The First and Last Hurrah

I’m writing this from Intelligentsia in Chicago near Millennium Park, sitting across from my brother, watching snow fly by the window outside. It’s not a terrible way to spend a Saturday morning.

2010 has been a crazy year for my family. One of the seminal moments for us was the engagement of Logan, my brother, to his girlfriend of a few years, Jill. I cannot say for sure, but I think they were engaged in the springtime, and in all fairness, it wasn’t the craziest thing going on in our family at the time.

Back during the summer, I was working on Dad’s political campaign and was going through a particularly stressful set of days toward the end of June, preparing for our financial disclosure deadline, trying to raise as much money as possible to hit our pre-determined goal. In a series of classically-Wes-like angry outbursts, I chastised my brother for something and ended up leaving the office furious with him. I got back to the office, he was gone, and when he returned the following three things happened:

1. He tossed a carton of American Spirits at me. Not a single pack, a carton. The kind you see people walking out of Wal-Mart with on a weekend. This was clearly some sort of peace offering, one he should not have made.

2. He said, “I wanted to ask you to be my best man today.”

3. I said, “Well, I cannot say yes now, not since we had that blowup earlier.”

After that, we agreed to meet for breakfast the next day and talk it out. We did, and since then, I think we would both agree things have been far better in our relationship as brothers. We are rapidly becoming the peers we should have been for the past 8 years as opposed to the older/younger brothers that always fought, sharing friends but rarely at the same time, mutually enjoying getting the other one all worked up over nothing, etc.

Logan and Jill are set to be married in a few weeks in Nashville. In the summer it occurred to me that we had never taken a trip together, just the two of us. In fact, we’d rarely been alone, just as brothers, in years. So, I asked him if he wanted to do a short “brother trip” before the wedding. Sort of a peace offering of my own, but more a chance to get away and spend some time being brothers before he places the millstone around his neck (kidding) and ties the knot. So, this would be a sort of first and last hurrah for our relationship as brothers without spouses.

We picked Chicago for a few reasons. We’d both been to NYC, LA and DC in the past year. We didn’t really want to be rained on constantly in Seattle/Portland. Chicago made sense. We had been to Chicago about 20 years ago, and figured we didn’t remember anything about it other than going to Wrigley Field for a Cubs game in which Ryne Sandberg, my favorite cubs baseball player at the time, sat out because he was already super old or some other lame excuse. This time we’d remember it and do what we wanted to do, nothing else.

So, we board a plane here in a few hours to head home. It’s been fun I think. I’ve had a good time. We’ve seen some amazing art at the Art Institute of Chicago, had great coffee all over, great meals here and here, and walked all over the place. We’ve seen the Navy Pier, Solider Field, the Willis Tower and its “SkyDeck“, Hancock Tower, our hotel rooftop terrace, the Millennium Park open-air concert hall designed by Frank Gehry, that silly bean-thing everyone raves about, the Faces waterfalls in the park, jointly regretted going to the Field Museum (it’s not awesome – anyone who says so is a liar), and so much more. We’ve been tourists, and not the best ones, but we’ve had fun.

So, that’s that. #BrotherTrip2010 is coming to a close. A new chapter starts for Logan. And I’m looking forward to standing by his side as he takes Jill as his bride and they start a life together. He’s already said he wants to come back to Chicago with her. I’ll just make sure she knows to avoid the Field Museum.


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