As 2014 begins, the Foreign Policy experts at Brookings are offering President Obama and his Cabinet a set of innovative and actionable policy recommendations to address the critical foreign policy challenges in the year ahead. As he does every year, the president must decide which priorities to pursue and how best to exercise U.S. power and influence to manage and shape the global order.

“Big Bets & Black Swans: A Presidential Briefing Book” is a series of memos designed to present President Obama as a suggested “to do” list, addressing the most significant foreign policy challenges in the year to come. This year, the memos are divided into five categories: Big Bets, Double Downs, Black Swans, Nightmares and Holds. The Big Bets are issues where Foreign Policy scholars believe the president should consider investing his power, time and prestige in major efforts that can have a transformational impact on America and the world. Double Downs are derived from the Big Bets of 2013. The Black Swans are low-probability, high-impact events that can divert the president and his administration from higher purposes. Nightmares are events that could prove likely and particularly troublesome for U.S. interests and the global order. Finally, Holds are updated recommendations to stay the course on policy approaches put forward in 2013.

President Obama has just three years left in office to define his legacy in world affairs. Now is the time for him to focus on some Big Bets and avoid or mitigate Black Swans to shape the future of U.S. and global security and prosperity.

Click on the cards below to access the individual memos associated with each category. (A summary, video and link to the full memorandum will appear in the white space beneath):

U.S. Leadership of a Liberal Global Order

President Obama’s overarching foreign policy goal in the remainder of his second term should be to reassert American leadership in a rules-based international system, write Robert Kagan and Ted Piccone. The president also needs to lead at home, reminding Americans why continued vigorous engagement in the world is in their best interests.

Secure the Future of the Internet

President Obama should make it a personal priority to ensure an open and free-market Internet in 2014, write Peter W. Singer and Ian Wallace. Instead of waiting out the international blowback from Edward Snowden’s NSA revelations, the president needs to lead a new strategy against those governments who want to regulate the way the global Internet is run.

Solidify the U.S.-Afghanistan Alliance

Former ISAF commander General John Allen and Michael O'Hanlon call for steadiness, patience, and resoluteness in American policy towards Afghanistan in 2014 and beyond, writing that Washington should be willing to wait for a Bilateral Security Agreement with the Afghans until the spring, if necessary.

Lift the Ban on U.S. Oil Exports

Under current U.S. law, crude oil produced in the U.S. cannot be exported without a license. In the meantime, domestic crude oil production and imports from Canada could be well above six million barrels per day through 2040. Tim Boersma and Charles Ebinger urge President Obama to ask Congress to lift the ban on crude oil exports.

Strengthen Stability in Africa

In an effort to build greater stability in Africa, Michael O'Hanlon urges President Obama to deploy U.S. troops to Congo, to bolster the ongoing U.N. mission there. O'Hanlon also argues for the deployment of several hundred Americans to Libya, as part of a larger international mission to establish stability before the country descends into further anarchy.

Broaden the Approach to Iran

Suzanne Maloney urges President Obama to pursue a comprehensive agreement with Iran that not only rolls back its nuclear program, but seeks to induce the Iranian government to adopt more responsible policies toward its citizens and neighbors. The prospective payoff -- a world released from the perennial nightmare of an Iranian nuclear bomb -- justifies the investment.

Pursue Regime Change in Syria

Michael Doran urges President Obama to return to a policy of regime change to end the civil war in Syria. The United States currently appears fickle and risk-averse in comparison with Russia and Iran, which are significantly backing their ally. America’s aloofness harms its global standing, especially in the Middle East, where its will and staying power are questioned.

Return to the Asia Rebalance

While the Asia-Pacific region must be at the core of U.S. national strategy, the challenge is to ensure that this strategy is credible and sustainable, both in the U.S. policy process and in the eyes of those it seeks to influence. Jonathan Pollack and Jeffrey Bader write that President Obama should pursue a combination of political, security and economic policies.

