Formerly Director of Operations at MBTA in Boston, CEO of Bi-State Development Agency in St. Louis, and General Manager of SEPTA in Pennsylvania
Interview location: A pizzeria in Fort Myers, Florida
How we got there: On foot & by Lee Tran bus
In one word, he describes himself as “Confident."
My first impression of Jack Leary is that I want to hug him. Jack used to run transit operations in Boston at the MBTA, in St. Louis at the Bi-State Development Agency, and in Philadelphia at SEPTA. Today I’m standing at the bottom of the escalator in baggage claim at Fort Myers airport when he walks up. He is wearing his retirement well in a bright orange button-down shirt tucked into pleated khaki pants with a brown leather belt. His sleeves are rolled up and fastened to a button at his elbow. Kind blue eyes peer out of frameless glasses, and every piece of white hair is combed perfectly across his scalp.
I had landed a half-hour early, but when Jack Leary has your flight number, he is in the terminal when the plane touches ground. Pulling paper out of his pocket, he unfolds the Lee Tran bus schedule. “Our bus leaves in a couple minutes,” he says, checking his watch. “You still want to ride the bus, right? Because I have a cah.”
His Boston accent disorients me for a moment, but I quickly translate cah to car. “Yes,” I say. “Let’s take the bus.” As we wait on the bench, I apologize for not yet being fluent in transit-speak. “I think I’ve asked most of the really embarrassing questions,” I say. “On fixed route, paratransit, multimodal transportation ...”
“That reminds me of a story,” says Jack. “When I left St. Louis, at the end of our last board meeting, one of the board members came up to me and said, ‘Now that you’re retiring, can I finally ask—what the heck does a headway mean?’”
Jack laughs, and I want to join, but I also have no idea what a headway is. “Oh you don’t?” he says apologetically. “That’s okay!” A headway, he explains, is the time on a bus schedule between arrivals at a particular stop. “So if a bus runs every ten minutes, it’s a ten-minute headway.”
I should say there isn’t an ounce of pretention or judgment from Jack. With regard to knowledge, he is democratic and would rather be understood than sound smart. He acknowledges that there is a lot of jargon around transit. “This project is a good idea,” he says. “A lot of transit history never gets recorded. I put in 35 years on the public side and never regretted a minute. Every day, I could sit back and say I did something, [like,] ‘I moved 900,000 people home before a snow storm.’”
Our bus arrives, and Jack has exact change ready for both our fares. He instinctively takes inventory inside, checking off the normal list: bus is clean, signs are displayed, Americans with Disabilities Act [ADA] requirements are met. Without prompting, he turns to me. “I should probably tell you the story of how I got to St. Louis,” he says, which was to build a light rail that the public didn’t want. “Everybody was against it,” he says. “In seven years [from 1990 to 1997], I probably was on a hundred radio shows, answering the same questions. Who’s gonna pay for it? Who’s gonna ride it?”
Second photo shows Jack speaking about St. Louis's new light rail in 1993 and the third photo shows Jack and colleagues celebrating a successful first year with the light rail. (Photos used with permission from Bi-State Development archives.)
On the day the city launched the service, 1,400 cars showed up—to park in a lot that accommodated 200. For three days, Jack explains, they made parking lots out of neighboring lands, pouring gravel everywhere they could. Soon the light rail was carrying 14,000 people a day—double what they had predicted—and with more than twice that number for baseball games.
In 2013, Jack was invited to an event commemorating the light rail’s 20th anniversary. “I thought maybe only 50 percent of the organization would even remember my name,” he says. At the event, he continues, there was a special anniversary train car covered in historical decals with pictures of St. Louis and the light rail. “In the middle—this big decal—they have a picture of me driving the train,” he says, shaking his head in disbelief.
When he saw one of his old colleagues, she presented him with a jar of Tootsie Rolls, Jack’s preferred candy that he used to keep in his office and binge on in the late-afternoon hours. At the agency, “everyone knew I had an open-door policy,” says Jack. Anyone was welcome to visit and take a handful of Tootsie Rolls. “Then people started bringing me Tootsie Rolls,” he says. “So the jar was always full.” Jack was touched that, 20 years after leaving St. Louis, his former colleague had remembered the tradition.
At the ceremony, when the agency introduced Jack, he received a standing ovation. “It was such a tremendous feeling,” he says. “It put tears to your eyes.” The honor is still bringing tears to his eyes. “I tell you, Laura Lee,” says Jack. “It was one of the highlights of my transit career—that five minutes—and I never thought anybody would remember who I was.” Jack savors the memory for a minute in silence, then checks the next stop. “I’ll tell you how I got started in transit,” he says, again without my prompting. “’Cause I’m going all over the place.”
