Five questions for Obama’s presser

President Obama will hold his traditional holiday press conference on Friday, hours before he departs for a 17-day Hawaiian vacation. 

The press conference comes after a frantic lame-duck session for the president and just two days after he announced an historic effort to normalize relations with Cuba. 

{mosads}In recent days, Obama has also signed into law a $1.1 trillion government spending package that will keep most of the government funded through the remainder of the fiscal year. Plus, he’s had to assuage worries that North Korea launched a cyberattack against Sony Pictures Entertainment and grapple with indications the Russian economy is on the brink of collapse.

But for a White House that spent much of the year playing defense, recent events have given Obama a chance to accumulate some signature accomplishments.

“If you review the substantial accomplishments that we’ve racked up here, particularly in the last few weeks — from this historic climate deal with China, to finally taking action to address some of the broken aspects of our immigration system, to obviously the substantial historic announcement on Cuba — the president is pleased with the kind of progress that we have made,” press secretary Josh Earnest said Thursday.

Still, Obama’s likely to face some heat from the press before he escapes Washington. Here are five areas where the president is likely to face tough questioning:

1) Will the new Cuba policy embolden the Castro regime and worsen human rights abuses in the country? How will the White House defeat congressional efforts to roll back this policy change?

President Obama’s announcement Wednesday that he was easing travel and trade restrictions to Cuba and seeking to re-establish diplomatic ties was met with bipartisan furor on Capitol Hill. 

Lawmakers are already threatening to withhold funding for the establishment of an embassy and say they’ll work to block the confirmation of an ambassador. Some have said they’ll use the power of the purse to prevent the Treasury and Commerce departments from rolling out the new rules posed by the administration. 

The White House says it’s not concerned, but Obama could be pressed on how he plans to prevent the legislation from gaining traction — or if he can rally lawmakers to legislate a drawdown of the embargo policy.

And the president will also likely be asked to define some metrics to show how and when the new policy is working, if at all. While Obama argued in a speech on Wednesday the current policy had proven ineffective over five decades, many critics say the changes will only help prop up the Castro regime and worsen living conditions on the island.  

2) Was North Korea responsible for the cyberattack against Sony? Was the studio justified in pulling “The Interview” from theaters?

The White House said Thursday that an investigation into who was responsible for the massive data breach was “progressing,” reiterating that the president and top senior administration officials were treating the situation as a “legitimate national security matter.”

But Earnest declined to confirm reports that North Korea was responsible for the breach, only saying the administration was contemplating a “proportional response.”

Expect reporters to demand the president say whether he believes Pyongyang was behind the attack, whether China had a role, and what shape retaliatory efforts could take.

Neither has the White House said whether the president thought it was a good idea for Sony to pull the Seth Rogen comedy after someone claiming credit for the hack released a statement to news organizations warning of a 9/11-style attack against American moviegoers who went to see the film. 

3) How will the White House navigate the relationship with Capitol Hill as Republicans take control?

The president has never been known for his mastery of Capitol Hill negotiations, and his challenge will only intensify in the 2015.  

Obama is hopeful he can strike deals on trade and corporate tax reform with Republicans, but GOP leaders will be eager to use their newfound control to launch new investigations of the administration and pass legislation on issues dear to the president, such as healthcare and immigration. 

Even if Obama can strike a deal despite that rancor, he’ll then have to sell it to a Democratic leadership team that has demonstrated increased frustration with the White House.

During the debate over the “cromnibus,” Sen. Elizabeth Warren (D-Mass.) and House Minority Leader Nancy Pelosi (D-Calif.) railed against the bill, arguing it conceded too much to Republicans. Warren has also lobbied against the president’s nomination to fill a high-level Treasury post, and against giving him additional authority to pass trade deals.

Meanwhile, a spat between the White House and outgoing Senate Majority Leader Harry Reid’s (D-Nev.) chief of staff has spilled out into the public, and Reid blamed the administration for November’s electoral losses. 

Obama could be pressed on how he can keep Democrats united — an important point as he seeks leverage to negotiate — and repair relationships strained in recent years.  

4) What is the president’s biggest accomplishment or regret in 2014?  

President Obama arguably didn’t have the best 2014. For most of the year, he failed to get much accomplished in terms of legislation. He was constantly distracted by world events which took the wind out of his domestic agenda. To top it off, he saw Democrats lose the Senate under his watch.  

“He didn’t have the best year in the by and by,” said Democratic strategist Jim Manley.  

But Manley and other strategists give Obama credit for work he’s done since the midterm elections through executive actions, working with Congress to pass the budget and this week’s move to open up relations with Cuba. 

“There was all this talk about how he’s a lame-duck president but he’s proven in the last few weeks that he still has some juice,” Manley, a former Reid adviser, added. 

One thing Obama may highlight as an accomplishment: the economy. The White House has increasingly pointed to a rebounding economy, planning to use the uptick in economic indicators in the coming months to help define Obama’s legacy. In recent speeches and television interviews, the president has never missed an opportunity to send a clear message that he was the guy who helped oversee the economic bounce. And senior administration officials say it will be a critical part of their messaging in 2015 and beyond.  

5) Why didn’t the president end up going to Ferguson? Can we expect the president to address race more specifically in the future?

The White House contemplated whether it should send Obama to Ferguson, Mo., several times in recent months before ultimately deciding against it — at least for the time being.

In the days following the incident when Michael Brown, an unarmed black teenager, was shot by a white police officer, White House officials decided that a presidential visit would interrupt the work of local law enforcement amid protests. But months later, Obama still has yet to visit, causing some anger in African-American communities. 

And while Obama has committed to helping to ease tensions with local law enforcement, he has stopped short of addressing race relations. 

However, strategists and observers say Obama, as the nation’s first black president, needs to play a bigger role in helping to soothe tensions that have arisen in communities across the country. 

Obama could also face queries on a new task force he established Thursday to examine community policing standards. Aside from endorsing body cameras and new training initiatives, Obama has been vague on how he wants police forces to change. Thursday could be an opportunity to pin down what kind of reforms the president is most interested in seeing.