Reach Out to Cuba

Ted Piccone urges President Obama to double down on his 2009 decision to relax sanctions on the flow of people, remittances and exchanges from the United States to Cuba, recommending unilateral steps to expand trade, travel and communications with the Cuban people, and to provide direct support to Cuban entrepreneurs.

Avert Conflict in the South and East China Seas

During 2013, the United States warned Asia's maritime countries of the danger of asserting their claims in the South and East China Seas, and urged adoption of arrangements to reduce risk and avoid conflict. Jonathan Pollack, Richard Bush and Bruce Jones write that the Obama administration should continue along this path in 2014, to help prevent further clashes in the region.

Korean Crisis Prompts China Confrontation

North Korea’s nuclear program poses fundamental security threats for the U.S. and China. Jonathan Pollack and Richard Bush urge President Obama to convey unequivocally to China that the U.S. will uphold security and stability on the peninsula, that U.S. actions are not directed against China and that the U.S. seeks far greater cooperation with Beijing to advance these goals.

Iran Nuclear Talks Fail

While pressing for a sound comprehensive agreement with Iran, the U.S. should prepare for a possible failure of nuclear negotiations. In that event, Robert Einhorn and Kenneth Pollack recommend that President Obama reinforce international support for strengthening sanctions, and for credibly threatening much greater penalties for any Iranian movement toward or across the nuclear threshold.

Afghanistan’s Presidential Election Goes Awry

This year’s Afghan presidential election is taking place as the departure of U.S. and international forces from Afghanistan approaches and as structural weaknesses in Afghanistan persist, imperiling a successful transition. Vanda Felbab-Brown argues that President Obama should adopt a multifaceted effort to support the elections and persuade Afghanistan to permit a continued and stabilizing U.S. military presence after 2014.

Muslim Brotherhood Radicalizes

By declaring the Muslim Brotherhood a terrorist organization, Egypt risks radicalizing the group’s members and destabilizing the region further. Daniel Byman and Tamara Wittes argue that the Obama administration should engage with peaceful Islamists, push Egypt to allow Brotherhood supporters to participate in legitimate political and social activity, cooperate with Egypt on legitimate terrorism threats and expand counter-radicalization efforts there.

Israeli-Palestinian Violence Erupts

Should Palestinian-Israeli peace negotiations fail, Natan Sachs writes that there is a risk of full-blown violence between the parties, coupled by terrorism from Lebanon and the Sinai Peninsula. To prepare, the United States should candidly assess the risk of violence and how to stem it should it erupt, and re-energize U.S. involvement in daily security coordination.

Putin’s Russia Goes Rogue

To punish Moldova, Georgia and Ukraine for their efforts to deepen relations with the European Union, Putin’s Russia could resort to trade sanctions, gas cut-offs and other pressures. While U.S. leverage is limited, President Obama should develop a common line with the European Union that such Russian actions would have consequences for its relations with the West.

Venezuela Breaks Down in Violence

Economic mismanagement in Venezuela is producing widespread scarcity and high inflation, creating the risk of a violent popular reaction and regional instability. Harold Trinkunas recommends that President Obama work with other Latin American countries to convince Venezuela to change its course, and to develop a coordinated response in the event of a violent breakdown.

Avoid a U.S.-Saudi Divorce

U.S. relations with Saudi Arabia deteriorated further last year with major differences over Egypt, Syria and Iran. Bruce Riedel writes that President Obama should try to reverse this slide and regain Saudi trust. The risk of political unrest in Riyadh remains low, but bears watching.

Close the Deal on Free Trade

Much is at stake for the United States in the successful conclusion of the trans-Pacific (TPP) and trans-Atlantic trade negotiations. Mireya Solis recommends that President Obama engage Congress more proactively to secure trade promotion authority, to redouble public awareness efforts on the benefits of trade and to negotiate consistent standards across trade agreements that can be disseminated globally.