Life’s Lessons as Learned in a Cab!

Through the Windshield, Life as seen from a Cab. Part 1

When this story hit 20 pages and wasn’t even near done I thought it a good idea to offer it in installments.


Chicago at night near historic Chicago water-tower

                Back in the mid-nineties I drove a cab for a living. It was an interesting experience to say the least. It was an experience that had a lasting influence on my life. If you read my post on cab etiquette then you already know how it was I came to driving a cab and the slang typically used by drivers, so I won’t go into it here (I know shameless plug…). When I first took the job I wasn’t too sure what to expect I was just hoping to make a little money and keep my head above water. What I got from the experience is a life time of interesting stories and new perspectives on life.

The company I signed on to as a sub-contracted driver had an extensive driver training plan, a whole hour instruction on the cabs computer then a ride around with a driver for a couple of hours. My first epiphany came when I realized is that I didn’t know the city or surrounding suburbs nearly so well as I thought, but I had a six county atlas with me and other maps so I figured I’d be ok. For the most part I was except it became clear early on that although the maps were definitely handy when trying to find streets it took too long if you stopped and looked too often . So I started a process of learning the locations of the towns and driving to them using the stops along the way to spot read the maps until I found my street and the address for pick up.  The suburbs usually don’t have too many people flagging so almost all calls during a shift came from either the dispatch or a walk up if you were waiting at a cab stand.  During my “learning period” driving the cab I talked to other drivers getting tips and pointers from them on where the best spots where and when to be there at the best times for customers. They also gave advice, really good advice that served me well on many occasions while driving, after I got a feel for what I was doing my own streetwise kicked in and I improved on making money and staying out of trouble.

Drivers can be very cliquish so you tend to hang out with the same group of people when time arises I had many driver friends during that time guys like Whitey & Nash and a woman named Marie.Whitey got into the business after the company he worked for as a warehouse manager closed and he was unable to find other employment. Nash was a security guard and limousine driver that after an injury had to give up the security work so he supplemented limo driving with the cab.  The two were quite a pair sadly I don’t see them anymore I really enjoyed our chats while at the cab stands. Nash the last I heard eventually moved his family to Florida to pursue a better job offer and Whitey who thought life couldn’t get any worse had his wife divorce him and his kids stop talking to him. I’m not sure why his kids stopped talking to him, I never asked beyond finding out that his wife couldn’t take anymore of the long hours he spent driving and time he spent drinking after work.  Marie as far as I know had been a cab driver for many years, in fact when I first started her daughter also drove while going to college studying to be an emergency medical technician or EMT.  Marie is a tough old gal who like Whitey, Nash and I drove the night shift. We all started between four and six pm and Whitey, Marie and I would drive until the morning airport runs were done, usually nine or ten a.m. Nash usually quit after the bars closed in Forest Park between two and three am. Yes those were long hours but one can generally take a break as needed unless it’s busy then you tend not to notice the long hours.

The clientèle whether person and package all come with their own story, in most cases it’s all pretty mundane go there pick them up take them to their destination drop them off and get paid.  However there is a whole group of passengers whose stories are not in the mundane and some of which are down-right tragic. When you work over-nights you generally get a healthy share of them, for example.

Sue was a regular rider she originally when started she taking cabs it was to her job, she worked as a nurse in one of the local hospitals. She was young, pretty, and full of life, she frequently carried on friendly and extensive conversations with the drivers and was generally regarded as a good trip. Sue usually took the cab to and from work, but as time progressed Sue started using the cab for other purposes.

Sue was in the throes of what would become a serious drug problem. In the beginning she would only ask the drivers for round trips into known drug areas on her days off but as time went on she started working less and less and using more and more. It wasn’t long before her money started running out and she began using the one asset women have to make money, sex. Sue went from the vital effervescent young woman to a drug using whore. It didn’t happen all at once. It was a gradual thing slowly taking away her vitality, personally, and beauty. The drivers witnessed the slow and agonizing decent of this unfortunate woman. In response many of them stopped taking her to the drug areas and would only take her to and from work or not at all.

However, as in all walks of life there are the opportunists that would still take her providing she paid for the ride with sex which by that point she was more than happy to provide as long as she was able to get her fix.  I was one of the ones who would only take her to and from work and stopped taking her after her change in employment. Last time I saw her she looked haggard, worn-out, and many years older than her actual age, she was standing on street corner flagging cabs, because the company much to their credit had stopped taking her calls after they became aware of what was going on.  Personally, I never took people on drug runs. Watching Sue only re-enforced my personal belief in not doing them or drugs for that matter.

