Returning to Springfield, Illinois, site of his presidential campaign launch nine years ago, 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.
Obama reflected on his time in the Illinois state Senate when he worked with Republicans, even on issues where they didn't agree with. He contrasted that with current political rhetoric, saying in the state Senate they didn't refer to name calling.
"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."
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. And White House aides argue it is Republicans, not Obama, who have prevented meaningful legislative action for much of the past several years.
But no matter where the blame falls, the situation in Washington is a distant cry from the promise of reconciliation that Obama delivered on a frozen morning in Springfield.
Standing before a crowd of thousands that had gathered at the Old State Capitol building, Obama cited in 2007, "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 conceded in January.
"It's one of the few regrets of my presidency -- that the rancor and suspicion between the parties has gotten worse instead of better," Obama said during his State of the Union address. "I have no doubt a president with the gifts of Lincoln or Roosevelt might have better bridged the divide, and I guarantee I'll keep trying to be better so long as I hold this office."
In a speech to Illinois state lawmakers on Wednesday, Obama plans to detail "what we can do together as a country to build a better politics, and one that reflects our better selves," according to White House spokesman Josh Earnest.
The White House said Obama would also address, "without endorsing a specific path forward," how to combat gerrymandering -- the process of redrawing congressional districts to ensure a particular political outcome.
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.
CNN's Allie Malloy contributed to this report.