President Obama’s Trip to Jamaica and Panama: 5 Things to Watch

— -- President Obama will depart Wednesday evening for a three-and-a-half-day trip to Jamaica and Panama for a series of meetings at which the U.S. relationship with Cuba is expected to take center stage.

The president will first travel to Kingston, Jamaica, where he will meet with Caribbean leaders to discuss everything from security efforts in the region to energy, as well as speak to students in Jamaica. It will mark the first presidential trip to Jamaica since 1982.

He then will fly to Panama City for events with CEOs, Central American leaders and others before attending the Seventh Summit of the Americas, which, for the first time, will be attended by all 35 countries in the Western Hemisphere -- including Cuba.

Here are five things to watch on President Obama's trip to Jamaica and Panama.

1. Will Obama and Castro Meet?

All eyes will be on whether an historic meeting occurs between President Obama and Cuban President Raul Castro on the sidelines of the Summit of the Americas in Panama on Friday and Saturday. The White House has hinted an encounter between the two leaders will likely occur, though a formal meeting has not been scheduled. "I'm sure that President Obama will be interacting with President Castro at the summit events and as the leaders gather on the margins of those events," Ben Rhodes, deputy national security adviser, said on a conference call Tuesday. If Obama and Castro do have any substantive talks in Panama, this would be the first meeting between a U.S. president and Cuban president in nearly 60 years -- the latest development in President Obama's efforts to normalize relations between the two countries. Over the past year and a half, Obama and Castro have engaged in limited -- but history-making -- interactions. In December, the two leaders conducted a 45-minute phone conversation ahead of an announcement that the U.S. and Cuba would try to restore diplomatic ties. Obama and Castro also shook hands at a memorial service for Nelson Mandela in 2013. But many are hoping a more substantive conversation could occur on the sidelines of the summit.

2. Cuba Could Be Removed From the State Sponsors of Terrorism List

It could happen at any moment. The State Department started its review of whether Cuba should remain on the state sponsors of terrorism list in December and is nearing the conclusion of its assessment. Once President Obama receives the official State Department review, he will make his recommendation, which could occur during his trip to Jamaica and Panama. Removing Cuba from the state sponsors of terrorism list would be the latest major step in efforts to normalize relations between the U.S. and Cuba. Currently, Cuba, Iran, Sudan and Syria all are on the list. Cuba was added in 1982 based upon accusations it provided weapons and training to rebels in Latin America.

3. Changing Expectations