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Although President Obama can’t technically be accused of negotiating a deal to keep Iran nuclear weapons free based on a belief that moderates will be running that country by the time the final deal expires, he clearly views this outcome as distinctly possible. But the record of U.S. and western diplomacy versus rogue states and powerful dictatorships generally shows that even such cautious hopes can be misplaced, and that the kind of engagement the president champions can dangerously backfire.

The link between Mr. Obama’s Iran deal and his views about Iran’s political future has been among the major objections of critics like Israeli Prime Minister Binyamin Netanyahu. It’s a huge current issue because Iran is sponsoring lots of terrorism and instability in the Middle East right now and could of course foster more with the nuclear deal sanctions relief – as noted most prominently by former Secretaries of States Henry Kissinger and George Shultz. And it’s a huge long-term issue because of the threat Iran could pose once a successful deal’s curbs expire, if a regime enriched by decades of commerce with the rest of the world decides to seek nuclear weapons once more.

Perhaps mindful of these worries, the president told NPR’s Steve Inskeep that “the deal is not dependent on anticipating those changes. If they don’t change at all, we’re still better off having the deal.”

At the same time, Mr. Obama spoke at length about the chance of Iran reforming during the deal. Two of his points are especially important. First, the president expects that once sanctions are lifted, Iran’s economy would only “slowly and gradually improve.” Moreover, “a lot of that [improvement] would have to be devoted to improving the lives of the people inside of Iran.”

Second, Mr. Obama voiced confidence that “if in fact they’re engaged in international business, and there are foreign investors, and their economy becomes more integrated with the world economy, then in many ways it makes it harder for them to engage in behaviors that are contrary to international norms.”

The forecast about Iran’s likely post-sanctions economic priorities seems like nothing but a guess. He might be right about the minimal additions sanctions relief could initially add to Iran’s capacity for trouble-making.  But as he also noted, Iran has been aggressively trampling all over “international norms” with its economy under pressure. So Iran could indeed lavish most of its new largesse on its people, and still be a major danger.

The second Obama observation could be the most problematic, though. First, it’s not at all clear what, if any, precedents the president has in mind. Major engagement with the world economy has brought many stunning changes inside China. But not only is the regime’s hold on power seemingly as strong as ever. Its international actions recently have become more aggressive as well, especially in surrounding seas. As for Russia, before its burst of expansionism, Vladimir Putin’s government was open to foreign trade and investment. Look what’s happened.  (By the way, as I’ve written, Putin is by no means solely or even largely to blame for mounting tensions with the West. But given President Obama’s stated views about Moscow’s “aggression,” Russia’s recent behavior pokes a huge hole in his analysis of Iran.)   

Worse is a point made in a terrific recent piece by University of Georgia economist Jeffrey Dorfman: If anything, the free world’s relatively modest reactions to recent Russian and Chinese moves strongly indicates that, in addition to trade and investment expansion enabling such countries to have their cakes and eat it, too, they also afford significant protection from retaliation. For the multinational companies doing the most new foreign business with them tend to lobby powerfully against any moves that could endanger current or future profitability. In the case of China, these firms have gone even further on occasion, actively serving as apologists for Beijing’s behavior and policies.

Past is not always prologue, and Mr. Obama may turn to be right about Iran. But these remarks only strengthen the case that his approach to the nuclear deal, and his broader views of engagement with adversaries, stem excessively from the always worrisome practice of assuming the best.