President Obama will visit Cuba – the first visit from a sitting United States president since Calvin Coolidge in 1928 – next week.

As Cuba continues to be in the headlines for many reasons, we need to examine the one thing that will change how we deal with Communist countries for centuries to come. The trip to Havana by President Obama is the latest surprise in the high-speed thaw in U.S.-Cuba relations. The visit in March will be historic and captivating. But before the celebrations begin, some tough questions must be answered about the timing and the payoff.

The Cuba policy whirlwind began with the announcement fifteen months ago that secret back channel negotiations had yielded a deal on a prisoner swap and a step-by-step path to normalization. Some travel and exchange restrictions were lifted and, last summer, diplomatic relations were restored. In August, the U.S. embassy in Havana reopened for the first time in 54 years. Last month, agreement was reached on resuming commercial air travel. And now the latest step is the President and the First Lady visiting Havana to meet with Fidel and Raul Castro.

For President Obama, the trip will be spun as a capstone to his foreign policy legacy of engaging past enemies. After the half century of isolation that failed to extract the Castros or the Communist Party from power, Obama is embracing our former foe. The rapid pace of détente, and even the visit itself at this time, is a gamble that cuts both ways.

Timing of the visit was no doubt partly a result of the president’s limited time left in office. The hasty trip was probably an attempt to go to Cuba before the U.S. campaign season gets into full swing. The White House likely envisions that a successful visit will also increase pressure on Congress to lift the trade embargo, first imposed in 1960 in response to the nationalization of American companies without compensation.

While a splashy Cuba trip may make sense for this president at this time, the benefits of the trip should be based on the answer to these five questions.

1. What is the Cuban government getting out of it? The optics of the trip will be priceless advertising for the Havana regime. Photo ops will likely include the American President shaking hands in friendship with the Castros, attending beautiful gardens and beaches, touring historic sites. This sanitized version of modern Cuba will no doubt be accompanied by soaring rhetoric about extraordinary moments and the victory of diplomacy over obstinacy.

2. What are the Cuban people getting out of it? Cuba has barely begun to open its political space. The nonpartisan Freedom House ranks Cuba as the only “not free” country in the entire Western Hemisphere. Basic rights of expression and association are stifled. Freedom House also ranks Cuba among an elite club of “the worst of the worst” on press freedom. We know that local independent Cuban media won’t be covering the President’s trip because there hardly is any. The White House promises to raise uncomfortable questions about human rights with the regime. But will they be taken seriously or fall on deaf ears? Will the president meet with dissidents and get the real story?

3. What are the ramifications to the economy? The island is still a one party Communist state. The government heavily dominates the economy and allows only highly-limited private enterprise. On the Heritage Foundation’s 2016 Index of Economic Freedom, Cuba ranks 177th out of 178 nations, beating only North Korea. Will the visit accelerate reforms or enable continued suppression of economic opportunity?

4. What are Cuban-Americans getting out of it? Polls show that the majority of Cuban-Americans support normalization. Many no doubt hope that closer relations will lead to greater exchange, more openness, and, eventually, restitution for expropriated assets. Will the trip help Cuban-Americans get their homes and businesses back?

5. Most importantly, what will the American people get? Better beach vacations and cigars are fine, but U.S. foreign policy is about advancing American security and promoting freedom. Will President Obama’s trip be successfully leveraged to hasten reforms in Cuba or not? Will the trip be remembered as a bold move to accelerate the march of freedom? Or a mistake of premature reconciliation that was too soon to be turned into real gains?

Ultimately, the wisdom of the trip at this time will be judged on whether it increases or reduces U.S. influence. If Cuba is truly on a path to democracy and free enterprise that continues to progress—leading to a lifting of the economic embargo and eventually free elections—it will be a pivotal moment for a legacy for President Obama. If Cuba is no freer and reforms stall, however, the visit will be viewed as the final naïve appeasement of an unrepentant regime by an impatient outgoing administration. It’s a high-risk bet.

Todd Moss, a former Deputy Assistant Secretary of State, is chief operating officer of the Center for Global Development. He’s also the author of the Ryker diplo-thriller series, including "Ghosts of Havana" out later this year.