You’ve Never Seen Wrigley Like This Before
The ultimate Wrigleyville tour, as told by a “garbage kid"
Back in the ‘60s, Jess Middleton was a garbage kid.
As in: he spent his afternoons in the stands of Wrigley Field picking up trash in exchange for free tickets to games. He’s the kind of “back in my day” Cubs fan who talks about America’s favorite pastime like it’s still America’s favorite pastime.
Which also makes him the ideal Wrigleyville tour guide.
A Wrigleyville Detour guide, to be exact — Detour being a new urban exploring app from former Groupon CEO Andrew Mason that finally launched in Chicago last week.
You’re probably thinking: “Why do I need a sightseeing app? I’m a local.” But Detour’s different, offering guided GPS tours narrated by local experts who know the city better than you ever will. The result is a seamless, go-at-your-own pace walking tour with high production values and powerful storytelling twists. You can view the available tours here. Each tour lasts about an hour. And do note: there is actual walking involved, but you need more of that in your life, anyway.
As for Jess Middleton’s baseball-focused Wrigleyville tour, allow us to be the first to say: we went, and we can’t recommend it highly enough. It’s a must-do not only for baseball fans, but for any Chicagoan looking for a shot of nostalgia.
We sat down with the former garbage kid to discuss the new sightseeing experience, why the “Friendly Confines” are so friendly and what exactly would it mean if the Cubs actually went all the way this year.
Because if there were ever a year to brush up on your Cubs history, this is it.
Photo: Jonathan Daniel/Getty Images
InsideHook: Tell us more about your experience as a “garbage kid.” That an official title?
Jess Middleton: It’s a name my dad would call me. But there was engineer’s room under the stands, and the engineers would call us ‘garbage kids,’ too. Imagine 30-50 kids rushing over to Wrigley just to get a chance to hold a potato sack. They’d give each kid a sack and a section and we’d pick up trash. In return, you’d get a four-inch piece of paper that just said “one free admission to Wrigley Field.”
That’s it? Nothing else?
JM: Nothing else. No date, no nothin’. Back in those days I guess they didn’t care. You’d take that home and protect that white piece of paper with your life.
I bet. Now, take us back to Wrigley Field back in the ‘60s. On the tour, there are lot of your personal stories about Wrigley being a neighborhood ballpark. How important is that, really?
JM: Well, you have to grow up in the neighborhood to really know. I grew up five blocks away from the field, and back then, Wrigley’s overall impact was felt by everyone. Baseball was all anyone ever talked about. Everywhere we were, you’d hear the Cubs. There was this overall sense of history and pride in the place, and it was right there in our neighborhood. I’d walk 10 minutes and watch players park and beg ‘em for autographs. You’d go to games and see everyone you know. Opening day was like second Christmas. It was our own little town away from Chicago.
Do you remember your first time at Wrigley? Tell us about it.
JM: It’s not the first, but I could tell you about my absolute favorite memory. We were sitting up right behind the Cubs dugout. There was a play. I forget what play. But Leo “the Lip” Durocher came running out of the dugout, and he was swearing, man. He was throwing all kinds of f*cks and sh*ts to the ump. I never heard anyone swear like that in my life. And I was a kid, of course, very impressionable — I’ll always remember that because my dad turned around, looked at me and told me to never repeat anything I heard.
Another favorite memory: my brother and I were there when Billy Williams received the Silver Slugger Award. They presented it to ‘em right by the Cubs dugout, and we were right there. I was literally 15 feet away from him.
Photo: Jonathan Daniel/Getty Images
Going to Wrigley Field now is obviously a completely different experience. For starters, the neighborhood. From your perspective, how has it changed?
JM: When I was kid, Wrigleyville wasn’t Wrigleyville yet. It was just Lakeview, and Wrigley Field meant baseball. Plain and simple. And it was a real Chicago neighborhood. By that I mean, it was all Chicagoans. And back then, the neighborhood was full of kids. I mean, full of kids — that’s what the neighborhood was all about. And we were all poor, came from working-class families. We had the Salvation Army. We had the YMCA. And we had Wrigley. There were no other thrills. Right around the ‘80s is when it really started to change. All these bars started to open up. Young professionals started moving in. Now, neighbors don’t really know each other. They’re from 50 different states. I don’t think you can walk down the street anymore in Wrigleyville and have a conversation about the Cubs, because this guy is a Hawkeyes fan, and this guy is a Tigers fan.
What about a Sox fan?
JM: Ha! Back in my day, don’t come walking around Wrigley. We’d give you sh*t. All playful stuff, anyway.
Another favorite part of the Detour was your discussion on the business of baseball and business — specifically, all the renovations by the Ricketts family, including the Jumbotron that went up last season. How exactly does a fan like yourself reconcile between, say, the commercialism of the game, and your own love of the game?
JM: Baseball has always been the owners versus the players. Players just wanna play day baseball; the owners just wanna make more money. Today, commercialism is absolutely necessary. You can’t have a team unless you have all these revenue sources. I’m a baseball purist. I didn’t like the lights [Ed. note: Wrigley was the last stadium to get night lights, in 1988]. I wish baseball was still in the day, in the sunshine. And I wish it was still all about baseball. Back in the day, players weren’t looking at themselves on big Jumbotrons. They were just playing the game. But it’s all necessary. It’s just something you have to deal with.
If they win it all this year — can we say all the changes have been worth it?
JM: Look at it this way: we’re never going to win the World Series if the team can’t afford the players. Anything that has to happen for the Cubs to win the World Series — worth it.
You can go on the Wrigleyville Detour — and a host of others in the Chicago area — by downloading the app. Until then, go Cubs.
See the world from your inbox.
Sign up for The Journey, our Travel newsletter.