Although you might at first think that Sue was an isolated incident she wasn’t. There was another woman named Cookie who would also satisfy the drivers urges for a cab ride, sometimes for drugs sometimes for a trip to the grocery store. She was the girl friend of one of the drivers named Johnny. Nicest guy you’d ever meet when he came into work but after he and Cookie had been partying he could turn aggressive even violent after he’d been drinking, especially if he thought you might have benefited from one of Cookie’s special cab rides.  Johnny didn’t share Cookies love for the drugs he was a drinker when he wasn’t working. He and Cookie were well known for their out of control parties, many of which ended with someone getting arrested or at the very least the police being called. When he was working he was a great driver customers described him as friendly, helpful and generally pleasant in the cab. He worked long hours and drove like a madman but while he was working he stayed out of trouble.  Johnny sadly passed away a couple of years after I got out of the cab business, he drank himself to death. Cookie found him on the couch the morning after one of their infamous drug & booze parties. He wasn’t even forty years old. Cookie though initially devastated by his death recovered quickly and was soon shacking up with another driver.  Back to her old routine of offering special rides to drivers.  I guess you could say she was a cab groupie and believe it or not cab drivers actually do have them.

Then there was Ms. Smith. Out of all my time driving she was perhaps one of the most outrageous passengers and definitely a cab groupie. Ms. Smith was an older woman probably in her late fifties early sixties when I first encountered her. I had a pick up at an upscale Oak Park home, I pulled up she came out with some assistance from the residents of the house which explained she had a bit too much to drink and needed to go home. She lived in one of Oak Park’s ritzier condominiums near the mall. She was a very touchy feely kind of a person who would constantly touching the drivers while they were driving and would break into singing opera at the drop of a hat. So there I am with her in the cab fortunately it was a short trip. Gaging from the amount of assistance she needed getting into the car I wasn’t surprised when she asked for help getting to her condo, so I gave her a hand getting to her unit. She asked me in for a coke since I had been so nice helping her get to her unit. So I said OK, I was planning on getting a drink after I dropped her off so I thought “Why not let her buy.” At first everything seemed normal enough she had a great unit twelve flours above the street and while I was sitting in her living room drinking my coke, I enjoyed the great view of Oak Park and River Forest that her unit had.

It was after she disappeared into the bedroom that things took a turn to the strange. She appeared after only a minute or two wearing nothing but lingerie. She switched on her stereo and started singing opera again while dancing around the room. Normally this type of behavior given her age might have freaked me out a bit, but I had been chatting with Whitey when I got the call and he warned about her eccentricities.  So though I found it a bit disturbing that her clothes weren’t a bit more opaque, I watched her dance around the room and complimented her on her singing, which actually wasn’t bad, and I also complimented her dancing. The rumor amongst the drivers was that she had always wanted to be a ballerina or an opera singer but something prevented her from pursuing that career. Either her family didn’t approve or she just wasn’t good enough or she got married and her husband didn’t approve.  The end result being she was at a point in her life where now she could be the person she wanted to be and she was. Though I gave her many rides and had many laughs with her, I only ever went into her apartment the one time. Whitey had also told me that once she gets to know you all of her performances ended with you getting a happy ending. I was twenty six at the time and a sixty year old woman wasn’t where I had my sites set.

Molly on the other hand was in her late thirties or early forties and much easier on the eyes. Molly was another groupie, from a rich family out of state who apparently was paying her to stay in Illinois. She has a condo in River Forest which is a very ritzy town.  I guess you could say she was like a modern day remittance man/woman in the Victorian sense. She also had a reputation of being a wild child. Some of the drivers claim to have been with her and her reputation around the bars was well known. She also seemed to have a preference for older men, but then again she was often in the company of younger ones too.  She definitely had an east coast accent in any case. Even when sober Molly frequently took cab rides since she had no car which was probably a good thing. A lot of the guys knew her. She also frequently had male companions with her though rarely the guy would be accompanying her more than once.

One night I was out on the town making my way through the bars in Forest Park, the usual stuff, drinking, chatting with friends. After a while the area bars started to close. I wasn’t feeling particularly ready to call it a night so I jumped in a cab and headed over to Cicero when the bars have a much later license. Cicero was a bit on the seedier side in those days, seedier if you consider strip club/brothels seedy. Almost all the bars had security late at night it didn’t matter what they offered, they all had security. So I decide to hit this bar called Murphy’s, a quiet place except for the occasional bar fight. Their security was pretty good, even polite at times and the clientèle was generally late-night folks looking for a few drinks before heading home.  So after getting buzzed in I took a look around the bar and there was Molly sitting by herself in the corner, drinking and smoking.  She had spotted me before I saw her and was waving me over.

