For too long the United States’ only policy toward Cuba consisted of sanctions and non-engagement. Engaging Cuba is the right thing to do. Unfortunately, President Barack Obama is doing it the wrong way.

When Cuba fell to communist control, the United States began covert operations to destabilize the regime and aid anti-communists seeking to overthrow their hardline overlords. For the most part, CIA-backed efforts to wage this covert war were harebrained and unsuccessful. Tim Weiner in his critical history of the CIA details some of the more unorthodox methods contrived by the agency to eliminate top Cuban leaders, including Fidel Castro himself.

Attempts to replace the regime in Cuba ground to a halt with the Cuban Missile Crisis in late 1962. The discovery of Soviet nuclear-armed missiles in Cuba placed an extraordinary pressure in the Kennedy Administration. Desperate to rid the isle of the missiles, which posed a national security threat to the nation and a political threat to the Kennedys, President John F. Kennedy agreed to tacitly recognize the legitimacy of Castro by halting all U.S. efforts to overthrow the regime, and remove outdated U.S. missiles in Turkey in exchange for the removal of the Soviet missiles.

Since that time, the United States has not pressured the Cuban regime beyond the imposition of economic sanctions and travel restrictions. That has been a mistake.

It could be argued that Kennedy’s deal with the devil pledge to not overthrow the Castro regime should have endured for as long as the Soviet Union remained a world power. But when the Soviet Union collapsed in 1991, U.S. policymakers should have seized the opportunity to review Cuban policy and change the nation’s approach to the nearby communist state. No longer were communist powers ascendant or peer threats to the free world, then was the chance start an active – as opposed to passive – policy of destabilizing and challenging the communists that rule from Havana.

There is ample historical precedent for vigorous U.S. policy in the Caribbean and Latin America. The Reagan Administration engaged – covertly – in Nicaragua, and overtly in Grenada, and the Bush (41) Administration engaged in military action in Panama. Much earlier in the 20th Century, President Theodore Roosevelt championed an active interpretation of the Monroe Doctrine in Panama, and President William McKinley in the waning days of the 19th Century waged war against Spain in Cuba (something that didn’t help U.S.-Cuban relations).

President James Monroe outlined his “Monroe Doctrine” in a speech to Congress in December of 1823. Monroe declared that the Americas are off-limits for the colonizing aims of European powers, and that any act of aggression or imperialism by European powers in the hemisphere would be considered a direct threat to the United States. It was a bold policy for a young country.

Unfortunately, in the post-World War II era of the 20th Century, Latin America took a backseat among U.S. foreign policy priorities. The standoff over nuclear weapons in 1962 revealed the dangerous consequences of non-engagement or failed engagement.

With a resurgent Russia strengthening its relationship with Venezuela, and deepening its ties with communists in Cuba, and with China looking to build a competing canal to the Panama Canal (which the U.S. maintains an exclusive right to defend), the great powers of the world today are deeply interested in what happens in the United States’ backyard.

President Obama is right to be interested in changing the United States’ relationship with Cuba. But his timing is off, his negotiation skills lacking, and his intuition about what needs to be done incorrect. According to Bill Gertz of the Washington Free Beacon, Russia concluded a strategic “intelligence and military” agreement with Cuba in May of this year. It would have been preferable to change Cuban policy before this agreement, not after it, when it appears you are trying to play diplomatic catch-up to a competing world power.

What the President managed to achieve so far with his new policy, besides headlines and a prisoner swap, is unclear. The historical nature of his announcement comes more from its existence than any new clear policy that it espouses. Entering the final quarter of his presidency, Obama has so far bungled much of his foreign policy aims both in the Middle East and elsewhere. Making an historic announcement about Cuba assures his place in the diplomatic history of the hemisphere, but little else.

In the spirit of the Monroe Doctrine, Obama should reach out to Latin America and expand and strengthen military and economic ties with key partners, offering a powerful incentive for nations to reject ties with China and Russia in favor of good neighbors closer to home. In Cuba, the president should seek the complete rejection of the communist regime and the liberation of the Cuban people from the heavy hand that has long oppressed them. Doing that will take time and involve effort, but it is certainly better than bowing to a regime stuck in the failed ideology of the last century.