Barack Obama and his aides expected to take on President Donald Trump at some point, but they didn’t think it would happen this quickly.

Now they’re trying to find the right balance on issues that demand a response, and how to use Obama to deliver the selective pushback. Obama and his team are monitoring what’s happening at the White House, and not ruling out the possibility that Obama will challenge Trump more forcefully in the coming months, according to people who’ve been in contact with the former president.


It depends on Trump. It also depends, the people close to the former president said Monday, on whether speaking out would just set him up to have no effect and be dismissed, and result in empowering Trump more, which is a very real worry for them.

From his vacation spot in the Caribbean, Obama has been keeping up with news from Washington and the protests around the country. Friends and former aides have been emailing and talking to him. His staff at his post-presidential office, still unpacking its boxes, told him about the reporters who kept asking, even in Trump’s first week as president, whether enough had happened already to meet his threshold to speak up.

He decided he finally had to say something about the immigration executive order that’s sparked outrage across the country. But he decided he couldn’t say it himself—not yet, at least.

The result was an extraordinary statement Monday from an Obama spokesperson that “President Obama is heartened by the level of engagement taking place in communities around the country.”

But Obama won’t weigh in on Trump’s firing deputy attorney general Sally Yates for refusing to enforce the executive order that sparked the statement, wary of getting drawn in to every battle.

Democrats are desperate for leadership, but some fear the battle could become all about him. There are frustrations over Obama’s handling of the party, and how he insisted on a low-drama transfer of power.

Rep. Ted Lieu (D-Calif.) took a long pause when asked if he’d want to see Obama out more forcefully.

“I wouldn’t be opposed if he spoke out,” Lieu said. “I just don’t know what effect it would be.”

Rep. Ted Lieu: “In hindsight, I believe it was wrong for Barack Obama to normalize Donald Trump.” | AP Photo

“In hindsight, I believe it was wrong for Barack Obama to normalize Donald Trump,” Lieu added.

Lieu isn’t the only one with hesitations. Several Democratic officials passed on the chance to say if Obama’s decision to wade in was a positive.

By focusing in the statement Monday on the efforts of protesters, Obama tried to draw a connection to the call to action to his supporters in his farewell address three weeks ago in Chicago. By including a line that “American values are at stake,” Obama issued a reminder of what would pull him in more.

What they don’t want, though, is for Obama to become the face of the anti-Trump movement.

"The only way that our values get reinstated is if people take this responsibility on themselves,” said Eric Schultz, a former White House aide who’s serving as a senior adviser to the former president’s office.

Obama knows there are many much more drastic measures that he might want to speak out on, and he’s saving more direct intervention for maximum impact, people familiar with his thinking say. He knows he only gets one chance at it being the first time that he takes on Trump himself.

“He’ll know the right time,” said one person involved. “He will have the best sense of when he needs to do it directly.”

That means there won’t be a statement from Obama on Trump’s Supreme Court pick, or on other more standard issues of the political fray, with the former president continuing to be concerned both about sticking to the tradition of giving deference to successors and worried that being too active will keep a new generation of Democrats from rising up.

California Attorney General Xavier Becerra said he shared the concerns that Obama becomes the face of the opposition or makes it seem purely partisan.

“At the end of the day we have to have an all-hands-on-deck policy here to deal with this moving target,” Lieu said, but “I would welcome and acknowledge and accept whatever President Obama decides to do.”

Obama’s closest aides, though, have been speaking up with increasing force.

“Trump is succeeding in uniting the country — against him. Above all, he cares about his popularity. Will his yes men ever challenge him?” wrote Obama’s friend and former Education secretary, Arne Duncan.

Using Twitter so that they can get their thoughts out in a completely controlled way, they’ve hit him on the immigration executive order, the White House statement for Holocaust Remembrance Day that purposefully left out mention of the six million Jews killed and the reorganization of the National Security Council to elevate Trump chief strategist Steve Bannon.

Susan Rice, Obama’s former national security adviser, called the NSC move “stone cold crazy,” wondered about “what sickness enables” the Holocaust statement without the reference to the Jews and called the refugee order “nuts.”

Ben Rhodes, the former deputy national security adviser and now serving as a foreign policy adviser to Obama in his post presidency, slammed Trump and his White House for comparing Friday’s executive order to actions Obama took in 2011 to add screening to Iraqis after learning of a direct threat.

“This is a lie,” Rhodes wrote. “There was no ban on Iraqis in 2011. Anyone pushing that line is hiding behind a lie because they can't defend the EO.” In another tweet, Rhodes added that Trump is doing “precisely what Obama argued against over and over and over again in 2015-2016.”

“I immigrated to US as 9yo & became UN ambass; other diplomats marveled @familiar American story. Now they're horrified by unAmerican madness,” wrote Samantha Power, Obama’s former ambassador to the United Nations.

Another common question posed by former Obama aides: How would Republicans have reacted if Obama had done what Trump had, such as issue a Holocaust Remembrance Day statement that doesn’t specifically mention Jews?

“Just imagine the response if Pres. Obama did that,” Rice wrote.

“If Obama omitted the Jewish people from a statement on the Holocaust are we really supposed to believe the RNC wouldn't have been critical?” Rhodes wrote.

Monday night, former Attorney General Eric Holder, another friend of Obama's, spoke up for Yates.

"For standing up for what is right," read the text over the photo of her he tweeted, "#THANKYOUSALLY."