Machiavelli, Misunderstood Now is not the time to keep our enemies closer than our friends.

By Alexander Benard

After 100 days in office, a discomforting pattern has emerged in Barack Obama’s approach to foreign relations: He is keeping friends close, but enemies closer. Although this might have been a shrewd tactic in the royal court when Niccolo Machiavelli voiced the idea (or when Michael Corleone put it into that memorable phrase), it is not a viable foundation on which the United States can build a 21st-century foreign policy.

To be sure, President Obama has met with the prime ministers of two important American allies, Canada and the United Kingdom, and last week played host to the presidents of Pakistan and Afghanistan; his most visible diplomatic initiatives, however, have been directed at Iran, Cuba, Venezuela, Syria, and North Korea. Obama taped a video message for the Iranian regime and people, offering his best wishes for the Islamic New Year and stating his desire to pursue “constructive ties among the United States, Iran, and the international community.” He smilingly shook hands with Venezuela’s Hugo Chávez and declined to criticize the strongman for removing limits on his term of office. He made overtures to Cuba in what one senior administration official described as a test of whether the two countries could develop a “serious, civil, open relationship.” And during his first month in office, he sent conciliatory messages to Syria and North Korea.

Obama’s supporters argue that this outreach has no downside. If effective, it will enable the administration to solve foreign-policy problems, such as nuclear proliferation in Iran and North Korea, without military confrontation. If it is ineffective, the United States will at least have appeared reasonable and accommodating, making it easier for Obama to garner international support for sanctions or other punitive measures.

But this analysis ignores several important considerations, beginning with the acutely dispiriting effect Obama’s efforts are having on dissidents and human-rights activists in countries such as Iran and Venezuela. Speaking of term limits in Venezuela, Obama said that it is “important for the United States not to tell other countries how to structure their democratic practices and what should be contained in their constitutions.” But the problem in Venezuela, Iran, and Cuba is not the structure of democratic practices, but their total absence. In these and similar countries, advocates of civil liberties and free elections are routinely intimidated and jailed, as are political opponents of the regime. These dissidents need an American president who is willing to cry foul and to encourage their efforts to hold the leaders of their countries accountable.

The dictators Obama has courted so far have reacted to his overtures with contempt rather than courtesy. In Cuba, Fidel Castro suggested that the United States was looking to “return [Cuba] to the fold of slaves.” And Venezuela’s Chávez used his first meeting with Obama to give the president a book titled Open Veins of Latin America, which chronicles, among other things, the alleged abuses Latin Americans suffered at the hands of the United States.

This sort of gamesmanship might not matter much in Latin America. It matters in Iran, where the Grand Ayatollah graciously indicated that he might be interested in talks once the United States renounced its backing of Israel and lifted sanctions against Tehran, and it matters in North Korea, which test-fired a missile in early April. Every passing day allows these countries to further develop their nuclear capabilities.

Our allies, meanwhile, are unsettled. On a recent trip to the Middle East, Defense Secretary Robert Gates was peppered with questions about whether the United States is on the cusp of a “grand bargain” with Iran. Gates replied that the United States will “keep our friends informed about what is going on so that nobody gets surprised,” but the Obama administration can expect allies—including Israel—to be nervous. Their cooperation will be harder to secure if they begin to hedge against what they perceive as an increasingly unreliable partnership with the United States.

That hedging may yet develop into something more sinister. Allies will see a president who glad-hands Hugo Chávez but has no time for Colombia’s President Uribe, one who does nothing to shepherd a free-trade agreement with Colombia through Congress, who sends holiday greetings to Ahmadinejad in Iran but not to Hamid Karzai in Afghanistan or Nouri al-Maliki in Iraq, and who pens a letter to Russia’s President Medvedev offering to forgo missile defense in Poland and the Czech Republic in exchange for U.S.-Russian cooperation in other areas. Our allies may begin to wonder: If all the special treatment is reserved for America’s foes, is there any point in being America’s friend?

— Alexander Benard, a New York attorney, has worked at the Department of Defense and the Washington Institute for Near East Policy.