Growing up in Chicago, there was nothing that compared to the summertime. Outside of the obvious warmer weather and lack of school. There were festivals to go to and beautiful architecture to admire from all sides. I am biased in my love for the city, but for me, there’s no place else I’d rather be from. Don’t get me wrong, there were dangers to overcome, violence to navigate, and a lack of air conditioning units in my neighborhood, but that all contributed to making me the person I am today. If you’ve never been before, summertime in Chicago is an entire vibe and a half. There were two pivotal summers for me, 1995 and 1999.

1995
In 1995 I graduated from 8th grade and what followed my commencement ceremony was at that time, the hottest summer Chicago ever recorded. With that heat came a whole lot of outside time or driving around with the A/C on. The entire city was outside one way or another. I feel sad that today’s kids are not able to experience what life was like before cell phones and widespread internet. Of course, being 14 years old at the time, I felt like I was almost grown, and since I had so many relatives in the area, I stayed outside until well after the streetlights came on. They used to say the only things open after midnight were legs and hospitals. Not for a lack of trying, the only thing I could vouch for were hospitals.
The summer was brutally hot yet somehow, I managed to survive most of it on Chicago Park District water fountains and oversized freeze pops from the local corner stores. There were a couple of block parties where they close off a block or two for a whole day and the grownups would make hotdogs and hamburgers, while kids played in the streets. Chicago house music or what seemed like a Frankie Beverly inspired playlist could be heard on speakers throughout the city, turned up to the point of distortion. 28 years later and I can still picture that summer.
Eventually I think Chicago will be the most beautiful great city left in the world
Frank Lloyd Wright
Quick Trip
My brother graduated high school a week after I graduated from 8th grade. My mother and I had the unique pleasure to travel by Greyhound Bus from Chicago to Hampton, VA for his graduation. I was excited about it until we made it to Gary, Indiana when one of the other riders decided to smoke a little crack as if no one would notice. We ended up pulling over and that guy was escorted off by the authorities. Considering Greyhound bus stations in major cities were essentially spruced up Port O John’s with busses, his drug usage shouldn’t surprise anyone. We arrived in Hampton about 22 hours later and had a decent time for being in Hampton Virginia. No offense to Hampton, but the summer wouldn’t have been as amazing down there. My brother and I had a great time that summer, which was cool because I only saw him for a grand total of 3 weeks combined between 1996 and 2008. All but 4 of those days occurring in 1996.

Upon returning to Chicago, I got a new pair of shoes, some green, canvas Nike Air Darwins. I may have worn them 5 or 6 times before they were ruined. Basically, the first week of having them. One very hot evening, my mother kept pressuring my uncle to get an Italian beef even though it started raining like crazy outside. After about an hour of pressure he agreed, and I just decided to tag along for the ride. As we’re driving, rain pouring, we approach a flooded viaduct, but my uncle couldn’t tell it was flooded. He was driving slow enough to not make a bad decision, but he made the bad decision to proceed forward anyway. Once he realized his error, he quickly let the windows down. We made it about 20 feet before the car completely died. Seconds later it began to fill with water. Yup, we had to climb out of the windows and wade through it, my shoes were ruined and so was that Camry.
1999
In 1999 I graduated from high school with a 2.3 GPA and no real desire to attend college, but also no good ideas of what to do with my life either. I still applied because gap years weren’t a thing for people that actually went to college. I spent the summer of 1999 driving around the city in my tiny blue Ford Festiva getting into all kinds of stuff. A little trouble, a little action, a little entertainment. I was working at Allstate too. This afforded me the ability to be everywhere because my parents weren’t just giving me money to do this random stuff. With all of this freedom, a fuel-efficient car and relatives that rode the bus, I gave a lot of rides. I remember hanging out one evening and making pretty good progress with a young lady, but when I offered her a ride home in what my cousin Mike called “the fruit basket” she declined and opted to take the bus instead. I had better luck with girls on public transportation than I did in my car, but I would rather roll solo than deal with CTA.
Unfortunately, I wasn’t rolling solo that often. My cousin Mike was freshly out of jail for the second time, so I told his mom that if he hung out with me, I’d do my best to keep him out. It’s not like he was suddenly making better decisions, I was there with a front row view into how poorly his decision-making skills were. The only difference was I was there to run interference and or veto his harebrained ideas…until his mom bought him a car. It was all downhill from there for him, but that’s a completely separate story for him to tell one day. As for mine, we were constantly riding through the city, and he was a good luck charm for me. A few of the girls he was talking to, turned their attention to me instead and he was always cool with it. To an extent, it was manipulative. Once he found out that these girls liked me, he’d use their desire to hang out with me to get $10 or $20 to relieve them of this 3rd wheel disrupter. I was totally onboard because I was an 18-year-old boy of course. Win-Win!


