Being from Muncie, once labeled “Little Chicago” for the mobsters that would hang out there in the 1920s and 1830s due to it’s proximity to the “City of Big Shoulders” yet also because of its distance from it, I would visit the “Windy City” from time to time during the warmer months. It wasn’t until 1988, long after moving to Texas, that I experienced the winter months there.

Around 1980 I made a couple of business trips to “Chi-town”, once for a two-week assignment by my boss, which entailed conducting inventory of hardware stores in various locales around the city, including the Italian neighborhood of Cicero (the locals cursing each other in Latin were very audible through their open windows), and another to deliver an automobile to a buyer. There were also a few pleasure trips, usually during the summer Jazz Festivals at the Navy Pier.

I took my girlfriend Jayne along on the excursion to deliver the car and accompany me on the short flight back. It was just after dusk when we crossed the Gary city limits on I90 westbound and as I was describing the notorious reputation of the city, she expressed an urgent need to use the bathroom.

We pulled into a near downtown fast-food place so she could do her thing. We also grabbed a couple of sandwiches and soft drinks for the road and driving out of the restaurant, were promptly pulled over by a Gary police officer. He asked for my license and the nature of our business. I explained that we were heading to Chicago and stopped in the city to use the facilities and that we were wending our way back to the interstate. He said to follow him, that he would escort us back to the interstate because our “lives were in jeopardy”, probably due to the nice vehicle we were in, our skin color and possibly because of my girlfriend. Fortunately, that was the only dramatic incident of the trip.

After graduation in 1983, I moved to Dallas and went to work as a software developer. My third professional position out of college was as a Management Consultant with Peat, Marwick, Mitchell & Co., a highly esteemed accounting and consulting firm with offices around the globe.

Just a few weeks after the passing of my Mother on Christmas Eve of 1987, I was assigned to a 3-month project in Chicago. It was a pilot project for Mountain Bell Telephone involving the use of some CASE development tools by our own Catalyst Group, a technology division of our firm, to convert legacy billing systems from Assembler language to COBOL/CICS. The arrangement allowed me to return home to Dallas every 2 weeks and to visit my hometown every other weekend so as to console with the remainder of my family there.

I departed for the project when Max Kyle gave me a lift to DFW airport during halftime of Super Bowl XXII, which we were watching on Dave Clark’s big-screen TV out on his back patio as the temperatures were in the mid to high 70s. Early in the 2 hour flight, I heard that Doug Williams, the quarterback for the Redskins, was leading a major comeback which resulted in a Washington victory over the Broncos. On arrival at O’Hare, the temperature was below zero with a wind chill factor in the minus twenties.

I booked into a suite on an upper-level floor of the Executive on East Wacker Drive, a couple of blocks from Peat Marwick Plaza where the project was to be conducted. The suite consisted of a king size bed, a full living room, dinette area with fully stocked service bar, and an awesome view of the IBM Center (the 2 towers that look like stacks of plates), Chicago Tribune (the original Pizzeria Uno on the ground level) and up North Michigan Avenue (The Magnificent Mile) directly across the river. I could see the historic Water Tower and the beautiful old Radisson Hotel where Dad, Sharon, Kim and I once stayed while visiting to do some shopping at Water Tower Place mall and take in some of the greatest food on the planet. I was enlightened to my favorite Italian restaurant on that trip when we dined at Corona’s on Rush Street.

On my dresser was a fruit basket and a bottle of fine wine with 2 wine glasses, compliments of the hotel staff. I remember thinking how sad it was that I didn’t have my ex-wife Nikki with me to appreciate it with since we’d divorced the year before.

After settling into the room, I proceeded to the hotel lounge where a fairly sophisticated “Pro” propositioned me. I told her that I was not a player but was curious as to her profession. We chatted for a short time and she showed me her credit card slider machine which she carried in her purse. About that time, a hotel manager told her she must leave and that he was tired of having to repeatedly ask her to leave the guests alone. Going back up to my room, I noticed a kiosk on one of the floors that sold porno mags and I remember thinking that the hotel manager probably only asked the “lady of the evening” to leave the establishment because he hadn’t gotten paid. Welcome to the real Chicago!

One of my hiring managers, Bruce Goldblatt, had arrived from Dallas on a later flight and was also staying at the hotel. We met for breakfast early the next morning at the hotel restaurant where we were to meet the project manager John Hays. Hays was already there at a table across the dining room, though we didn’t know it was him until he said something to us after about ten or fifteen minutes. He mentioned that it seemed to be a bad omen for the project because of our awkward introduction.

After discussing the project details over breakfast, the three of us walked down the street to Peat Marwick Plaza. When we first walked out the front door of the hotel, the snow was coming down at a 45-degree angle and I had yet to adjust to the drastic climate change. I hurriedly walked to the corner of the building to gain some cover from the blowing snow only to discover it blowing sideways. No wonder they call it the “Windy City”. Fortunately, I discovered the tunnel system that day which allowed a sheltered route to and from work after that, though when people opened the doors to the parking garages, it sent a shivering blast through the corridor.

