Brent Rosenberg was an early and enthusiastic Barack Obama supporter at a place and time when it mattered most: Iowa 2008, in the run-up to the first-in-the-nation presidential-nominating contest.
"I worked hard during the caucuses," said Rosenberg, a Des Moines lawyer and lifelong Democrat. "I led all my friends and relatives to him."
So it's with evident pain that he now speaks about the president, on the eve of Obama's speech on military action against Syria, with disappointment, if not regret.
"This has been a squandering of a historic opportunity," Rosenberg said, referring to the promise he believed Obama — whose road to the White House was paved by those 2008 Iowa caucuses — brought with him to the presidency.
His discontent embodies perhaps the biggest complication the president faces Tuesday night: Obama's toughest, most skeptical audience is stocked with once-ardent supporters struggling to reconcile the man they see presiding over the weekslong, herky-jerky move to military action, with the young anti-war senator they worked tirelessly to put in office.
One of Obama's strongest allies, MoveOn.org, has gone so far as to campaign against the president's plan. On Monday, the big progressive organization launched its latest stay-out-of-Syria salvo, a television ad that urges members of Congress to vote no on the administration's call for military action.
Taking on Obama so directly hasn't been easy for MoveOn.org.
"Our members do not relish opposing the president," says Executive Director Anna Galland. "They worked their hearts out for him — including an early endorsement in 2008."
"It's with sadness, respect and resolve that we are saying no to military action," she says.
Even some Democrats who say they would have supported quick military action in Syria, without congressional approval, view the unfolding drama as eroding the president's standing and undermining the party's ability to move forward on the debt ceiling, immigration and Obamacare this fall.
"Watching all this from afar, it has looked very untidy," says Garry South, a California-based Democratic strategist. "I get a sinking feeling in the pit of my stomach; it's been a very bad first nine months of the second term."
Disenchanted, But For Different Reasons
What South says has surprised him is that the president's wavering path to Syria has seemed out of sync with his previous military and foreign policy decisions — including the 2011 raid that led to the capture and killing of Osama bin Laden.
"He has shown as commander in chief a surprising amount of decisiveness for someone who is a pretty liberal Democrat," South said. "That's why I don't understand what I'm seeing here — someone rife with indecision."
"It bothers me, as a Democrat, if I'm for a Syrian strike or not," he said. "An American president cannot look weak. If this were a President Reagan or Clinton, these strikes would have already been over and the speech would be about what just happened, not what's going to happen."
Rosenberg agrees with South's assessment that the president has been weakened by the drawn-out debate. He argues that Syria, and other Middle East conflicts, present presidents with "historically unresolvable" dilemmas.
"Syria, in my mind, is a quagmire and it's a mistake to think there is a right answer," he said. "There isn't."
"A stronger president could have gotten through this without a lot of carnage, and, now, I'm not sure he can," Rosenberg says. "It struck me as problematic that all of a sudden he pulled up after the British Parliament said no, and then kicked it to Congress — that looked very weak."
Galland, the MoveOn.org leader, says it's her hope Congress won't approve Syrian military intervention, and the president "will use other levers at his disposal to respond to the horrific reports of chemical weapons in Syria."
Those levers? Diplomacy and humanitarian aide, she said, "nonviolent alternatives."
Complicating The Agenda
Galland insists that her members' opposition to the president's Syrian plan won't affect their commitment to working for the full implementation of Obamacare or, for example, supporting the president's clean air goals.
"I don't think our members are going to say they're going to oppose Obamacare because of military strikes," she said.
That said, Galland and other Democrats say they are deeply concerned about the broader political environment, and the deleterious effect this national and intraparty debate on Syria will have for the president's agenda.
"If he wins on this vote, we'll be launching military strikes against Syria that the progressive base opposes," she said. "And if he loses the vote, I worry that political commentators will see him as weakened."
It's not an irrational worry.
"The president loses a gun control fight in Congress," said South. "Immigration reform has gone nowhere in the House, and now he goes back to the same Congress that wouldn't give him anything?"
"It just doesn't make any sense to me," he said.
South argues that Obama has to launch a Syrian strike, however, even if Congress doesn't approve.
"The toothpaste is out of the tube; he has to do something," South said. "If not, he looks like a paper tiger, and that's not only bad for the U.S., that's bad for the world."
As the administration continues to monitor a Russian proposal to have international monitors take control of Syrian chemical weapons in an effort to avoid a military strike, some Democrats characterized it as the best opportunity for Obama to salvage a bad situation.
"If the president is smart he will get down on his knees and thank Mr. Putin who, in the process of reasserting Russian power in the Middle East, has given Mr. Obama a way to get through this episode intact," said California-based Democratic strategist and lawyer Darry Sragow. "The best outcome: Congress grants the president the ability to intervene, he doesn't use it, giving time for peaceful initiatives work, and they do."
In any case, few of the president's supporters go so far as to say they regret voting for him in 2008 or in 2012.
"I can only look back at what my choices were in 2008, and in 2012, and think they were the right choices," Rosenberg, the Iowa lawyer, said.
But he worries that the Syria muddle's damage could be lasting — perhaps even extending to the 2016 presidential election and damaging Hillary Clinton, the Democrat he sees emerging as the nominee and one he would support.