Mr. Obama is navigating a landscape in which he must fit his obvious relish for the celebrity lifestyle with an unwritten code of conduct for past chief executives, a world that is his for the taking yet tradition dictates he do so incrementally. It’s a political scene where players may covet his endorsement or desire his invisibility.
Mr. Obama enjoys tremendous post-presidential popularity within the Democratic Party’s rank and file, but he has not always followed the unwritten rules of the Presidents Club.
Rather than ride into the sunset, he still lives Washington, residing in the multimillion-dollar Kalorama neighborhood about 2 miles from the White House. He also has stayed in the limelight by taking expensive vacations with celebrities, attending major sports events, visiting charities and, most important, campaigning for fellow Democrats in the 2018 midterm elections.
While there is no Emily Post for onetime leaders of the free world, former presidents typically do not thrust themselves so publicly into elections just two years after leaving office, historians say.
They also avoid criticism of their successors. President George W. Bush never voiced his opinions on the policies of the Obama administration that followed his.
“I’d say especially when you put him in comparison with the other invective that gets thrown around, some from his own people, he’s been surprisingly restrained,” said Allen C. Guelzo, an American history professor at Gettysburg College. “Tactful, even.”
The Obama endorsement
Mr. Obama’s popularity within the party and the political advocacy groups that surround him means his endorsement in the crowded field of presidential candidates would be a sought-after bouquet, although some of those close to him note he has carefully avoided picking any one Democrat when so many seek the party’s mantle.
“First of all, a former president can do whatever he wants,” said Ron Faucheux, a former Democratic elected official turned political analyst in Washington. “And I think at this time, among Democrats, an endorsement from Obama would be incredibly important.”
Yet as Mr. Faucheux and others noted, it’s unlikely an endorsement will be forthcoming.
“It isn’t appropriate,” longtime Washington analyst Charlie Cook said. “It isn’t done, unless it is someone in the family, like a son or brother.”
To the extent the next Democratic president will be continuing or building on Mr. Obama’s legacy, his former vice president, Joseph R. Biden, would seem to be the likely recipient of the coveted endorsement.
“I think every president objects to seeing their legacy dismantled,” Mr. Guelzo said. “President Trump is a major game changer on that front, and I imagine Obama has an acute anxiety about it all, as anyone would. All former presidents to some extent are bound to be zealous about preserving their legacy even if it was insubstantial.”
Not everyone believes Mr. Obama’s endorsement is necessary or would prove decisive, although it would certainly catapult a candidate lower in the polls.
“I think it might mean more if he endorsed someone other than Biden,” said one veteran Democratic presidential campaign consultant who has not gone with a candidate this time and asked to speak on background.
“It’s a delicate dance for him because this is a strange time. We’ve never had this many people running for president who you can say are legitimate candidates,” the consultant said. “But I’m not sure [an endorsement] matters that much, really. I don’t think it will matter much in the general election because Obama’s popularity doesn’t extend much beyond the already committed Democrats.”
In addition to tradition, a primary endorsement from Mr. Obama would be surprising. Some Democrats think Mr. Biden decided against running for president in 2016 partly because Mr. Obama did not offer his enthusiastic backing.
Mr. Obama’s office declined to comment on the 2020 race, but some careful observations have been offered privately.
“He believes that a robust primary in 2007 and 2008 not only made him a better general election candidate, but a better president, too,” said a person familiar with Mr. Obama’s current thinking. “And because of that, it’s unlikely that he will throw his support behind a specific candidate this early in the process.”
On the other hand, Mr. Obama has every intention of campaigning vigorously for many Democratic candidates in 2020, according to his staff. He intends to endorse, fundraise and hit the trail on behalf of congressional and gubernatorial candidates, as he did in Virginia and New Jersey, as well as helping the eventual presidential nominee.
Presidential endorsements of running mates haven’t always been smooth. Neither Dwight D. Eisenhower nor Ronald Reagan was seen as an enthusiastic backer of Richard Nixon or George H.W. Bush, respectively, and Al Gore drew criticism for supposedly keeping Bill Clinton at arm’s length when he sought the presidency in 2000.
Back in the high life again
Outside of the political realm, Mr. Obama has enjoyed life after the White House. While president, he declared that “at some point you’ve made enough money,” but that “point” appears to remain elusive for him more than two years out of office.
