If President Barack Obama’s year ended in November, it would have been one of the worst of his presidency.

Good thing he had the past five weeks.


Obama feels liberated, aides say, and sees the recent flurry of aggressive executive action and deal-making as a pivot for him to spend his final two years in office being more the president he always wanted to be.

As of Wednesday, that includes doing what 50-plus years of predecessors couldn’t do in relations with Cuba, propelling a generational shift in American foreign policy that could bring down a final remaining pillar of the Cold War. The Cuba announcement follows a post-Election Day sprint that included sealing a landmark climate agreement with China, shielding 5 million undocumented immigrants from deportation, and reaching a deal that funds most of the government for nearly a year while protecting Obamacare and other top priorities.

The midterms are done, and Obama feels that he doesn’t have to worry about being the driving factor in any other Democrat’s election. He has spent a year nudging Americans to judge him less on legislative accomplishments and more on his executive actions. And now he has a fully Republican Congress that he can alternate butting up against and making deals with — but really not thinking much about it at all.

( Also on POLITICO: The Democrats' risky Cuba bet)

“We were trapped in this debate of: ‘Is Obama helping or hurting?,’ ‘Was it a mistake to say his policies were on the ballot, or was it the right thing to do?’” a senior Obama aide said this week as the final details of American Alan Gross’ release from a Cuban prison — which enabled the deal with the island country — were being worked out. “We are more the masters of our own destiny than we were before.”

Republicans believe Obama is either delusional or in denial about the brutal election results for Democrats. But the White House started preparing for the post-election sprint well before November.

As they headed into the final weeks before the midterms that they always knew would be rough, the mood in the West Wing was dark. But, the Obama aide said, Obama and his staff were already plotting “how we were going to win the period between the midterms and the end of the year.”

Months before the election, chief of staff Denis McDonough pushed for the president’s mid-November China trip as a chance to reset — provided they could deliver some accomplishments, unlike the one that Obama took through South Korea, right after the 2010 shellacking, when a planned trade deal fell through. For weeks, McDonough had been calling in outside advisers and Cabinet secretaries, putting together ideas for a State of the Union that was already in the early stages (though aides don’t expect a full first draft to be done until the president gets back from his Hawaii vacation).

While last year, senior Obama adviser Dan Pfeiffer spent late December hammering out a memo mapping how to reset after the 2013 lost year, there’s no memo planned this time. They think the reset’s already underway.

Obama’s always ready to make a deal, often at the expense of brushing off his base — just look at what happened with the omnibus spending plan less than a week ago. But he and his aides were boxed in by his promise to move on immigration reform by the end of the year. The choice: back off and lose the Democratic base or, the Obama aide said, “say ‘yes,’ which automatically puts you on this aggressive, ‘I’m not backing down approach.’”

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The next day, Obama gathered his National Security Council in the Situation Room to talk Cuba. Meanwhile, aides were preparing for the president’s endorsement of net neutrality, which the White House gloated over as a demonstration that he could still shape the conversation even with just a short statement and a fact sheet. The climate agreement was announced in China while people were still catching up on the net neutrality move.

Those weeks were nothing like the rolling disaster of the first 10 months of 2014, which included Russian President Vladimir Putin’s extended geopolitical flip-off; the long-haul bureaucratic bungling of veterans health care, exacerbated by a junior-varsity public relations response; being caught off-guard by the rise of the Islamic State of Iraq and the Levant, and hitting the golf course hours after the beheading of U.S. journalist James Foley; the spread of Ebola to the U.S. and the early bungled response; and an election cycle during which Democrats were competing to see who could slam Obama the hardest.

Yet at the end of it, Obama and his aides are focusing on the final chapter of 2014, believing the stumbles from earlier in the year will fade.

Obamacare enrollment is ticking up, the economy is on the longest job-growth streak since the 1990s, Obama’s done more on environmental protections than any previous president, and he took the single largest unilateral action on immigration policy in history.

And though they got nowhere on trying to persuade Congress to raise the minimum wage, Obama and his advisers tout the success of shaping the conversation in a way that prompted companies and a growing number of cities and states to raise wages on their own.

( Also on POLITICO: How GOP may nix Cuba play)

“This certainly has been our most productive year since the Republicans took over,” the Obama aide said, calling 2014, in the context of what happens in any presidency, “an excellent year.”

Republicans and even a number of Democrats in Washington tend to literally laugh at this, though they acknowledge that, since the midterms, Obama has been more aggressive — much to the dismay of some.

Sen. Rob Portman (R-Ohio), one of the leading voices for bipartisan outreach and one of the few Republican senators who has met privately with Obama over the course of the year, literally threw up his hands when told that’s the line coming out of the White House.

“If that’s what they want to believe, that’s fine. I just don’t see it,” Portman said.

“2014 wasn’t exactly a cakewalk,” said retiring Sen. Tom Harkin (D-Iowa), one of the Senate’s most reliable liberals.

“Could have been — it’s OK. I don’t think it’s great,” said Sen. Sherrod Brown (D-Ohio), looking back on Obama’s year. “It wasn’t terrible. But compared to what?”

Obama’s liberation, Republicans say, is a combination of delusion and bitter denial that’s just setting him up for a lot of pain once Congress is fully in their hands in two weeks.

“I wish he had accepted the results of the election and decided it was time maybe to go in a different direction. I don’t know that he got the message,” said Sen. John Thune (R-S.D.). “Coming out of the gate very early with his immigration decision wasn’t helpful.”

But when the president delivers his expected year-end news conference later this week, the breakthrough on Cuba will be the freshest, driving action.

That doesn’t mean reworking Cuba policy in Congress is going to be easy: As much as Obama will repeat his line Wednesday that he looks “forward to engaging Congress in an honest and serious debate about lifting the embargo,” resistance was mounted almost immediately, including from the White House’s top ally on immigration reform among House Republicans, Rep. Mario Diaz-Balart of Florida. Diaz-Balart called Obama Cuba’s “appeaser in chief,” and outgoing Senate Foreign Relations Committee Chairman Robert Menendez (D-N.J.) called the move a “dramatic and mistaken change of policy.”

( Also on POLITICO: Obama's December surprise)

But after a year of executive-action talk that succeeded mostly in making reporters groan at the mention of the phrase “pen and phone,” Obama demonstrated Wednesday just how far he thinks he can go. This Congress may never confirm an ambassador to Cuba for him, but Obama has instructed Secretary of State John Kerry to go about opening a U.S. Embassy in Havana, anyway.

Obama’s task will be trying to contain the political blowback to make sure that a Democrat holds the White House in 2016; if not, all of the steps he’s taking by executive action can be rolled back by the time the Inauguration bleachers are packed up at the Capitol in 2017. But he’s heading into 2015 without dwelling much on Congress.

The feeling is mutual, even among Democrats.

“You know, my experience in life is every year is, better than the last,” said Sen. Richard Blumenthal (D-Conn.), ducking away when asked if he’d rate Obama’s 2014 better than his 2013.

Asked for his own assessment of Obama’s 2014 the day before the Cuba news broke, Sen. Bill Nelson (D-Fla.) demurred.

“How can I answer that? I don’t know the answer. Let’s get through it first.”

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