Not for his economic policies, which still remain in force to this day, or for his Central America policy, which did more harm than good, and certainly not for Grenada, but for his Iran strategy.
What? Hear me out. In attempting to deal with a troublesome theocratic regime in control of Iran, Ronald Reagan sought to pursue quiet diplomacy with the mullahs and clerics who sustained the Supreme Leader, Ayatollah Ruhollah Khomeini. Iranian proxies were holding hostages in Lebanon, and Reagan was desperate to get them out without having to pull something as foolhardy as Desert One (and the 1983 Beirut bombing of a Marine Corps barracks probably scared the Shinola out of him when it came to using force in the Middle East). So he approved a secret strategy to trade low-grade, low-priority military hardware for the release of American hostages in Lebanon, ultimately getting three of them released before the operation was exposed in November 1986. Attitudes toward Iran were still bitter with the hostage crisis of 1979-81 still fresh in people's minds in 1986 (including, I suspect, the mind of a 40-year-old real estate developer named Donald Trump), though, and the operation did not go over very well with the American people. After having vowed never to deal with terrorists, Reagan seemed to be doing just that. How could he do such a thing?
To understand why he did so, you have to look back at what was happening in the 1980s. Iran was slowly gaining influence in the Middle East and was in a protracted war with Iraq, then under control of Saddam Hussein. In the interest of playing Iran as a counterweight to Iraq, reducing Soviet influence in the region, and trying to quell the civil war in Lebanon, Reagan sought to deal with the Iranians in secret to improve relations with the Khomeini government. Robert McFarlane, President Reagan's third national security adviser, summed up the reasoning for a rapprochement with Iran in the following memo from June 1985: "Dynamic political evolution is taking place inside Iran. Instability caused by the pressures of the Iraq-Iran War, economic deterioration and regime in-fighting create the potential for major changes inside Iran. The Soviet Union is better positioned than the U.S. to exploit and benefit from any power struggle that results in changes from the Iranian regime . . .. The U.S. should encourage Western allies and friends to help Iran meet its import requirements so as to reduce the attractiveness of Soviet assistance . . .. This includes provision of selected military equipment."
So, Reagan was trying to make nice with the Iranians rather than make war on them. And he did so over the objections of Defense Secretary Caspar Weinberger and Secretary of State George Shultz. There was just one problem, something Weinberger and Shultz sensed - the Iranians were never really interested in any sort of rapprochement. Reagan was sincerely trying for a major foreign policy breakthrough not unlike Nixon going to China, but Khomeini, unlike Mao, was never going to meet with the enemy. He played Reagan for a fool. That's not Reagan's fault. Khomeini could have reciprocated for the good of stability in the Middle East, but he preferred to humiliate the U.S. instead. But, given Trump's current saber rattling, Reagan's explanation of his Iran operation in a televised address to the nation on November 13, 1986, sounds quite reasonable: "My purpose was . . . to send a signal that the United States was prepared to replace the animosity between [the U.S. and Iran] with a new relationship . . .. At the same time we undertook this initiative, we made clear that Iran must oppose all forms of international terrorism as a condition of progress in our relationship. The most significant step which Iran could take, we indicated, would be to use its influence in Lebanon to secure the release of all hostages held there." I thought at the time that we were headed for a war. Silly me. If Reagan had tried to do what Trump is doing now, I would have been more justified in that fear.
But what about the scandal? The scandal involved the proceeds of the money received from the arms sales going to help the Nicaraguan rebels - the contras - which was illegal. We remember the Iran-contra affair as a scandal, but it was the contra part, not the Iran part, that was the scandal. And that was orchestrated by John Poindexter and Oliver North without Reagan's knowledge.
Reagan survived the scandal, and looking back on his efforts to set things right with the Iranians, it must have seemed like a good idea at the time - certainly better than starting World War III. His strategy had this much in common with Desert One, though - it would have been a positive game-changer had it worked. :-(
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