Last week I had the pleasure of hanging out with one of Metro-North’s coolest conductors – Bobby McDonough, author of the blog Derailed. On the way to South Norwalk, and then back to Grand Central, we chatted about life, family, and of course trains. As he collected tickets, he almost thought he saw someone famous, but was mistaken. Bobby’s alter ego is the Conductor to the Stars, due to his many encounters with famous folks in his duty to the rails. In another era perhaps he would be a conductor on the 20th Century Limited, standing atop the red carpet as the rich and famous boarded the train. Alas, Bobby works the New Haven Line and his passengers range from Wall Street businessmen to sketchy characters and drug-dealers. Though he loves his job, it isn’t fun and games all the time – he’s even had his nose broken by a disgruntled passenger before.

I was pretty excited with the interview – as this is technically the first one I’ve done on the blog. I must thank Bobby for taking the time to answer my questions, and serve as my first interview “guinea pig.” Though the interview is a bit long, many of the stories Bobby tells are quite funny. And if you haven’t read his blog Derailed before, I definitely suggest it. Although Bobby has been busy and hasn’t updated it much, the archives go back several years and are filled with hilarious tales from the rails.

There are a lot of different types of conductors – some like trains, and others just see it as a job and a means to a paycheck. You mentioned growing up near the rails, and had family members that worked for the railroad – were you interested in the trains as a kid? Are you a little bit of a “train buff”?

No, I’m definitely not a train buff. In fact, when I was growing up, I was deathly afraid of the railroad tracks. I grew up six houses south of the tracks in West Haven, CT, and whenever a train went by, our house would shake. It was as if we lived on the San Andreas Fault. Guests would regularly hide in closets or stand under secure thresholds every time the Turbo Train went by.

My grandfather lived next door to me. He was a retired car inspector for The New York, New Haven and Hartford Railroad. He always warned me not to go anywhere near the tracks, and he’d frequently tell horror stories of kids getting their feet stuck in track switches. Trapped like wild animals, they’d ultimately get run over by express trains whose engineers were going so fast they couldn’t stop in time. As if to prove him right, shortly after one Papa’s warnings, a middle-aged neighbor was killed while crossing the tracks coming home from a bar late one summer night. A few months later, on a cold winter’s morning, I watched the railroad police as they searched the body of a neighborhood friend as his body lay frozen along the tracks at the end of our street. He was always doing crazy things, and I later learned that he’d climbed the catenary pole and innocently touched a high voltage wire. I guess my grandfather knew what he was talking about.

Though it isn’t nearly as true as it was in the past, there have been many “railroad families” – sons following in the footsteps of fathers and grandfathers in the service of the railroad. Since you had railroading family members, was this a career path that was encouraged for you and/or your siblings?

I’m a fourth generation railroad worker, so in the back of my mind, I guess I always considered a railroad career an option.

I shared a bedroom with my brother Brian who is eight years older than me.. He started as an fireman with Penn Central in 1974, and a short time later became a locomotive engineer for Conrail which eventually became Metro North. I knew firsthand what a railroaders life was like..i.e. getting called for work in the middle of the night, long hours, working seven days a week. I wasn’t sure I wanted that kind of lifestyle. I graduated college in 1985, and still didn’t know what I wanted to do with my life. Brian told me that Metro North was hiring, so I sent in a resume. A few months later I got hired as an asst conductor. At the time I thought a railroad career beneath me. After all… I was a college graduate. I told myself I’d only stay until a real job came along. That was 25 years ago….still here… and don’t regret it.

You mention that you got a job with the railroad “until a real job came along.” Was there a particular reason that you decided to stay?

I know it’s cliche to say, but I truly am a “people person,” and when you think about it, we carry some of the most fascinating people in the world. From the captains of industry, to Wall Street billionaires, Hollywood celebrities to street corner drug dealers (okay, maybe drug dealers aren’t fascinating, but they are interesting). Our passengers come from all walks of life, and I love to chatting with all of them and learning their life stories. Also, it’s a steady job with good pay and great benefits. I love my job… not many people can say that.

My favorite question to ask train conductors is “what is the craziest thing you’ve ever seen someone bring on a train?” The Wassaic portion of the Harlem Line has almost an “urban legend” that people bring their goats on the train. Have you seen anything nutty over on the New Haven Line?