One afternoon in the mid-sixties, he says, during his sophomore year at Northeastern University in Boston, Jack noticed a poster advertising a train operator’s examination at the MTA. “You know the MTA?” asks Jack. I tell him that I don’t. “You don’t know Charlie and the MTA?” I say no again, and he is shocked. “Today it’s the MBTA, but then it was the MTA. You can’t write about the MTA or MBTA without knowing who Charlie is, okay?” He tells me about a song by the Kingston Trio, released in 1962, about a fictional passenger named Charlie who doesn’t know about a fare increase to ride the T, Boston’s subway system. Charlie gets on the train but is unable to pay the extra nickel to the conductor collecting fare, and Charlie winds up stuck on the train forever. “You have to hear the song,” says Jack.
Jack signed up for the Massachusetts Transportation Authority (MTA) operator exam, and a year later, in 1966, he started driving the T. “At this point in my life people are saying, ‘You want to be a driver? Why are you going to college?’” But he continued with his education, majoring in Business Administration, and drove the train outside class. At the MBTA, he liked the schedule and the money. For a few nights in 1967, when the rail was under construction, he worked overtime as a flagman. “I made 315 dollars that week,” says Jack proudly. “I carried that pay slip around for years. That was huge money in those days.”
Jack realizes late that we’re approaching our stop, so we scurry up to the front of the bus. I accidentally step too close to the driver. “Careful, ma’am,” the bus driver says sternly, clicking her nails against the steering wheel. “Gotta stay behind the yellow line.”
I snap Jack’s picture when we are off the bus, and the driver, who is taking a five-minute break, notices. “You know in all these years I’ve been driving, I don’t have one picture on the bus?” she says, coming down the stairs. I offer to take one, and she hands me her cell phone.
“He worked in transit for 35 years,” I say, nodding to Jack.
“Thirty-five years!” she exclaims. “I’ve got 17, and my husband retired after 30, but he can’t beat him—35 years! Oh my goodness.” She tells us she likes to drive. “It’s so smooth,” she says. “It feels like you’re floating on air.” She looks at Jack. “Did you ever get that? Did you drive buses?”
“Actually I drove a train,” he says.
“You drove a train?” she says.
“I drove a train in Boston,” says Jack, mentioning he knows Steve Myers, who runs Lee Tran Agency.
“You know Steve?” she says. “You should have told him you were taking the bus. You woulda gotten a free ride!”
“Oh, that’s okay,” says Jack. “I like paying my way.”
She asks me to borrow my notebook and writes down Jack Leary’s name as if she’s met a celebrity, promising to tell Steve. When she has trouble tearing out the paper, Jack says, “Let me help you.” He folds the paper and tears it cleanly. “See how organized he is?” she says, getting back on the bus. “Thank you very much.”
As we walk away, Jack says, “I always remember to pay the fare,” pronouncing fare like feh-ya. “When I was head of operations in Boston,” he continues, “Governor Dukakis used to ride the train all the time, and he would insist on buying a token. He was very supportive of public transportation.” As governor, Dukakis took the Green Line to work. “You can guess as Director of Operations, I made sure the Green Line worked flawlessly,” says Jack. “’Cause he would call—even his wife called a few times—and say, ‘Jack, you know the trash barrels haven’t been emptied at Park Street today?’ And I’d say, ‘I’ll get right on that and find out why.’”
Jack and I sit down on a quiet patio at Grimaldi’s Italian Restaurant and order a pepperoni pizza. April in Fort Myers is sunny and pleasant, with a breeze. “So you started out driving a train,” I say. “And you got promoted.”
“I think what served me really well was I would do anything they asked,” says Jack. To illustrate, he tells me about one Sunday in Boston, when he reported to work at 5 a.m. during a torrential downpour. He finished his first run and was parking his train when “all of a sudden lightning hit the yard, and the power went off,” says Jack. “Without the power, there’s no air compressors, and without the air, there are no brakes. So in a short amount of time, they’ll lose their air, they’ll lose their brakes, and they’ll start rolling.” It was the supervisor’s job to secure all the trains with chains, and at the time the supervisor was a man named Jackie Beck, who was working in the yard by himself while the train operators were waiting out the storm inside playing gin rummy. Jack offered to help and together, “we lock the whole yard down,” says Jack, even though “it’s not in my job description, and I’m in the union.”
Jack didn’t think much about helping Jackie Beck until six months later, when he was given an award at the stationmaster’s office for going above and beyond his duties. Soon after, when a position opened up in the Planning Department, Jack was promoted. The MTA was becoming the Massachusetts Bay Transportation Authority (MBTA)—expanding service from 14 cities and towns to 79. In the Planning Department, Jack did whatever was needed, plus a little more. Over the next two-and-a-half decades, he climbed his way up the ranks to become the Director of Operations.