I walked over and said “Molly, how ya doin? What brings ya to this late joint?” “I came here with a guy to have a few drinks, we ran into someone I knew a fight started and they were both thrown out.” “How’s your Grandma?” she asked.  I had actually met Molly years before I started driving a cab, The first time I picked her up she swore she knew me but couldn’t remember where from, I told her she looked familiar too but it wasn’t until I had gotten her home that I made the connection as to how I knew her. My Grandmother and Great Aunt had the condo above hers and I had met her a few times when she had stopped up to chat with them, by this time though they had both been moved to a nursing home.

So we sat there in the bar awhile chatting she told me about her wild days and how her family was a bunch of tight asses who sent her to Illinois where a family friend was supposed to help her straighten out her life.  Instead she started sleeping with him at first out of revenge for the rejection of her family then out of habit, finally he broke it off with her after his wife started to suspect something more tawdry was going on.  So she got drunk and told his wife what going on, according to her it was one of her few regrets.   After drinking at the bar for a bit she suggested we get out of there, we could go back to her place for a nightcap. I had the bartender call a cab.  We left the bar and waited outside for the cab.

While we were waiting Molly and I flirted with each other it was thankfully a short wait for the cab to arrive. One of the perks of being a driver is that the cab company & other drivers make you a priority when you need a cab. The driver was one of the guys I knew, but not too well, he was a day driver who was just starting out.  Molly knew him too so it was fun conversations and joking around until we got back to her place.  Soon we were back at her place, I paid the driver for the ride and we wandered our way through the parking lot and grounds of the complex back to her place, actually it was more of a controlled stumble as the effects of all the alcohol were kicking in. When we finally got into her place, we decided to switch to iced tea and got comfortable on her couch her apartment was nicely appointed and extremely clean. We talked about music and our favorite bands and like but soon the conversation turned into other evening activities.

It was late morning when we finally arose and after some morning activities we showered had a light breakfast and decided to go to a bar. I called a called a cab, the dispatcher sounded surprised that I was still at Mollies. I was surprised he even knew I was there to begin with. Apparently, spending the night with her wasn’t unusual but being there after twelve was. Molly and I went to a bar in Forest Park that I usually hung out at, she was meeting a friend there and they were going out and about for the afternoon. We sipped a couple of beers and played some darts, soon her friend was there and we bid our goodbyes. I grabbed a cab and finally headed for home.

After a long nap I went into work, I have to say the reaction I got from people at the company was surprising. The guys weren’t so shocked that I spent the night her as much as I was still there and running around her the next day. Needless to say cab drivers are notorious gossips. I Molly and I hung out off and on for a bit but nothing serious.  Last I heard she had finally settled down with some guy, but how settled is anybody’s guess.

As a driver we also drove around a lot of call girls, sometimes they were outrageous like this girl Judy I picked up in Berwyn. She was visiting her boyfriend who couldn’t leave his apartment because he was on home monitoring, that’s a nice way of saying he house arrest. He wore an ankle-bracelet that had a transmitter in it that was licked to a receiver located in his apartment it limited his ability to leave his residence and couldn’t be removed without setting off alarms. As I pulled up at the address he was standing at the corner of the building and waved me over. Judy came down shortly she was young skinny brunette wearing a black mini-dress, fishnet stockings and ridiculously high, high-heels the kind that you were just waiting for her to turn her ankles in.  She navigated the parking like she was wearing gyms shoes, hopped into the back of the cab and we were off to a swanky downtown hotel. At first she was fidgeting in the back seat putting the finishing touches on her makeup and adjusting her clothes for maximum effect.

We were making small talk when she finally blurted out “Let me ask you something?” I said “OK, ask anything you like I don’t know if I’ll have an answer for you, but I’ll try.” So she asks “Why do poor guys f… like madmen and rich guys can’t get it up?” I have to admit her question caught me off guard at first, and I stammered and chuckled out a quick “That’s a good question”  “I suppose it might have something to do with the rich guys are more concerned with making money and flashy shows of their wealth instead of taking care of anyone other than themselves. “ she sat there quietly for a couple of seconds and then she said “I mean my boyfriend is an ass who is always getting  into some kind of trouble, but he can f… all night long and he’s great at it. Most of these guys I visit want me to do all kinds of weird stuff and most of them have a hard time staying hard. I mean they want to, they just don’t seem to be able to.”  I replied “Well, not being a rich guy I don’t actually know why.”  “But I’ll be honest it can’t be that they don’t find you attractive, you’re a very pretty young lady.” And that she was. She was very gracious about the compliment and the conversation for the rest of the ride we talked about her being a call-girl, she didn’t like the term prostitute, she put in the same category as hooker she thought it only for girls who walked the street. She would never do that. She also thought that the name implied she had a pimp which she didn’t. Before her boyfriend got busted he used to drive her around but he never got involved in her transactions. So for her, she was either a call-girl or an escort. When we finally got to her destination she paid for the ride with a generous tip. She asked me to wait ten minutes in case she or her client decided not to go through with it. I told her I would, in fact I was there almost thirty minutes waiting for a trip back out of the loop heading towards my companies home turf.