The project started with an introduction of the team members, an overview of our objectives and a description of our deliverables. It was a relatively small team of about 7 or 8 of us, but very sound technically, as each person had their unique area of expertise. Mine was a working knowledge of Assembler language and billing systems.

During the work week, our team would venture out to lunch daily. Several times we went to Bennigan’s on State Street, their busiest store in the country at the time, and one day, we visited Gino’s East, where everything was covered in graffiti, from the pizza pan and spatula to the beer pitchers, of which my boss had 2 by himself. He was a big man. I believe Gino’s had the best deep-dish pizza I’ve ever put in my mouth.

The tunnel system mall provided many places to go to avoid the bitter cold outside. One of my haunts was a Morton’s of Chicago where a couple of my teammates and I would frequent after work for the happy hour buffet and discuss the project, among other things. One night, I struck up a conversation with a very attractive oriental gal who told me she lived in Chicago’s China Town. I call Chicago “the world’s biggest small town” because it is actually a conglomeration of ethnic areas, each like its own town and the Chinese area is one of them. Not long after meeting that lady, I noticed her picture on the cover of a local magazine with its caption reading “Miss Chinatown 1988”.

When going to and from the airport, one of the busiest in the world, I would take the “L” train which went directly to the loop in the vicinity of my hotel. It was rickety but felt safer than riding in a cab. The cab drivers there are absolutely insane. Nothing worse than taking a cab on the Dan Ryan Expressway, especially when parts of it are under construction, which is all of the time.

As I was getting into my routine, I discovered a Bally’s Fitness Center in one of the towers along my daily tunnel route. This multi-level Bally’s, of which I was a lifetime member, had the men’s locker room on the top level and the Stairmaster on the bottom level. One of my favorite exercise contraptions was the Stairmaster, because you could read or listen to your walkman, while elevating your heart rate for the right reasons. On my first visit, I went to the Stairmaster on the lowest level after having a fairly good circuit routine on the nautilus machines on the upper floors. At the completion of my workout on the Stairmaster, I realized that I could not climb the stairs because my legs were completely spent. There was no elevator. I eventually pulled myself up to the shower room using the hand-rails after about a 45 minutes struggle. Needless to say, it was several days before I ventured back to the club.

There was a quaint pizza joint next door to the hotel. It wasn’t Gino’s, but it was good enough and the atmosphere was cozy. I would eat dinner there fairly regularly, a couple of times with Bruce. I remember sitting in there watching Roberto Tomba win the men’s downhill at the Winter Olympics in Calgary.

The project was conducted on an upper-level floor in a large room with a view of the Lake to the east. There were a couple of blocks between our tower and the shore, which were all under construction but not far enough along to obstruct the view. You could see up and down Lake Shore Drive, boasting the world’s most expensive living quarters, and the Navy Pier extending out into the lake on the north side of the mouth of the river. Everything between Michigan Avenue and the lake is built on top of the rubble of the “Great Chicago Fire”, the only structure to survive the fire is the old Water Tower. One extremely cold morning early in the project, I looked out across Lake Michigan to actually see the frozen mass slowing moving out into the water. The view was stunning from that vantage point, though you could not see Michigan on the opposite side (you probably could from a higher point) but you could clearly see Calumet City down to the south, which is basically the Indiana state line.

All of us from the project piled into a cab to Rush and Division Streets one Friday night before a weekend that I was staying in town to attend an office party being hosted by one of the gals in the office. We hit all the spots, starting with PT Chicago, working our way down to Mother’s and Butch McGuire’s, then back along the spots across the street. One by one, my pals would catch the last train out to their particular suburb and by the time I was at The Snuggery, my last stop, it was just me. The line to get in was long, and when it was my turn to go in, the doorman said it appeared that I’d had a few and should go back to the end of the line. So I did, and by the time I filed to the door again, the cold air had done me some good, the doorman was cool and I was thirsty. I met a friendly couple in the crowded back area who kept buying me shots of Tequila (I already had a few of those compliments of some fellow Texans I’d run into at Mother’s), and I remember getting a little sentimental and perhaps shedding a tear or two as I told them that I had recently lost my Mom. The next thing I know, I’m “coming to” on my hotel bed, fully clothed with my overcoat on, briefcase still in hand, chocolate mints laying next to my head on the pillow of the still made bed, with just enough cash missing from my wallet to pay for cab fare. Wow! I had gotten far more than a little “drunkypoo”. It was the worst hangover of my life to this day and will remain so.