One afternoon a guy got on in Bridgeport and had something hidden under his leather jacket. I watched as he sat down and pulled a baby bottle out of his front pocket. I assumed he had a small child inside his coat and was keeping him warm against the cold winter winds…I was wrong. When I approached to collect his ticket, a giant brown snout poked through his jacket zipper. I jumped back a step. “What’s THAT?” I shouted. He chuckled, unzipped his jacket and produced a Wallaby!!!! (as in a mini Kangaroo). I half expected him to reach inside the joey’s pouch and produce his ticket. “Where did you get that?” I asked. “I picked her up at Kennedy Airport last week” he said, as if everyone owns a exotic animals. “Is it even legal to own a wallaby?” I asked. “Yeah” he answered unconvincingly. (BTW, I just Googled it. Apparently it is legal).

As the “conductor to the stars” you’ve encountered quite a few famous faces while working the rails (though admittedly, I may be too young to recognize all of the names). Do you have a favorite, or most memorable, encounter with anybody famous?

In the early 1990’s, comedienne and ex-Saturday Night Live cast member Victoria Jackson used to ride my train on a regular basis. She is as sweet and wacky as she appears on TV, and I always got a big kick out of talking with her. Our conversations weren’t always light and funny though. Sometimes she’d confide in me about the messy divorce she was going through, once telling me her husband was evil. Other times she’d complain about not getting enough airtime on SNL. I felt bad for her, and sometimes I’d pitch skit ideas to her (she never used them).
One afternoon, Victoria generously offered to get me and my wife tickets to her show. I told her that we’d love to go but my wife was 8 months pregnant and we’d have to make it very soon. About a week later, Victoria called my home and told my wife that she had two tickets with our names on them waiting at NBC Studios. It was the last show of the season. I called her back and asked what time the show ended, and if I would have enough time to catch the last train back to New Haven (01:30AM). She arranged that we’d drive to Westport, then take the train to New York from there. She’d have her limo drive us back to Westport at the end of the night.

We did as she instructed and drove to Westport, then took the train into NYC. Just as she said, there were two tickets waiting for us at 30 Rock. The guest host that evening was John Goodman and Garth Brooks was the musical guest. We loved the show, but couldn’t help but notice that Victoria was never on stage during the entire show…not once. After the finale, we reported to the security guard as instructed and gave him our names. He called upstairs to her dressing room, then nodding his head in agreement, pointed us to a bank of elevators. When we stepped off the elevator , we immediately heard muffled sobs coming from one of the dressing rooms. We knocked on the door and found Victoria slouched over a bottle of wine, with streams of black mascara running down her face. She was crying her eyes out. She sobbed loudly, saying that Lorne (the show producer) had cut her out all her skits and she was going to quit show business.

Victoria got the call that her limo was ready, so she led us, and the wardrobe women, the hair stylist and the make up artist downstairs, where we all piled in the back of her stretch limo for the ride home. We shuttled through Manhattan dropping off the SNL crew members on their respective street corners. Once we were on I-95, she got on her car phone and called her boyfriend in Miami (this was pretty amazing to me, cause this 1992 BC… before cell phones). She cried all the way back to Westport, and in famous baby doll voice, told her Miami cop boyfriend that she hated show business and was going to give it all up, move to Miami, and marry him. She said she wanted to be just like the sweet railroad conductor and his adorable pregnant wife who were sitting across the seat from her.

And that’s just what she did. She quit show biz, moved to Miami, married the cop and had more children. I guess we inspired her.

For every famous person you’ve encountered, you’ve met quite a few more “ordinary” people. What is your most memorable encounter with a regular “run of the mill” train rider?

My most memorable “ordinary” passenger was probably the extremely grouchy woman who often rode my evening rush hour train home. This curmudgeon complained every time she saw me, and for some reason, she always seemed to sit in my car. She’d complain that the train was either too hot or too cold. The PA was too loud or she couldn’t understand my announcements. She groused about the the train being dirty or that it smelled like a urinal.

One particular night, she rattled off a laundry list of complaints as I stood patiently by waiting for her to finish. She went on and on till the surrounding passengers began rolling their eyes. Some commuters shook their heads and took pity on me. When she finally finished, I took a deep breath and asked, “Did you have a tough day at work today?” She suddenly burst out laughing, and I could see the tension leave her body. “As a matter of fact I did… it was a horrible day” she said with a big smile on her face. She loved me from that day on, and I never heard her complain again… well, almost never.