Another escort that used to ride with us occasionally was Ms. Anne, a very quiet and kind of mousey woman that at first you wouldn’t think of as an escort. She had impeccable manners dressed in evening formal whenever she went out.  She was pleasant to talk to and would tip well, she always asked the drivers to wait fifteen minutes for her in case her customer canceled after she got there. To that end she always paid meter and a half for the ride to assure that the drivers would wait, which most of us did. She was an attractive woman, not a stunning beauty but one who could definitely draw men to her if was sitting alone in a bar.  Generally, she would silently in the back of the cab and  only make  small talk until she got to know you, then she would make small talk and with small glimpses into her personal life.

One night I picked her up on three separate occasions each time she had been rejected and I brought her home. With each trip she opened up a bit more. Probably because she was feeling insecure with her self-image, I realized this after the second round trip when she spent most of the ride home murmuring to herself about getting rejected.  I dropped her off at her residence and as soon as I told dispatch I was clear they sent me back to her house to pick her up. The third trip she really began to open up. We laughed about her catching the same cab three times. I told her she kept calling back before I got out of the area, which was the truth. She told that she’d never had so many rejections in one night. I said something to her like “Some days sh.. just happens.”  or something to that effect. Her response seemed a bit out of character when she said “I’ve heard it happens but it’s always been the other women that it happens too.” I thought to myself “Wow, someone’s self confident.” But I didn’t say that to her. Instead I asked her “May I ask you a question? If it’s too personal just say so, I understand completely” For a second she wasn’t too sure how to respond, with a somewhat tenuous tone in her voice she said “Go ahead.” Escorts tend to be very private people, especially when they’re working.  I said to her “You seem to be a very classy lady, you dress great and seem to have way more education then would be required for what you do, so why do you do this?” She sat there quietly for a few minutes trying to figure out how she wanted to respond. I thought maybe I had asked too personal a question, but she finally spoke.

“My mom was a prostitute when I was a kid growing up, when I got older I went to school, even took some college courses. I still do from time to time, I want to be nurse someday, but now I like to party and this job allows me to do both.”  I was taken aback by the frank honesty of her answer. I was aware that mothers that prostitute do sometimes turn their daughters out, but I only thought that when that happened with hookers the daughters would be trapped into the lifestyle without much hope of getting out.  So I asked her; “So your mom turned you out?” “No!” she said, “She doesn’t even know what I do, she thinks I’m a waitress in a private club. I work for a service and only go to pre-arranged calls from out of town clients. It would kill her if she knew I was doing this.”” Sometimes like tonight, I wonder why I do this. But the service charges a base fee even if I’m rejected so I always make some money even when I don’t provide a service. It’s explained to the client when they book.”  It was my turn to be quiet for a minute and think about what she said. It explained why I had only been taking her to hotels, and why she was so quick to hand out extra cash for us to wait.

She also explained that it wasn’t as bad as people might think, her clients all use protection.  Once you get used to the idea of having sex with strangers it was OK, especially since she never figured on seeing them again unless they called the service and booked her again. She also said she did have some regulars that she would see when they were in Chicago and sex with them was easier because there she knew how they were most likely going to act and what they’d want to do. She even had customers who just took her out for the evening and no sex involved. She also said the service made it easier on her because they tried to screen out suspicious calls, i.e. the cops.  Using credit cards also made it safer because the cops didn’t generally use them. They always wanted you to come to the hotel and they would want to pay in cash.

We talked all the way to the hotel she was going to, it was near O’Hare airport and as she had on each respective trip she paid me and asked me to wait, which I did. I have to admit I felt kinda sorry for her when I saw her walking back to the cab. As much as she had opened up during the ride to the hotel I thought about how frustrating this must be for her. Normally women don’t rejection well when they don’t want to be rejected and she was on strike three.  When she got back into the cab she was very silent and said quietly “Take me home”

She sat quietly in the back seat not saying anything for the first few minutes of the trip. It wasn’t until I stopped at a light on Mannheim road that I realized she had been sobbing. I asked “Are you OK?” she replied “Yea, this has never happened to me before, I never get rejected this many times.” I tried to think of something to say to her, but what do you to an escort in these situations?  Don’t worry ma’am I’m sure you’ll make it all back tomorrow? So I sat there quietly and she said in a much happier tone “Don’t worry about it, I’m just being stupid.” To which I chuckled.  I did finally say to her “Guys get nervous about calling escorts, I’m sure they just got cold feet when faced with you standing there.” “Not because of you, just the whole situation over-whelmed them.”