I never made it to the party due to my self-induced influenza but was feeling somewhat better by Sunday night when I was to meet with one of the guys from the office at a club on Lincoln Avenue. I didn’t know him well, but he was a young guy that just hired in under Tom Bloomquist, another of my hiring managers that had recently transferred to Catalyst Group. I once again hailed a taxi and followed the written instructions to the destination. When we arrived at the address, I thought there’d been a foul-up. It appeared to be nothing but dark, eerie, vacant warehouses and abandoned office buildings. I remember seeing the “L” passing overhead many blocks down the street to the west and thinking that it was the only visible sign of life in the entire area. I told the driver to stay until I signaled him to leave while I went to the door of the place and checked it out. When I walked inside, I was amazed to see that it was packed with people wall to wall with a thirty or so piece jazz band in a band pit. It was like a speak easy from the prohibition era. I waved the driver on.

My young cohort bought tequila shots (“hair of the dog” works but is not recommended) for all of us at the table which included some pretty hot young babes and I was starting to feel human again. I finally decided to go back to the hotel and get some more rest before the start of a new work week. When I arrived at the office the next morning, that guy was already there, all bright and chipper, saying he’d already been there for an hour after playing racquetball at five o’clock AM. Here it was, him living in the suburbs and me only a couple of blocks away through a carpeted tunnel and I was beat getting into the office by hours. Sheesh! I gained an immense deal of respect for that guy’s stamina, realizing then and there that I was no longer a youngster and could not even begin to try to keep pace with him or his kind. And I was only 28 years old!

It could get lonely downtown at night. After regular business hours during the week, the sidewalks seem to roll up and the entire downtown area dies. One night when it was a little warmer than it had been, I ventured down Lower Wacker under Michigan Avenue which was so dark and eerie that I soon turned around and walked back. There is a whole network of streets below street level down there, like a city under a city. There was very little to do, but I did manage to find a small joint not far from the hotel that served decent food and had a three-piece jazz combo. It was a mellow place with its clientele consisting of local residents who lived in the nearby high-rise condos.

The original Marshall Field’s, my favorite department store, was a couple of blocks away and took up an entire block. It devoted an entire floor to men’s clothing where I bought a London Fog trench coat and rubber galoshes to help save my leather shoes from the salt water slush of the Chicago streets.

By the end of March, it was beginning to thaw a little, though it was still incredibly cold and windy. It seemed that I constantly had a raw throat and stopped-up nose. John Hays, the Project Manager, recommended Alka-Seltzer Plus, which was so effective for me that I used it for years to come until learning that the acetaminophen in it was harmful to the liver and mine was already under siege.

One quiet evening near the end of the project, I was sitting at a table by a window in the hotel lounge, watching the soft street lights glowing through the snow blowing over the old fountain out front with its ancient statue of a naked angel. I was still thinking about the loss of Mom and Kim, reflecting on the city and how it had been such a major part of much of my family that had passed on. I believed that night that I had actually started the healing process, but then again, sometimes I wonder if I’ve ever healed at all – even to this day.

On my final flight back to DFW, I sat next to a very personable black guy. We got to talking and I told him that I was glad that my commute from Dallas to Chicago and back every couple of weeks was finally over, when he told me that he made the same commute daily. He was radio personality Tom Joyner, now syndicated, who had a morning show in Dallas and an afternoon show in Chicago, every day!

That May, I was invited to the Indy 500 with only a week to arrange the logistics, which are nearly impossible when it comes to getting to Indianapolis on Memorial Day weekend at a moments notice. I ended up flying into O’Hare once again and staying with my friend George Smedinghoff who lived nearby. George was a mathematical genius who was an Actuary for Hewitt Associates. It turned out to be the last time I saw him. The next morning, I rented a car back to the airport and rode the “L” downtown to Grand Central Station. After trying to figure out what to do next, I ended up taking a bus to Indianapolis. Downtown Chicago was like a furnace, even more so than in Dallas, and it had been only little more than a month since I left the place in its semi-frozen condition!

When I finally arrived in Indy, the downtown area was cordoned off forcing me to take a horse-drawn carriage to the outer area where I hailed a taxi to get to Dad’s house in Broad Ripple. I ended up staying with my buddy, Kent Haney, the night before the race.

We made it to the race and had a good time and I’m glad I went and all, but was anxious to get back home. I took a flight out of Muncie on a commuter flight to O’Hare in time to catch my AA flight back to DFW but the plane had a mechanical problem and was canceled. It was the last flight of the day and the airport closes at 11:00 pm. Fortunately, I was a member of the Ambassador’s Club and an AA frequent flyer so they put me up at the airport Marriott and got me on the first flight in the morning. When I arrived back in Dallas early the next morning, I went straight to work with bags in hand. When the folks asked how my weekend at the race went, I simply said “no comment”. The year 1988 turned out to be the lousiest year of my life to date, but the very next year, everything improved significantly – only way too fast! More on that later …