Sebastian pointed me to this article by Brian Doherty who quotes Alan Gottlieb:

The invalidation of handgun bans throughout the country, accomplished in the space of two years, was sudden and surprising even to those who have spent decades laying the groundwork. Take Alan Gottlieb, founder and president of the Second Amendment Foundation, which began backing Gura’s various gun lawsuits after Heller. Since founding the SAF in 1974, Gottlieb has been hosting academic conferences, supporting legal scholars and historians, and filing carefully targeted lawsuits in defense of gun rights. Still, he says, “six years ago if you had said [the gun rights community would] see two cases get to the Supreme Court and two victories, I would have said, ‘Not in my lifetime. Maybe in someone else’s.’ ”

Gottlieb attributes the rapid turnaround in part to the brazen overconfidence of gun controllers. If Washington, D.C., had not challenged the March 2007 appeals court decision overturning its highly restrictive gun ban, the Supreme Court would not have had the opportunity to declare in Heller that the Second Amendment guarantees an individual right to arms. If Chicago had not insisted on maintaining its gun ban after the Heller decision, there would have been no McDonald, and the question of whether the Second Amendment binds states and cities would have remained unsettled. “We needed a little luck, and the other side gave us that luck,” says Gottlieb. “Our opponents are our biggest supporters.”

I had a long talk with Alan last November where he said essentially the same thing. My notes on that part of the conversation are:

We win because the other side screws up. All the big wins such as the 1997 I-676 in Washington state, Heller in D.C, and McDonald in Chicago could have been avoided if the other side “had been smart”. As soon as D.C. lost at the appeals court level they could have made a minor tweak in the law and we would have had to start over at ground zero and it would have decades, if ever because the court would have been stacked differently, before we could get it to the SC. Same thing in Chicago. I asked, “Do you really think they are stupid? If not then why are they screwing up?” “No. They aren’t really stupid”, he said. They have “true believers” who see things in black and white. He didn’t say it but I immediately thought of GOA on our side. “Politics is the art of the possible. Not the perfect”, he said. They haven’t been playing the game that way and they have been losing because of it. I didn’t ask but have been thinking that perhaps there is some way we can encourage them to keep screwing up.

Think about that.

They screw up and we win.

There are two lessons there. One is we need to encourage them to keep screwing up. And the other lesson is that we can screw up and lose. We can have too much overconfidence. We can be too aggressive. We can go for it all and they can win.