On May 11, 2006, I had the following conversation in IRC (I'm target):
16:32 < mjlewis> ok, what's the line on the president's approval rating going under 25%?
16:32 < mjlewis> or under 50% with republicans?
16:32 < target_> 25% no way.
16:33 < target_> I put 25% at 400:1 against.
...
16:39 < hubt> what's the time limit on 400:1
16:40 < target_> while he's still in office.
16:40 < paladinMO> the gambooler awakens
16:40 < paladinMO> can i bet $1?
16:40 < target_> sure
16:40 < paladinMO> $10?
16:40 < target_> sure
16:41 < paladinMO> hm. maybe i should bet $25, and if i win, i enter the wsop.
16:41 * target_ is getting a little nervous about the amount of money he may be putting on the table
16:41 < paladinMO> so do you really want to lay me 400:1 on his popularity dropping below 25%?
16:41 < paladinMO> on a $10 bet?
16:42 < target_> I think I'm going to back out just because I'm unexcited about the downside variance
16:42 < target_> but I'll do it for $1
16:42 < paladinMO> i figured.
16:42 < paladinMO> ok. done.
And I, even though I was just arguing about a line and not offering it, accepted. My ego got in the way.
Now, even if I thought that the line was right -- and it wasn't necessarily well-thought-out, so I really didn't have much confidence in it -- I shouldn't have taken it. If I'm wrong in my favor, I make a few pennies. If I'm wrong in his favor, I can be out tens of dollars of EV or more. Not to mention, he'd take a worse bet than that, so I had no need to lay those odds.
On the upside, it really was very unlikely. There is a core of die-hard supporters who will hear no wrong of the man (just as there will be for Obama). In american politics, it is unbelievably hard to have an approval rating below 25% -- Nixon managed it, with 23%, but he's the only one. The war would have to go badly, and on top of that we'd need to have some sort of domestic catastrophe, like a bad recession or a market crash, or both... and then we did.
Here's what Bush's approval/disapproval graph looks like in the last few years:

My bet was really not looking so good there.
Jason graciously let me choose the poll, and I chose the Fox News poll. Actually, that was another mistake. While Fox News as an organization is undeniably right-leaning, their polling data is not. It's middle-of-the-road, and in the recent election, had no serious house effect. However, they were noisy, which is really awful, since a couple points in the wrong direction and I'd be done for. I should have chosen NBC-WSJ, who were pretty consistent and had a 2-3 point republican lean, and who would not have been quite so transparent a choice. On the other hand, I hadn't read
538.com's analysis of house lean by then, since Nate hadn't written it, so I'm not sure how I could have known. For the record, NBC-WSJ never had Bush go below 29. CBS, in contrast, had him as low as 22.
Fox News just released
their final poll on Bush's popularity:
1. Do you approve or disapprove of the job George W. Bush is doing as
president?
*** Bush Job Ratings Summary ***
Approve Disapprove (Don’t know)
Most recent (13-14 Jan 09) 34% 58 8
Highest (14-15 Nov 01) 88% 7 5
Lowest (8-9 Oct 08) 25% 69 5
Job Rating Averages:
First Term 61% 29
Second Term 37% 55
Entire Presidency 51% 40
So the lowest he went was 25%... and not below, so I win the bet. Phew.
I should frame that dollar, or something.