Dear Barry

06.04.08 | Filed Under Americana

I’m so glad you know better than to listen to the likes of me …

TITLE: So Barack Obama Walks into a Bar …
DATE: January 17, 2007

Hey. How are things? You look good. Of course, you always do.

Yeah, I did hear about your Exploratory Committee. That’s great. I’m really happy for you. Glad to hear you’re doing well for yourself.

But that’s actually why I wanted to meet up here. Why don’t we sit down for a sec? What’s your poison? I’d ask you to get comfortable, you know … unbutton your tie and all … but I can see you’ve done that already.

Look. You know how much I like you. Riding on the Metra into Chicago those bitterly cold mornings in early ’04, I used to stare at the giant Obama sign on my route, beaming. It was exciting to see the beginning of a poltical juggernaut. It was exciting to see a political sign facing the south side of Chicago. You were hopeful, idealistic yet practical, careful and charismatic, charming, good-looking and perhaps the most eloquent American speaker we’ve seen since that Reagan fella. [ed. note: Yeah, I just compared Obama to Reagan … deal with it.]

But … I have to tell you … and I only say this because I care about you … but this whole ’08 thing scares me a bit.

Please understand … I want you to be president. To be honest, I can’t think of anyone I’ve ever wanted to be president more than I want it for you. I can’t think of anyone that would be a better leader for us. Now or in the future. That may sound like fawning, but it’s really not saying much.

I just … I just don’t want to see you get hurt.

America is a fickle mistress. And you just made eyes at her from across the bar. And America’s gonna respond, especially if she knows what’s good for her. But looking at her, I’m guessing she’s a local … she comes here often. She’s gonna be sitting on that stool next Friday, and probably the Friday after that. Just a guess. You don’t have to make your move tonight, dude.

I don’t want to see you lose an election. I know you’ve lost in the past, but it wasn’t on a national stage. You have yet to fail right now, but let’s be honest … you’ve also yet to really prove yourself. And people are going to hold that against you after a while. And if you lose (which in ’08, I think you would, sadly) … people will definitely think less of you. I think it’s important that you become president someday. And I’d hate to see you diminish your chances just because the media has issues with premature adulation.

America just really likes you right now … so why not keep flirting for a while? You’re having fun, right? Don’t push things too far, too fast. Come back when you’ve been a senator for a while … and in the meantime, spearhead some good work. Show us what you can do. Make it impossible for us to say no to you.

Just some friendly advice. You know what you’re doing. You’re going in with your eyes open.

And lord knows, I’d never follow this advice.

Anyway, it’s been great chatting with you. And seriously, those threads are nice. Don’t worry about the check, I got it. You got me next time.

Man. How fearful of me. I should have more faith in people.

I’m looking forward to the next few months. I’m looking forward to John McCain being the worst-case scenario … as opposed to living in an even worse-case scenario.

I’m looking forward to seeing America choose Obama. I want to watch that happen. I want to see how that works. I’m going to watch carefully, so I can tell my kids exactly how a revolution happens.

Because I do think Obama is the The Real Deal. I think he means it, and that he has the capacity to lead a nation to do Great Things. I’m not worried about him sleeping with Gina Gershon. I’m not worried about having to apologize for him.

I really hope that he gets the chance to show us that we don’t have to accept the mediocrity (and worse) that we’ve been saddled with for the past 45 years. I mean, anyone younger than that can’t even conceive of having an unscandalized president. I look forward to genuinely considering the possibility that I could get behind a viable national political figure.

So, Barry … just don’t let me down.