Recently, he was speaking to a group of college students, and one student asked how, out of 6,000 operators, Jack was the one to make it to the top. “Ninety-nine percent of the people say it’s because of politics, that I know people,” Jack tells me. “But I didn’t meet Governor Dukakis until I was already Director of Operations. The truth is, I always did a little more than I needed to.”
When our pizza arrives, Jack begins telling me about Philadelphia, where he worked from 1997 until 2002. “Philadelphia was a mess,” he says. “That’s why they brought me in.” Southeastern Pennsylvania Transportation Authority (SEPTA) was incurring huge deficits, ridership was low, and the board had lost all confidence in the previous general management. “From their [the Board’s] perspective,” explains Jack, “their [the management’s] answer to everything was always, ‘We need more money.’”
In his previous job at St. Louis, Jack had built something new and could create the culture he wanted to support the light rail. In Philadelphia, he had to work with what was already in place. “Philadelphia was a real tough city,” he says, reminding me of the infamous Christmas football game when angry Eagles fans pelted Santa Claus with snowballs at halftime. To preach customer service in a city that laughed about hurting Santa required “a huge paradigm change,” says Jack. At SEPTA, Jack told employees that riders should be as comfortable at their stations as they would be in the lobby of the Marriott. “In our business, the people on the bus were called loads,” explains Jack. “I used to go so far—and get some chuckles from this—that the passengers on our buses and trains are guests, and they should be treated like guests, not like paying customers.” At rush hour in the busiest stations, he occasionally hired entertainment for his guests. “One of the most successful ones were the swing dancers,” he says, smiling. “They were just terrific dancers, and the music was fabulous.”
Jack Leary with John Nations, the current President and CEO of Bi-State Development, at the MetroLink’s Twentieth Anniversary in St. Louis in 2013. (Photo used with permission from Bi-State Development archives)
To make himself accessible to employees, he visited the garages and talked to mechanics and drivers directly. “I’d make it known that if anybody had anything they wanted to talk about, I was there.”
At the end of his three-year contract, he extended for another two. His creative marketing, high employee expectations, and strong communication skills paid off. Ridership increased. Budgets were balanced with operating surpluses. Infrastructure and technology improved. From SEPTA, he tried to retire but ended up founding a consulting firm instead. “To be honest, the private side isn’t the same level of satisfaction,” says Jack. “There you work for the money.”
After we’ve finished our pizza, Jack looks at his watch and checks the bus schedule. “We better start to walk,” he says, “We can’t miss the three o’clock.”
As we get up, I ask, “With all the changes you’ve seen, what is a change you thought you’d see but haven’t?”
He thinks for a moment. “I thought for a lot of years that in my day I would see public transit be a priority equal to other public policies,” he says. “But I look around the country and see every city so clogged with automobiles that the productivity of the country is inhibited.” He recalls one day, being stuck in traffic on his way to address the Chester County, Pennsylvania Chamber of Commerce. To travel 17 miles outside Philadelphia took him an hour and 20 minutes. In his speech to the Chamber, he told them about his trip, saying, “We’d all be British if it took Paul Revere this long to go from Charlestown.”
In St. Louis, he remembers trying to garner support on the light rail from Governor John Ashcroft. “I thought I did a pretty good job making a case,” says Jack as we walk to the bus stop. “He turns to me and says, ‘You know, Mr. Leary, if you stop running those trains tomorrow, every one of those people on that train is going to find a way to get to work, and it’s not going to cost the taxpayer a dime.’” Jack shakes his head. “I said, ‘Thank you for your time, Governor.’”
To make public transit the priority that his generation could not, Jack wishes more bright young people would consider a career in the field. “Attracting talent is a real issue in this industry,” he says. “Nobody graduates from MIT and says, ‘I just can’t wait to go work for a bus company.’”
Jack and his wife, Joan, on vacation in the Greek Islands in 2010. Photo used with permission by Jack Leary.
He is delighted, however, that in his own family, the transit legacy is being passed down to the next generation. “At first my son didn’t want anything to do with what his old man did,” says Jack. “Twenty-five years later, he’s got my job at the T, running all of operations and today he’s managing a big agency in Toronto.” Jack smiles. “I’m proud to say he’s better at it than I was.”
When we get on the bus back to the airport, I ask, “What’s the most important lesson you learned in management?”
“Hire good people,” he says, without hesitation. “And make the message very clear on what the goal is. If they know the end result, don’t worry about how they get there. Just let them do their job.”
People Who Move People is a web series profiling individuals who have made an impact in public transit. The series has been initiated and funded by RouteMatch Software, an Atlanta-based company who is passionate about transit and proud to record these stories.