Metro-North nights (especially on the NH Line from your stories!!) sound like they can be pretty crazy… yet you seem to prefer the evening trains. I know a conductor’s schedule can be difficult with family – does the evening schedule help, or do you like the punishment from the crazy drunks?

A female conductor friend of mine once said that in order to be a conductor on a late night train, you have to have come from a dysfunctional family. Her theory is that we’re survivors and are the only ones who could put up with all the craziness we encounter. She may be onto something here.

As far as my schedule goes, I hate getting up early in the morning, and in the railroad world, in order to get home at a decent hour, you have to start work at in ungodly hour…like 4AM. No thanks. I’ve missed a lot of my daughters’ field hockey/lacrosse games, and parent/teacher conferences (fodder for their therapists sessions someday), but I do get a lot of yard work done during the day.

You’ve mentioned that you knew a conductor that had a complaint letter written about them because of chewing gum. I’ve heard some other complaint stories about a conductor that let a bug fly into the train, and that after collecting tickets would spend long periods of time in the bathroom (passenger didn’t realize it was the cab!!). Has anyone ever written a complaint about you, or have you heard any other crazy complaint letter stories?

In my 25 years as a conductor, I believe I’ve only have one complaint letter in my file…but it’s a doozy. I heard it was double spaced and eight pages long. It was sent to the the Railroad Superintendent, the President of Metro North, and the Director of the MTA. The prose was a group effort, written by a posse of obnoxious bar car patrons who thought Metro North rules didn’t pertain to them (i.e. smoking on the train). I heard they called me a “fascist”.

I recently heard that a woman on the upper Harlem wrote a letter of complaint, saying she counted 183 automated announcements on her very early morning M-7 train. I guess she shows up to work a little bleary-eyed. Not sure how the railroad responded.

Have you gotten the chance to ride any M8’s yet, and if so what do you think about them?

Yes, I’ve worked the M8’s, and I like them. They’re shiny, bright and new… what’s not to like? I just hope I still like them were they’re no longer shiny, bright and new.

Do people on the train ever recognize you based upon your blog? Are any of your passengers aware of it?

Once a passenger saw me walk by and he got very excited… almost star-struck. “Is that Bobbyderailed?” he asked my assistant conductor. I was flattered that he recognized me, so I walked to where he was sitting and thanked him for reading my blog. He showed me what he had just tweeted: “Wow! Bobby from ‘Derailed’ is the conductor on my train.” I think I stood a little taller that night.

On the flip side, I once overheard one of the female conductor sharing a funny story in the stationmaster’s office. It seems she had a male passenger on one of her morning trains and the gentleman had an explosive episode of diarrhea in one of the train bathrooms. He left the whole area a terrible mess, and at the last minute, he ran out of the lavatory with his pants still unbuckled and scurried off the train just as the doors closed. She said she didn’t know the guy’s name, but she was kind of surprised cause he was one of her regular passengers. “He sounds a little irregular to me,” I joked. I’m leaving out a lot of details, but her story was funny in a disgusting, over the top kind of way.

I took this story and embellished it a humorous blog post and did my best to portray the irregular passenger as weirdo…a real deviant of society. I must admit, my story was pretty funny and it was a favorite of my readers.
About a week later, the alleged deviant wrote a letter of apology to the female conductor. It turns out he’s one of my regular readers and he read, and recognized himself in my blog story. He’s also someone I happen to know and like (small world, huh?). To make matters worse, I learned he’s battling colon cancer and has problems controlling his bowels. As you can imagine, I felt horrible about how I portrayed him… still do.

Was there any particular reason you started blogging in the first place? Does your family ever read it/what do they think of it?

A few years back, my nephew’s journalist fiancee started writing a blog. They lived in North Carolina and I had never met her, but felt I did since I read about the daily minutiae of her life. I liked her blog so much that I started commenting on her posts on a regular basis. Her readers found many of my observations humorous and some petitioned me to start writing a blog of my own. I was working late night trains out of New Haven at the time, and I knew I had plenty of material to write about. That’s how “Derailed” was born.

My extended family loves my blog, since I often write about family lore. My nieces and nephews tell me they’ve learned a lot about our collective family history from my stories. They often tell me to cut back on railroad stories and write more about the family. I had to give my immediate family (particularly my daughters) veto power over of my stories, since I sometimes “over-share.”

Have you ever thought of joining twitter?

No thanks! Facebook consumes too much of my life already.