Last year, Mr. Obama expressed surprise at “how much money I got” in a speech in South Africa, but he insisted again there must be a limit.
“There’s only so much you can eat,” he said with a grin, according to contemporaneous accounts. “There’s only so big a house you can have. There’s only so many nice trips you can take.”
He has cavorted on the world’s most glamorous playgrounds with movie stars and business moguls. In the British Virgin Islands, where he was a guest of billionaire Richard Branson, and at an exclusive South Pacific resort, on an atoll near Tahiti, where Mr. Obama relaxed in a private villa not far from those of Bruce Springsteen and Meryl Streep.
He recently attended an NBA Finals game in Toronto, where the crowd gave him a rapturous welcome.
His family is thriving, too. His two daughters go to the finest schools. Malia attends Harvard University, and Sasha just graduated from the exclusive Sidwell Friends School in Washington. Wife Michelle’s “Becoming” memoir was the best-selling hardcover book of 2018 and sold a remarkable 10 million copies as of March, according to trade figures.
Still, for Mr. Obama, navigating lucrative post-presidential opportunities can be tricky. For those who hector the world about income inequality, living the lifestyle of the rich and famous can be problematic, and he has drawn his share of criticism from fellow liberals.
Some of their objections are rooted in the investment banking source of his lucre because speeches to Wall Street firms and investors have been a big part of it.
Mr. Obama has given at least nine speeches to Cantor Fitzgerald and other high-powered companies, and he has done so at $400,000 a pop, according to accounts.
He can command even greater fees abroad. Last week, Mr. Obama was reported to be receiving nearly $600,000 for a talk in Colombia.
Some of his longtime allies have been critical of Mr. Obama’s speaking riches.
At Vox, Matthew Yglesias said the Wall Street talks “undermined everything he believes in,” and usually adulatory outlets such as The Washington Post called it “a bad idea.”
Mr. Obama’s private staff declined to discuss his finances. They would neither confirm nor deny reported speaking fees and would not disclose how much money was involved in business deals of Mr. Obama and his wife.
The Obamas’ company Higher Ground signed a multiyear deal in 2018 with Netflix to produce vaguely defined content “to foster new, diverse voices in the entertainment biz,” as Variety described it. A similar multiyear deal for podcasts on Spotify was signed this month.
In the publishing world, too, the Obamas have brought in unprecedented numbers. The couple signed a $65 million deal with Penguin Random House for their political memoirs, and company executives have indicated they are pleased with the returns.
Mrs. Obama’s memoir may have garnered subtle criticism when her husband knocked it as ghostwritten, but it has been a huge bestseller. Thomas Rabe, chief executive of German media group Bertelsmann, in November called it the “most notable creative success of the last year” for the company’s publishing arm. He credited the memoir with a healthy contribution to the house’s 2.8% surge in revenue.
A publishing date for Mr. Obama’s memoir has not been set, and it is unlikely to be released this year.
Mr. Obama’s post-presidency appears to be on track with that enjoyed by Bill Clinton, the only other two-term Democratic president in the post-World War II era. In his first years out of office, Mr. Clinton gave multiple speeches for six-figure paydays, hauling in roughly $30 million from 2001 to 2005, according to financial statements wife Hillary filed as a U.S. senator at the time.
At times, such as the $500,000 Mr. Clinton received for one 2010 speech in Moscow, his post-presidential engagements raised eyebrows but they remained lucrative: Between January 2001, when he left office, and January 2013, Mr. Clinton’s fees from more than 500 speeches raked in an estimated $104 million, according to published reports.
Chicago’s South Side center
From a legal standpoint, the most troublesome project for Mr. Obama has been the $500 million Obama Presidential Center, slated to be built in Jackson Park on Chicago’s South Side, just below the University of Chicago campus.
The idea behind making “a difference in their communities” has always been a cornerstone of Mr. Obama’s political formulations and of his foundation, yet the project has become ensnared in fights with community activists and others.
Some Jackson Park supporters and community activists objected to the high-handed and unusual maneuvers by the City Council and the Illinois legislature to push the project forward, as well as the enormous footprint the planned four-building center will occupy on currently open public space.
An Obama appointee to the federal district court last week tossed a lawsuit against the project filed by Protect Our Parks and ruled that construction on the center could begin immediately.
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