Being a train conductor seems like a simple, boring job: collecting tickets, opening and closing doors, reminding people to keep their feet off the seats. Yawn.

But there’s a lighter side to the job, as I wrote a few years ago, based on former conductor Michael Shaw’s great book, “My Rail Life,” after he retired from a 36-year career on the New Haven line. He clearly loved his job. And he swears these stories are true.

He once told passengers on a standing-room only train: “OK, folks. We are half way to Grand Central. It’s time for everyone who’s been seated to get up and give their seats to folks who’ve been standing.”

Asked by a passenger boarding at Grand Central, “What times does this train arrive in Stamford?” he answered candidly, “Usually about 20 minutes after the schedule says.”

On another train he announced: “Folks, I have good news and bad news. The good news is that Metro-North fixed the air conditioning you complained about not having all summer long. The bad news it’s now winter.”

Honest to a fault, he turned in everything left by passengers on his train to the Metro-North Lost and Found … even an envelope containing $400 in cash. (The lost money wasn’t claimed so he got it back.) On several occasions, he’d find a lost briefcase or cell-phone and personally return it to the owner’s home the same day.

He also loved razzing his fellow railroad workers, once announcing, “If you have any railroad questions or would like to take your picture with a real railroad engineer, come to the front of the train and say hello to Jerry, who loves chatting with people.” The engineer’s name was not Jerry and the real man at the controls really didn’t like people.

Approaching Bridgeport, Shaw announced the connection for the Waterbury train, adding “Be sure to ask your Waterbury conductor for one of the free 100 Years Commemorative pins.” There were no such pins.

On Friday late night trains, Shaw would bet with his fellow conductors watching drunk passengers boarding at Grand Central, guessing who would be first to throw up. Shaw immediately chose a 95-pound blonde he saw staggering to the nearest car with her equally inebriated boyfriend. Even before leaving the station his co-worker came and gave him his winnings.

Shaw always went out of his way to keep passengers informed about delays. In the horrendous winter of 2014 when the railroad almost ground to a halt, he printed a one-page apology for the previous day’s delays and did his own seat-drop of 500 copies before the train left New Haven. His regular passengers were so grateful for his candor, they gave him a standing ovation as he entered each car to collect tickets. His railroad bosses were not amused.

Approaching an obviously “senior” citizen to collect his fare, the old timer asked if Shaw needed his ID to prove his age. Saying that wouldn’t be necessary, the old timer asked, “Are you saying I look too old?” “No,” said Shaw. “You look honest.”

On another occasion he approached an elderly, grey-haired woman, who wanted to buy a senior-discount ticket. “Are you over 65?,” he asked in a teasing voice. “Actually, I’m 82” she said. “Well, you look marvelous!,” said Shaw, asking “What’s your secret?” Without a smile or batting an eyelash, she said “Rough sex.”

If you need a good chuckle, you’ll love this book.

Editor’s Notes: i) Jim Cameron is the founder of the Commuter Action Group and advocates for Connecticut rail riders. He writes a weekly column called ‘Talking Transportation,’ which is published by a number of publications in the state.
ii) ”Talking Transportation” won first place in the general column/commentary category in the 2024 Connecticut Society of Professional Journalists Excellence in Journalism Contest.