On the ride home it was her turn, she asked me all kinds of questions about being a cab driver, did I see myself doing this in ten years or what did I want to do with my life if I didn’t want to drive a cab.  I answered her questions “no I wouldn’t still be driving a cab in ten years, I wasn’t sure what I’d be doing but I’ll be having fun with it, I see myself settling down at point but where that point is I don’t really know.“ When we were a couple of miles from her house she asked “So what time does your shift end?”  at first the comment caught me off-guard, I answered most likely I’ll be done by two or three. But I might end at midnight it’s been a decent night so far. “You like to get high?” she asked, by this point I could see where it was going. “No” I said; “but it’s cool if you do, I’m more of a beer drinker.” I don’t have a problem with it personally it’s just not my thing. She quieted down and didn’t ask any more questions. When we got back to her place she paid her fare and got out, I thought hmmm apparently I missed an opportunity,  she must have lost interest after she found out I didn’t smoke dope.

Then there was Keesha, I picked her up around ten p.m. she was an arranged fare, the customer providing the ride paid with a credit card and told the dispatcher she had the address. The card was good so the dispatcher put the order through and I got it. Keesha was an African American woman in her mid-forties, she was very polite in a gregarious sort of way and soon we were chatting up a storm on our way to her destination which was a fair distance from Oak Park where I picked her up. I found out that she was a call girl, she originally had a good job with one of the utility companies but she decided that she was tired of the long hours and office politics so she said screw it and thought she’d try her hand being a call girl. She liked sex, so why not get paid for it was her rationale. During our trip down the Illinois highway system I kept asking where we were get off she’d just say “I’ll know it when I see it.” Needless to say, with the Wisconsin boarder quickly approaching I felt confident she was about to get us lost. So I asked her; “Do you remember the name of the exit so I can keep an eye open for it?” We were coming on the last exit before entering Wisconsin at this point. “Town line or County line or some kind of line” she said laughing. “You must mean County Line” I said; “We just pasted it” as I eased the cab on to the last exit and proceeded towards the southbound entrance to back track to County Line Road.

It didn’t take us long and soon were in Arlington Heights where her customer lived. Thankfully I had my trusty atlas with me because once we got there she got confused as to how get to where he lived, fortunately she had his address. I had to go up to his apartment with her to have him sign the credit card slip. She thanked me for the ride and asked if she could request me in the future, I said sure thing, If I’m working they’ll send me.  Her customer answer the door in his underwear, he was a chunky, dumpy looking guy who seemed rather perturbed about her being so late. He signed the slip and I was off. As I walked down the hall she called out; “Did he tip you?” “Yes, thanks” I replied. He hadn’t and I wasn’t expecting one the fifty plus dollars the ride should have been turned into an eighty dollar ride because she had the address. When I got to town I swung by the dispatch to let them know what happen since I suspected trouble.

The next afternoon I went into work and sure enough they needed to see me in the office. The accountant Jane came out holding the credit card slip from the night before. “The customer called this morning protesting the charge on his card. He said eighty one dollars was too much for a ride from Oak Park to Arlington Heights. What happened?” I explained to Jane the events and that “The customer refused to give Bill (the dispatcher) a destination and would only say the passenger had the address and directions, so I went where she told me to go.” Jane had a puzzled look on her face so I added;”Ask Bill, he’ll tell you same thing.”  The secrecy is all because the passenger was a hooker.  At which point all activity in the office came to an abrupt halt. With the office full of women staring at me and Jane standing there drop jawed, I just shrugged my shoulders and said “It’s true.”  Jane stammered; “We already talked to Bill and just wanted to confirm this with you, we’ll handle it from here.” As I left the office the rapid whispering that was going on made me chuckle.

But life driving a cab isn’t all wild women and hookers there are many other strange things stories some sad, some happier, and some just plain weird.


Part 2 will follow shortly…. Stay Tuned!

About MartyW47

Attending Triton College. Studying Emergency Services Management & Criminal Justice. Currently employed @ MPPD & Aflac. After 30 years out of school I'm back in College and having a Blast!
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