Would George W. Bush have negotiated and signed the JCPOA with Iran? Even for those who (like me) worked in the Bush White House, that seems like a silly question. After all, who cares? Bush has been out of office for more than six years, and refrains from commenting on foreign affairs or from criticizing President Obama.

But actually it is a very interesting question because it produces some interesting answers— for two reasons.

First, to answer the question is to learn something about Obama and negotiations. Most Republicans think this is a bad deal. Many Democrats agree (even if they plan to vote for it), especially Iran and nonproliferation experts who are Democrats. No one really likes the agreement. The French have been complaining for months about the U.S. handling of the negotiations. It is a bit odd that the P5+1—including Russia, China, the United States, and the EU—could not outmaneuver Iran, a country of only 70 million with a weak economy. Moreover, Iran has an oil economy and oil has come down in price by 50% in the last year. Sanctions were biting. And Iran’s support of Assad in Syria, of Hezbollah, and its own military forces in Iraq and Syria was expensive.

So what happened? Simple, I think. The Iranian negotiators knew full well that their boss had grave doubts about entering any agreement with the Americans, so the conditions had to be terrific for Iran. The U.S. negotiators knew their boss was desperate for a deal with Iran and at bottom would sign anything he thought he could get away with. In important negotiations like this one, the president –in any administration-- makes all the key decisions. Example: Reagan walking away from Gorbachev at Reykjavik despite the advice of most of his key staff. The American negotiators with Iran knew that the “no deal is better than a bad deal” rhetoric was just spin, and they knew how badly Obama wanted an agreement. This was his legacy. They had to produce. They could threaten to walk away but they could not walk away. Obviously, the Iranians knew all this and made it work for them.

Obama and his minions are now arguing that this compromise agreement was the best available: nothing more could have been gotten out of Iran. Nothing. Everything in it had to be there, and nothing outside it could have been added. Nothing. Kerry and Obama get angry when people ask why we could not insist the hostages be freed, or why the arms embargo ends in only five years. They must bluster and insult questioners because the real answer cannot be uttered: we could not challenge Iran’s red lines because maybe then we would not have had a deal. And for Obama, no deal was not better than a bad deal. No deal was a calamity that had to be avoided at all costs.

Second, to answer the “Bush question” is to learn something about how Obama sees the world. Actually, we re-learn  it if we were paying attention to his Cuba reversal. In that negotiation the United States got nothing. Castro got plenty. So why did Obama’s staff negotiate and sign such a deal? Same as Iran: they knew their job was to produce a signed deal, not to insist on strong terms and a balanced compromise or to walk away. And like the Iranian regime, the Castro regime knew this. Thus the outcome.

In Obama’s world, the United States must apologize for past wrongs like the boycott of Cuba or the overthrow of the Mossadegh regime. You might ask, Why was there a boycott of Cuba in the first place, or a Cuban Missile Crisis? What about the Iran hostage crisis of 1979? And don’t historians say the British, not the CIA, overthrew Mossadegh? These are not questions Obama is asking, because he has fixed views—has had, apparently since college. Ask Rashid Khalidi or Jeremiah Wright or Bill Ayers. America was wrong, a bully, militaristic, on the wrong side of history, and now he will correct all of that. That’s his legacy. He can’t do it all but he’ll do as much as he can.

So our negotiators know what he’s after, and they know the details of these agreements don’t matter to him in the grand swing of things. This is History, capital H.

And in the course of History, per Obama, Cuba means Castro, and Iran means the Islamic Republic. Egypt once meant Mubarak, and now means Sisi. It’s a giant pain when the Castro regime jails an American, Alan Gross, because that slows down ending the boycott of Cuba and embracing the regime. Same with the Green Revolution in Iran in June 2009: that slowed down abandoning American policy and reaching the JCPOA we have today.

For Obama and this effort to make History, the Egyptian or Iranian or Cuban people are an obstacle, not the object of the endeavor. That’s the key difference with how Bush saw foreign policy. The Freedom Agenda was ultimately about people, not countries or rulers, and the goal was to empower them. In his Cuba deal Obama has further empowered the Castros, and in the Iran deal he has further empowered the Ayatollah Khamenei. After all, it isn’t really “Iran” getting to spend the $150 Billion, nor is it the Iranian people; it’s a cash transfer to Khamenei, wholly in his control. The perversity of this is clear when we realize that in the medium run, the only solution to the problem of Iran is the people of Iran. They appear to loathe the Islamic Republic, and once it is gone Iranian foreign policy will not consist of an effort to support terror and destroy Israel and oppose the United States. This nuclear deal ignores the people of Iran and strengthens their oppressors, just as in Cuba.

This Iran agreement is a good one only if you have a fixed view of world politics that is built around a deep desire to make up for past American sins by apologizing to the regimes in power and signing agreements with them no matter what. Obama has made History here, no doubt, just as with his Cuba deal, but the pattern is clearer and clearer: his way of making History always seems to reward America’s worst enemies and ignore the populations they rule. The deals he strikes are unbalanced because ultimately he does not care about balance, or better put he believes he is striking a historical balance by righting past wrongs. And he isn’t going to let mere populations get in the way.