Ray Kenny fell in love with the Long Island Rail Road riding a 1920s-era electrical train from his hometown of Cedarhurst to Molloy High School, not far from the LIRR's Jamaica Station, nearly a half-century ago.
"We had jointed rail, so you'd hear the clacking," said Kenny, 62, sitting in an office inside the LIRR's headquarters, with a window looking down onto the Jamaica platforms. "I used to stand there and just watch the movement of the trains. And I became interested in how that was done."
Kenny would go on to learn how, exactly, that was done, and so much more in a 44-year career in which he did everything from selling tickets to leading the largest commuter railroad in the continent. And on Friday, he retired.
"I really have a respect for and a sense for what everybody does, because I've worked at different levels . . . They know, at some point, I walked in their shoes," said Kenny, who served most recently as the LIRR's senior vice president of transportation and facilities planning. "I never in a million years thought I'd make it that far."
Kenny, who now lives in Lindenhurst, first began working for the LIRR as a summer ticket clerk in the early 1970s, while pursuing a bachelor's degree in business administration from John Jay College. After graduating, he was hired full time on the management side of the LIRR as a junior industrial engineer.
Over the next four decades, Kenny moved from job to job, along the way learning another side of the railroad's expansive operation. As a training department manager, he helped put together instructional manuals for employees. As a manager in the service planning department, Kenny led an effort to untangle the LIRR's complicated evening rush hour.
When Kenny was promoted to chief transportation officer in the early 2000s, the MTA was planning in earnest for its most ambitious project in a century — East Side Access. The plan entailed bringing the LIRR to Grand Central Terminal via newly dug tunnels from Queens to Manhattan.
"It was at the point where it became viable, in terms of the support and the money," Kenny said. "The question was: How do we do this?"
Kenny then faced what would be one of the biggest challenges of his career when he was appointed acting president of the LIRR in 2006, replacing retiring president James Dermody. Kenny held the post for 10 months, along the way leading the LIRR's efforts to address concerns raised by a Newsday investigation about the dangers of wide gaps between trains and station platforms.
"I was not stressed, because I had a lot of help. Everybody was pulling the same weight," Kenny said about his time as acting president. "I really did enjoy the job. I tried to bring the place together."
Kenny applied for the permanent job as railroad president, but was beat out by current president Helena Williams, who was assigned the position in 2007. Kenny considered retiring then, but Williams helped persuade him to stay on as her No. 2, in the position of senior vice president of operations.
"Ray Kenny knows every switch, signal and interlocking on the Long Island Rail Road, and he could virtually recall them at will. I'll say, 'Ray, what about over here?' And he'll immediately be able to tell me what's there, what it looks like and what trains can do at a particular location," said Williams, who credits Kenny as a mentor during her earliest days as president. "He's really a true railroader."
Kenny, who already has two master's degrees in government and politics and in psychology, plans to spend his time away from the LIRR completing his third master's, in emergency management. He doesn't rule out a possible return to the LIRR in a consulting capacity.
"I'm a person who doesn't really believe in retirement," Kenny said. "I still have it in me to stay in the industry."
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