Returning to Springfield, Illinois, the site of his presidential campaign launch nine years ago to the day, Obama confronted the gaping shortfall between his lofty 2007 rhetoric on changing the country's political discourse, and the reality of politics today: meaner and more divided than ever.
Without delving into specifics about the increasingly nasty campaign to replace him, Obama warned against yielding politics to the loudest or angriest voices.
Describing a "poisonous political climate that pushes people away from participating in our public life," Obama appealed for civility in government.
"It turns folks off. It discourages them. Makes them cynical. And when that happens, more powerful and extreme voices fill the void," he said.
Obama didn't accept responsibility for the rancorous language that has infected the 2016 campaign trail -- including Donald Trump's vulgar descriptions of his Republican opponents this week. But he did concede the country's political environment has only turned more toxic over his two terms in office.
"We've got to build a better politics, one that's less of a spectacle and more of a battle of ideas, one that's less of a business and more of a mission," Obama said, admitted later that "the tone of our politics hasn't gotten better since I was inaugurated. In fact it's gotten worse."
"I still believe in politics of hope," Obama declared. "Choosing that kind of politics, sustained over the tranquil and steady dedication of a lifetime, that's something that remains entirely up to us."
The message was broadly the same as his announcement speech in 2007, when, standing before a crowd of thousands that had gathered at the Old State Capitol building, Obama cited "the smallness of our politics" and decried "the ease with which we're distracted by the petty and trivial, our chronic avoidance of tough decisions, our preference for scoring cheap political points instead of rolling up our sleeves and building a working consensus to tackle big problems."
Nine years later, that description of the country's governing environment remains largely intact, despite Obama's pledges in his subsequent campaign to move beyond the old ways of Washington.
A budget agreement this year, hailed as an example of bipartisanship at work, was notable mostly for its avoidance of a government shutdown -- a consequence of fiscal battles that seemed impossible before 2013, when the government actually did shutdown for two weeks amid a budget stalemate.
Big-ticket legislative items like comprehensive immigration reform and tax code reform have gone by the wayside, mired in partisan arguments that Obama has shown little ability to mitigate.
And an appetite for scoring "cheap political points" has only grown more insatiable in an era of quick-hit social media attacks.
There are vows Obama delivered in Springfield that have gotten closer to becoming reality.
His health care law brought the country's uninsured rate to record lows, though not nearly to the "universal health care" he insisted upon. His pledge to break the country from the "tyranny of oil" has inched forward though investments in clean energy. And his promise to end the Iraq war materialized, though terrorist gains after U.S. combat troops left have forced Obama to send Special Forces back into the country.
That progress aside, Obama's determination to change "the ways of Washington" has shown few signs of being realized -- a fact Obama acknowledged Wednesday.
"One of my few regrets is my inability to reduce the polarization and meanness in our politics," Obama said. "I was able to be part of that here, and yet couldn't translate it the way I wanted into our politics in Washington."
He referred to himself in the remarks as a "progressive" Democrat, a pointed term that's definition has been up for debate among Democratic presidential candidates Hillary Clinton and Bernie Sanders.
He used his remarks to highlight concrete ways the political system can change, including making it easier for people to vote and insisting upon civility in political discourse.
And he called for an end to the practice of gerrymandering -- the redefining of congressional districts to favor one party.
"We should change the way our districts are drawn. In America, politicians should not pick their voters. Voters should pick their politicians," he said, without making any specific calls for changes in electoral regulations.
Contrasting the current political environment with his own time in the Illinois state Senate, Obama recalled working with Republicans even on issues where they didn't agree.
"They trusted each other even if they didn't agree," Obama said. "We didn't call each other idiots or fascists who were trying to destroy America."
Even in the Illinois state capital, though, things seem to have only gotten worse since Obama left. In his 2007 speech, Obama described a place with the opposite ideals of Washington, where he "learned to disagree without being disagreeable."
Today, the state's lawmakers are locked in a bitter fight over spending that has led to credit downgrades and the longest streak without a budget in state history.
For Obama, a return to Springfield comes imbued with nostalgia for his earliest days in the national spotlight. His 2007 address launched a long-shot path to the White House which cut through a field of seasoned contenders, including Hillary Clinton.
Even as he delivered the speech, members of Clinton's campaign had already begun questioning his experience and readiness for the top job. He also faced persistent questions about the nation's willingness to elevate an African-American as a major party presidential nominee, let alone commander-in-chief.
Those questions were put to rest months later when Obama bested Clinton for the party's nomination, and beat Sen. John McCain by a decisive margin in the general election.
But at the time of Obama's announcement, his candidacy offered only the potential for historic change in the country.
Obama, in his announcement address, evoked the memory of Abraham Lincoln, who began his political career in the same location. And he recognized the unlikely nature of his presidential bid.
"I recognize there is a certain presumptuousness in this -- a certain audacity -- to this announcement," Obama said then, with his wife, Michelle, and two young daughters standing nearby. "I know that I haven't spent a lot of time learning the ways of Washington, but I've been there long enough to know that."
"People who love their country can change it," he said.