Democrats ignored him.
And now, the prospects for the Trans-Pacific Partnership, the biggest free trade deal in history, to be finalized and adopted are grim -- unless Democrats can be convinced to change their minds or Republicans can find another way to revive the bills and rescue Obama's biggest second-term legislative priority.
The House overwhelmingly rejected the first in a series of trade bills Friday, with Democrats voting against a program that aids displaced workers -- in large part because, under the chamber's procedures, its defeat meant the vote on the so-called "fast track" bill that followed was only symbolic, so the measure couldn't be sent to Obama's desk.
In a statement released Friday afternoon, Obama praised the approval of the fast-track bill and continued to press for passage of the Trans-Pacific Partnership.
"These kinds of agreements make sure that the global economy's rules aren't written by countries like China; they're written by the United States of America," Obama said. "And to stand in their way is to do nothing but preserve the long-term status quo for American workers, and make it even harder for them to succeed."
But Friday's votes provided the clearest evidence yet that, with 19 months left in his presidency, Obama's pulpit is less bully than it's ever been before.
It also showcased the strength of populist elements of both parties, who beat back an intense lobbying push from traditional Washington forces like the Chamber of Commerce and the National Association of Manufacturers.
Friday's vote doesn't mean the package of trade bills are dead. House Republican leaders have called for re-votes by Tuesday, and noted that they could even delay those votes further if necessary, buying Obama a little more time to lobby his own party and GOP leaders time to twist arms.
In fact, the most controversial element of the package -- trade promotion authority, which allows Obama to submit deals like the 12-country Trans-Pacific Partnership to Congress for a vote without amendments, which trade negotiators say is crucial to finalizing the deal -- actually narrowly passed.
That vote, though, was meaningless because of House procedural rules that said a separate bill that included Trade Adjustment Assistance -- a program that helps workers who lose their jobs due to trade shifts, and that's typically favored by Democrats -- also had to pass, but it was defeated, 302-126.
But the prospect of a re-vote gave the White House reason for optimism on Friday.
White House Press Secretary Josh Earnest termed the trade failure a "procedural snafu," adding that it still reflected a success that lawmakers were able to pass promotion authority.
Earnest called Obama's visit with House Democrats on Friday "productive" and said the President would continue working with lawmakers to advance his trade agenda.
The Pelosi factor
It was House Minority Leader Nancy Pelosi, the California Democrat who shepherded some of Obama's most controversial first-term bills like health care reform into law, who hurt the President the most on Friday.
After staying on the sidelines for most of the trade fight, Pelosi took to the House floor and announced her opposition to the bill -- giving cover to other Democrats who were considering breaking with Obama.
She acknowledged the strangeness of Democrats rejecting a Trade Adjustment Assistance measure they've favored for decades, but said the purpose was to win a broader fight.
"Our people would rather have a job than trade assistance," Pelosi said. "Its defeat, sad to say, is the only way that we will be able to slow down the fast track."
With Pelosi's opposition and Hillary Clinton, the Democratic front-runner in the 2016 presidential race, also keeping mum on trade promotion authority, Obama had scant high-level support within his own ranks.
Obama unable to sway Democrats
The President attended a 9:30 a.m. gathering of House Democrats, making his case after several high-level officials -- including Labor Secretary Tom Perez and White House Chief of Staff Denis McDonough -- made their cases in the days leading up to the vote.
As he left the meeting, Obama said, "I don't think you ever nail anything down around here. It's always moving."
Democrats who attended said they weren't swayed and that the President's outreach came too late.
"The President tried to both guilt people and impugn their integrity. I was insulted," Rep. Peter Defazio, D-Oregon, told reporters after the meeting.
One House Democrat told CNN on the condition of anonymity that in Friday's meeting, Obama "was fine until he turned it at the end and became indignant and alienated some folks. Bottom line, he may have swayed some Ds to vote yes, but Pelosi sealed the deal to vote no."
Another House Democrat said Obama's last-minute lobbying effort "absolutely" hurt the bill's chances.
"Democrats believe they often are taken granted and not appreciated," this House Democrat said. "There was a very strong concern about the lost jobs and growing income inequality. Unions are the last line of defense. A number of reporters have asked whether Democrats felt threatened by the unions. Most told me that they wanted to do nothing to further weaken unions."
Added this member of Congress, pointedly: "Ms. Clinton should take notice."
Republicans pushed hard for the trade package, but indicated it would largely be up to Obama to convince Democrats to change their mind on the Trade Adjustment Assistance portion of the set of bills.
House Speaker John Boehner called Friday's rejection of that bill "disappointing."
"Republicans did our part, and we remain committed to free trade because it is critical to creating jobs and growing our economy," he said. "I'm pleased that a bipartisan House majority supported trade promotion authority. This is an opportunity for the Democratic Party to take stock and move forward in a constructive fashion on behalf of the American people."
The next steps
Going into the weekend, it was unclear what exactly could change over the weekend to lead to a different result early next week, and which, if any, Democrats would vote differently if the TAA portion of the bill were to be reconsidered.
Pelosi already had her demands in mind. In a letter to House Democrats, she said the prospects for trade promotion authority would "greatly increase with the passage of a robust highway bill."
Other Democrats made the case that Democrats might realize their gambit could result in the elimination of the Trade Adjustment Assistance program after the symbolic vote in favor of trade promotion authority -- the bill Democrats really want to kill.
"If members of my caucus come to the belief that ... you could end up getting fast track without Trade Adjustment Assistance, I think many of my colleagues would reconsider Trade Adjustment Assistance," New York Democratic Rep. Steve Israel said. But, he added, "I don't think anybody knows where we're going right now.
Wisconsin Republican Rep. Paul Ryan, the point person for House Republicans on trade, told reporters after Friday's votes, "this isn't over yet."
"America is being watched by the rest of world," Ryan warned, adding, "now the President has some work yet to do with his party to complete this process."