As they watched police in military gear spread tear gas in a St. Louis suburb in recent days, White House aides knew President Obama would be expected to weigh in on race.
But rather than bold words, Obama's reaction in this case has been shaped by an acute awareness of self-imposed limits.
White House officials argued that in a nation polarized on racial issues — and deeply split about the president — strong language from Obama about the shooting of 18-year-old Michael Brown and the protests and looting in Ferguson, Mo., would risk worsening the problem rather than making it better.
"His words can't heal things overnight — centuries of racial history and decades of economic unwinding take time to repair. But if his words are careless, they can inflame the situation, and he knows that," said one senior aide, speaking anonymously to discuss the president's thinking.
As a result, Obama has not offered another "Trayvon Martin moment" of empathy with a young black man who some people believe was the victim of racial prejudice.
Instead, in a brief news conference at the White House on Monday, Obama offered carefully balanced statements about the need to ensure the rights of peaceful protest, but also to combat criminal behavior.
"We've got to make sure that we are able to distinguish between peaceful protesters who may have some legitimate grievances and maybe long-standing grievances, and those who are using this tragic death as an excuse to engage in criminal behavior," he said.
The closest Obama came to personal reflection was when he talked about sending in federal investigators and defended his decision not to go to Ferguson himself.
"I have to be very careful about not prejudging these events before investigations are completed because ... the DOJ works for me," Obama said, referring to the Justice Department. "When they're conducting an investigation, I've got to make sure that I don't look like I'm putting my thumb on the scales one way or the other."
The White House reaction has been shaped less by the Martin case than by another racially charged incident from early in his presidency — the firing of Shirley Sherrod — that many Americans have probably forgotten.
Administration officials forced Sherrod, a black Agriculture Department official, to resign in 2010 after she was accused — falsely, as it turned out — of making anti-white comments. White House aides pushed to quickly remove her in a botched attempt to get ahead of a media controversy.
Sherrod's story has become a cautionary tale in the White House about the dangers of reacting too quickly to a racially charged situation.
White House officials say the president has, over time, become mindful of getting caught up in the swirl of a media storm — even those that carry personal resonance.
Some of his political allies endorse the reticence.
"He really has said as much as probably he should," said Congressional Black Caucus Chairwoman Rep. Marcia L. Fudge (D-Ohio). "I know there are a lot of people who want him to be much stronger, but the reality is, we really live in two Americas."
Rather than using the president's personal story to address the unrest in Ferguson, aides worked back channels to communicate with the African American community. The president received regular briefings from Atty. Gen. Eric H. Holder Jr., and Obama announced Monday that he was sending Holder to Ferguson on Wednesday.
Obama has won strong marks from civil rights leaders for the Justice Department's investigation and the rare decision to conduct a separate autopsy. Those moves sent strong signals that the administration would not be leaving the case to local authorities, said NAACP President Cornell William Brooks.
Given the unrest in Ferguson, Obama has had to be more cautious so as not to inflame tension, Brooks said.
"But his actions speak volumes," Brooks said. "The prose of his conduct and decisions outweigh the poetry of any press release."
Although Obama is reluctant to dive into racial controversies, in his second term he has shown a willingness to speak at length and in personal terms about his experience with prejudice. He has given more attention to programs targeting young black men, and he has spoken more bluntly about the gun violence and economic inequality that disproportionately affect black communities.
That was notably true in the Martin case, in which Obama called a small team to his office a few days after George Zimmerman was acquitted of shooting Martin and said it was time for him to address the nation.
"Trayvon Martin could have been me 35 years ago," he said, in what became the headline quote from his remarks.
Obama also crafted Monday's much less emotional comments mostly without the help of his speechwriting staff, officials said.
"I've said this before, in too many communities around the country, a gulf of mistrust exists between local residents and law enforcement," Obama said. "In too many communities, too many young men of color are left behind and seen only as objects of fear."
But before the Martin remarks, there were mistakes, White House aides acknowledge.
Five years after it happened, advisors this week were still thinking about the swift, harsh reaction that followed Obama's off-the-cuff remarks about the arrest of black scholar Henry Louis Gates Jr. in 2009. Although Obama's remarks were wide-ranging, what lingered was his quote that police had "acted stupidly."
His attempt to make up for the stumble with the awkward and gimmicky White House "beer summit" with Vice President Joe Biden, Gates and the officer who made the arrest was not a high point in race — or public — relations.
"Go back to the beer summit. Go back to the comment that he made about Trayvon. How much grief did he take for that?" Fudge said. "At some point you say, 'I don't want to be the person who divides this nation. I want to bring us together. That is what the role of the president is.'"
Just as prominent in his mind as Martin, one advisor said, is the memory of Sherrod, who was pushed from her job over supposedly anti-white remarks she made to a black audience.
After listening to her full speech, however, administration officials decided Sherrod's words had been taken out of context and misrepresented by conservative critics. The administration apologized to her for the firing and offered her a new position. That experience warned them against getting disoriented by the media storm itself.
Obama has made it known that he wants to be "open and clear about his feelings on the subject" when he speaks publicly about Ferguson, but that he didn't want to prejudice the situation, senior advisor Valerie Jarrett said.
Like the rest of the president's staff, she said, she's trying to follow his lead in not giving in to a "gut reaction" to the events surrounding Brown's death in Ferguson.
"I have to have a reaction based on the facts," Jarrett said. "We all do."
Parsons reported from Edgartown and Hennessey from Washington.