Then, I realized what it was I was feeling about Jeb: I just felt bad for him.
Feel bad for a two-term governor of a state and the scion of the first family of Republican politics, you say? That's either a) stupid or b) condescending (who the hell am I to feel bad for Jeb, after all?)
Be that as it may, it's how I felt. And, it's how I've felt about Bush for much of this campaign.
He entered the race way back last spring as the clear front-runner — a status confirmed upon him by his last name, his expected financial juggernaut and the depth of his résumé.
But, early on, it became clear that Bush wasn't just rusty at this campaign thing, he simply wasn't all that good at it. It also became clear that Bush was badly miscast for an election cycle in which the Republican base wanted anger from its candidates. The rise of Donald Trump — and his relentless attacks on Bush as a "low-energy person" — only served to highlight the disconnect between Bush and his party's base.
Last night, as he has throughout the campaign, Bush painted a picture of a complex world — from the Middle East to here at home. His answers to questions were larded with detail and complexity. On Trump's call to ban Muslims from entering the country, for example, he was measured and thoughtful; "every time we send signals like this, we send a signal of weakness, not strength," Bush said.
For almost every one of those answers, the crowd, which was not pro-Trump by any means, greeted Bush's response with polite applause. You could almost imagine them leaning over to their friend in the crowd and saying: "Jeb's so nice. And so smart." Of course, they also almost certainly won't vote for him.
I think, at some level, Bush understands the ridiculousness of his current situation. You could see it written all over his face last night — especially when he and Trump were going back and forth over the Muslim ban.
The simple truth is that Bush is either unwilling or unable to play the game that Trump has mastered in this race.
Jeb seems like a nice man who has learned nothing during the long course of this campaign— Joshua Green (@JoshuaGreen) January 15, 2016
Jeb knows the world is complex. He knows that problems aren't solved simply because you say so. He knows the work of governance is hard.
And yet and yet and yet. Bush, as Trump likes to remind him, is at 3 percent while Trump is at 33 percent.
So, yes, I feel badly for him. He's hopelessly miscast in this race and, worst of all, he knows it.