said “Democracy is an ongoing battle between hope and cynicism” and now, “it often feels like cynicism is on the march.”

At the reunion, “It’s important for us to kind of get together and renew that commitment, renew that faith, that there will be a better day,” said Axelrod, a CNN senior political commentator.

“Everyone is looking for a little inspiration,” said Johanna Maska, an early hire in Obama’s 2008 presidential campaign who was part of the Iowa advance team. “And most likely we’ll get it in talking to one another, the diverse army who helped elect President Obama.”

Maska went on to lead the press advance team in the Obama White House. She is now a NewsNation contributor and CEO of her own firm, Global Situation Room.

Like Maska, Eric Lesser has been in Obamaworld for 17 years, one of the original hires, dating to those first crucial 2008 votes in Iowa and New Hampshire.

“The idea of hope and change,” said Lesser, referring to the signature slogan of the 2008 campaign, “can be seen as quaint or even far-fetched in an era of red-hot division and pessimism. But maybe in getting the band back together, we can rekindle some of that positive spirit.”

Lesser handled ground logistics on the Obama campaign plane and went on to work in the White House, first for Axelrod. Lesser — like some other Obama alums — went on to elected office. He served four terms in the Massachusetts state Senate and is now an attorney in private practice.

Another member of the original crew, Michael Blake, joined Obama’s campaign in early 2007 and was the Iowa deputy political director and constituency outreach director.

At the reunion, “We get to celebrate something that had never happened before, electing a Black man president,” said Blake, who was the highest-ranking Black staffer on the Obama Iowa caucus team.

Blake became associate director of public engagement and deputy associate director of the Obama White House Office of Intergovernmental Affairs. He worked on Obama’s 2012 reelection bid, served as vice chair of the Democratic National Committee and was a three-term New York state assemblyman. He now is CEO of his firm ATLAS Strategy Group.

At Friday’s main event, Obama will be interviewed by the Crooked Media and “Pod Save America” crew, his former aides Jon Favreau, Dan Pfeiffer, Tommy Vietor and Alyssa Mastromonaco. Michelle Obama will also speak alongside former Obama aides Jen Psaki and Kal Penn.

Psaki was a traveling press secretary on the Obama 2008 campaign plane who went on to have a variety of top roles in the Obama administration. She was later Biden’s first press secretary and is now an MSNBC host. Penn, an actor, left Hollywood for a stretch to serve in the Obama White House Office of Public Engagement.

There will also be a performance by Grammy-winning musician Jon Batiste, the subject of a documentary called “American Symphony” that was acquired in September by Obama’s Higher Ground production company.

Aside from Friday’s festivities at McCormick Place, there are at least 29 other events at venues around the city.

On Thursday, there will be reunions at various restaurants of the teams from the Obama East Wing; campaigns in Florida and Iowa; and major donors who were part of Obama’s national finance committee. The 2008 and 2012 campaign managers, David Plouffe and Jim Messina, are also hosting a party.

On Friday, staffers from the Colorado, Wisconsin, Georgia and Nevada campaigns have separate reunions, as do Commerce Department and Latino alums. The night will be capped off by three afterparties, including one for the 2008 and 2012 media teams.

The Saturday reunions include separate events for the West Side Chicago Organizing for Action group and for the Black, LGBTQ and digital teams alumni.

Josh Earnest, who started as Obama’s communications director in Iowa in 2008 and later served as the administration’s last press secretary, will attend events with his wife, Natalie Wyeth Earnest, a former Obama Treasury Department assistant secretary for public affairs.

Earnest, now United Airlines’ executive vice president for communications and advertising, said being in public service “is a searing experience, even in the best of times, and it wasn’t always the best of times in that period.

“You form some really strong personal relationships, and it will be really fun to reconnect with the people who had those shared experiences,” he said.