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Fear and Loathing in Chicago

Six lessons learned after a long weekend in the Windy City.

Photo by KAMIL KRZACZYNSKI/AFP via Getty Images

The whole point of a wedding—at least in theory—is to get it all right the first and only time. That goes for everything: the food, the music, the venues, and of course: the bachelor party.

I’ve recently completely that latter leg of my wedding process.

If you were one of the exactly two people (myself being the other) who noticed that there was no Monday Morning Brushback article yesterday, it’s because I spent this past weekend in Chicago celebrating my bachelor party. A group of my very best friends hit the Windy City to commemorate your favorite OTM writer tying the knot this September with Missy Mo Peña.

You may have also noticed that a certain baseball team based in Boston was in Chicago this weekend—once you recall that, you’d understand why we went to the Midwest.

Did it all go right? Well, no—but actually, yes. This post is a bit of a stream of consciousness, so you’ve been warned of any potential ramblings. . . not that I don’t usually ramble on here anyways, but I digress.

Overall, the weekend was spectacular. We hit the Wrigley Rooftops on Friday for that Red Sox victory over the Cubs. Trust me: if you ever get the chance to do the Wrigley Rooftops, take it. That’s the first lesson of this tale. It’s quite the experience. Food and drinks are all included, there are no lines for the bathroom, and if you pick the right rooftop it gives you an awesome view of the Friendly Confines.

Yet this post isn’t about Friday night at the ballpark, or any other part of exploring the city. Oh, if only it were that simple.

No, it’s a tale of pits and peaks; making the most of shitty situations, if you will.

My dad, my two uncles, and myself were all set to head back to Boston Sunday afternoon. We got through security at O’Hare International Airport with quite enough time to spare and with no issues—routine stuff before a flight. By chance, we bumped into two of my buddies who were hopping on our flight (key word is our flight; more on that later) and we all decided to grab a few drinks to pass the time.

In my experience, airplane delays are not one-off things, as one hiccup usually leads to another. Our 3 p.m. flight first became a 3:30 p.m. flight, as Boston was experiencing some nasty weather. I already half expected another kickback, so I wasn’t shocked when we got another change to 4 p.m. Whatever—more NBA Summer League and golf for me to watch at the bar, I suppose.

You know the old saying “bad things come in threes,” right? That’s the second lesson of this tale. That saying is 100% true.

I took a sip of another over-priced brew right as one of my friends starts cackling laughing upon seeing another notification from American Airlines. Our plane, unfortunately, tweeted something racist a decade ago and had been cancelled as a result. No additional delay, no rerouting, nothin’. Just no more flight.

My friend’s reaction to this news is your third lesson today: sometimes, a situation gets to be so fucking stupid that all you can do is laugh. Realizing what is and is not in your control and reacting in line with those realities is an important trait to possess.

We soon came to the collective realization that the only things left to do were to stay on the ball for any updates from American, keep sluggin’ those brews, and to name random baseball players. Shout out to the group that I was with, because there truly is no more quintessential “Dudes Rock” experience than naming random ballplayers from years past. Todd Van Poppel! Lyle Overbay! Darren Oliver! Ted Lilly! Shea Hillenbrand! The Molinas not named Yadier! It was like playing an endless game of Immaculate Grid.

That’s lesson number four: any situation—no matter how frustrating, confusing, annoying, boring, any “—ing” combination you can think of—can be improved by the company of those with a shared, lived experience. Humans are social creatures by nature. We were able to befriend complete strangers from different countries and different destinations within our terminal solely through the connection of sport. Hell, a kid from Sweden made fun of me for being an Arsenal fan after that just so happened to come up! Wrong sport, sure, but my point remains!

And hell, isn’t that what sorta brings us to this very website in the first place? Just about none of you know me in my personal life. . . unless you do, then you’re either making me very uncomfortable or you’re my mom (hi Mom). Point is: you, dear reader, appreciate one of my favorite things in the entire world. You’re a baseball fan; how bad can ya really be? We’d get along if we were at that bar together on Sunday, I’m sure of it.

Anyways, we eventually come to find out that my dad, one of my uncles, and I were unable to be added to a standby list for other flights going to Boston. Remember how I mentioned “our” flight back to Logan earlier? Yeah, other flights went off without a hitch. . . flights that featured my second uncle along with those two friends we reunited with. They were the lucky ones, as we came to learn that the earliest we could get a flight back was Tuesday afternoon — the time I’m writing this. Don’t ask me why we got the short end of the stick because I don’t know.

We were left with no other choice but to rent a car and drive from Chicago to Boston after staying the night at one of the hotels near the airport.

That brings me to the fifth lesson here: if you are over six feet tall like myself, do not—under any circumstances—get in a standard-sized car and drive halfway across the country in one day. Do yourself a favor and break up the trip with an overnight bit to rest, at the very least. Walk if you have to. At least you’ll be able to stretch your limbs out.

Fourteen hours in a rented car that would probably cost as much as a seat for a later flight was quite the decision, and one that’s left me with quite the sore left shoulder even now. But, we made the most of it. More baseball talk for hours and hours between us three, with the help of the WEEI broadcast from Oakland Monday night, helped matters. It was another testament to lessons three and four that I’ve outlined here.

That’s a good transition to my sixth and final lesson, the one that I think is probably the most important and all-encompassing one:

So much of life is about perspective.

The late Hall of Famer Roy Halladay had a tweet a few years back that I thought about a few times during this entire episode.

I’ve quoted Hannah Montana a few times already during my OTM tenure, so what’s one more being added to the bunch: life’s what you make it, so let’s make it rock.

Years from now—when I’m recounting these travels with Missy Mo Peña alongside our kids and their grandpa—how am I gonna portray it? Was it an awful ordeal full of headaches and a lack of sleep, or was it one more group of special memories following a weekend packed to the gills with them? Was it a long countdown to the sobering reality of heading back to everyday life, or was it an ongoing celebration of what brings us together (baseball most certainly included)? Was I jealous that almost everyone else in our group was able to fly home without any trouble, or was I thankful that all of those friends were able to take time out of their lives to come halfway across the country in the first place?

I know what my takeaways will be.

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