I adore Chicago, it is the pulse of America
Sarah Bernhardt
Not All Good
With any series of high points comes low points, the balance of life. On one particular day, Monday July 5th to be exact, I had plans to continue my winning streak. I went to pick up a young lady I went to high school with from work, her dad was out of town, and we were planning to head back to her place. She worked at a grocery, so when I arrived, I picked up a juice and some gum and went to her line to let her know I was there and where I parked. Every time I went there before that, she gave me an employee discount and today was no different. The total bill for the juice was less than 2 dollars normally, I paid $0.79 or $0.89 for it, I gave her a dollar and said keep the change, took my receipt, and headed out the door. I threw the receipt in the trash can on my way to the car and began opening the drink when the security guard stopped me. I resealed it as he asked if I paid for it. I said yeah and he requested to see the receipt, which I refused to get from the trash, but I let him know we can prove it by going to the lane I bought it from. This is where things go left.
We go back in the store, but instead of heading to the lanes, he ushered me to the basement of this grocery store. I repeatedly told him which lane I went to, and he began telling me I was going to jail for stealing. Then he cuffed one arm to the table, and my other arm to the chair. The first question most people have is “why did you comply” and the answer to that is because I knew I didn’t do it, so I assumed it would get rectified. What actually happened though, is this guy sat across from me constantly threatening me and saying he’s going to wait until the holding cells close so the cops will have to take me to cook county and I’ll be there until the morning. I requested to see the manager, he just sat there laughing saying I wasn’t tough. The manager finally came, but said it was the security guard’s decision to press charges. After about an hour in this basement, he called the police.
At this point I assume it’s a scared straight moment, but nope. The cops arrived and they first asked “why is he cuffed like this” the security guard said it was to ensure I didn’t run away, but I went in voluntarily to solve it, so he was full of shit. They uncuffed me and took our statements. At this point, they let me know that they had no choice but to take me in, though they disagreed with the decision. I had on some khaki shorts and a red short sleave button up shirt, with a tank tee (wife beater) underneath. When the cops cuffed me to take me away, he pulled my shirt back to it was all the way off my shoulders, then he took a polaroid picture and said I was no longer allowed to come to the store…as if I would return after this terrible customer service moment.
Good Cops, Bad Security Guard
The cops were friendly, they said they could avoid taking me to county, but they had to wait for their guy to start at the holding cell nearby. As a result, I had to ride with them for a few hours. When I got there, they processed me in, and that guy was really cool too. We chatted about what happened, and his first question was, “was the security guard Black” I said yeah, and he dropped his head. He initially put me in a cell with this guy screaming about needing his meds. That lasted for about 30 minutes, when he came back to give us both bologna and white bread, I told him we were gonna end up fighting, so he moved me to a darker, shittier cell by myself. As I sat there on the cold, metal bunk a couple of rats ran by the toilet. During the entire ordeal I was worried about what my parents would say first, if the young lady made it home, if I’d be able to wake up on time for work the next day. I never really thought of it as something that could be bad for me.
When my parents picked me up, I tried to make light of the situation, but it was like 12:30 am and they weren’t really in the mood for that. They listened to the abridged, 18 year old pride side of my story, but I could tell they were skeptical of my actual innocence. I made it to work on time the next morning and the whole time I walked around as if everyone knew what happened. Being a Black kid in an office filled with older White adults, I didn’t think they’d understand, but I told them anyway to avoid any surprise “walk this guy outta here” moments at work. They didn’t fire me though, they felt sorry for me and gave me more work to do. All in all it was a good summer, I learned and experienced a lot. 1999 was the last full year that I spent in Chicago and I definitely got my money’s worth with the highs and lows. Til next time!
Great life story. It never ceases to amaze me how many young Black men get caught up like your 1999 experience by other Black men trying to prove their own manhood!