He says it was going into the libyan civil war without a plan, which is a good contender, but I think it was spending a year and a lot of political capital claiming to be working on fixing healthcare as he made it worse when he should have been working on economic reform. My second choice would be failing to do economic reform at any point. My third would be creating global leadership vacuum as he tried to lead from behind. My fourth would be either the Syrian mess, the Libyan mess, or the deliberate provocation of Putin with the Ukrainian mess.
What say you?
I'd say that was a fairly big one; did he remember to note the part where we didn't simply "go in without a plan", we actually
armed militia groups and then lost track of the cash and gear?
I think his biggest failing is a combined failing on the healthcare/economy front, as to his approach. Namely,
1. He should have burned all political capital necessary to obtain the size of stimulus economists recommended, and should have tailored it to bypass/override the APA and various existing procurement/etc policies used by agencies. The latter point would be necessary for having truly shovel-ready jobs. Specifically, we're going to have to pay trillions over the next 10-30 years to deal with an infrastructure that's falling apart. We should have put a ton into meaningful dam, bridge, highway, waterworks, sewer, etc repairs. And he should have had a plan ready the moment he stepped into office.
2. He should have then moved on to health care reform. But instead of saying "hey, congress, why don't you get something on my desk in 6 months? You know, like that **** I was saying on the campaign trail," he should have walked in with his very own
detailed plan, structured exactly as the one on which he campaigned.
I'd add another failing: thinking that acting aloof and above-it-all would somehow cause the "change" he wanted voters to hope for to come into being. It didn't. He managed to alienate his own party in large part. That, plus a pointlessly hostile GOP, made it impossible to do much legislation after his initial burst.