By Jaime Franchi
It’s the early 1990s in Queens, NY. Jamaica railway station, where ten branches converge into one location, is teeming with commuters, coming and going, switching trains to head into Manhattan or Brooklyn. If you aren’t paying close attention, you might miss three station cleaners with mops in hand, cleaning the floors, emptying the garbage, and washing the toilets.
Different circumstances brought them to the Long Island Rail Road, the busiest commuter railroad in North America. One was just there to work a summer job before heading off to college in the fall; another counted this as his first step toward a stable life, where he’d make a pension and someday be able to provide for a family. And you couldn’t miss the third, who was just a few years older, and was looking out for them—and everyone else he met.
If you stopped for a moment and took note of these three young men: Rob Free, Hector Garcia, and Anthony Simon, you would see a commonality about them: they were each committed to being the best station cleaner the railroad had ever seen.
Both Rob and Hector were serious and studious. If there wasn’t a mop in their hands, there would be a book. Hector was working his way through college—first at Nassau Community College, then Columbia University. Rob studied the manuals, always with his eyes on the next logical step in his career at the railroad. “Hector was very quiet,” Rob Free tells Road Warriors. “He studied. He really stayed to himself. He was very low key. Anthony is… he lets you know he’s there. He has a great personality.”
Anthony was a couple of years older. He and Rob immediately hit it off, which formed a foundation of respect they have held to this day. Protecting, fighting for, and serving others are the keys to who he was and the foundation on which he would build his career. Anthony Simon went on to become the General Chairperson for the SMART Transportation Division, which represents conductors, track workers, building and bridge workers, track supervisors, car repairmen, and car appearance personnel. He also serves as an Alternate Vice President for the SMART Transportation Division International Union. Rob, the kid with his nose in the training manuals, was recently appointed the new LIRR President. And Hector, the quiet one who was just here for a summer job, celebrated his 32-year anniversary at the railroad and now serves as Chief of Staff.
It’s safe to say nothing happens on the Long Island Rail Road that doesn’t have the fingerprints of one of those three former station cleaners, who each share vision, drive, and the pursuit of excellence.
Anthony Simon – The Labor Leader
Anthony Simon cuts an intimidating figure. His features are sharp; his suits are impeccable. You understand before ever hearing his voice that he is not to be messed with. This is important because what he represents is something he holds very dear. He is the voice and the negotiating muscle for the workers. And no one messes with them. Not on his watch. Anthony is unabashedly emotional. He is driven by his capacity to love, and he loves with his whole heart. His personal goal is to provide everyone with the best healthcare coverage possible, something he gleaned from watching his underinsured sister struggle with cancer that ultimately took her life.
“My push was fighting for the little people.”
“My push was fighting for the little people,” he says. “Throughout the years, people have come to me with a problem or needing support or my help—job-related or personal or family-related—because they know I will do everything in my power to help them. That’s the most satisfying part. That’s what I love about this job.”
“This is a unique group,” Anthony says. “This is the largest commuter railroad in the northeast. You have two people who started out as station cleaners, the heads – one on one side, one on the other.” A labor leader’s job requires him to push against the powers that be as hard as he can. It can be a tricky role that can create enemies as easily as it can rally support. “We go back. There’s no nonsense. I say all the time: you took the bad road. I took the good road. You went into management. I went to the union!” Anthony laughs. “The passion we both have is to make sure everyone can come to work and collect a paycheck so they can raise a family.”
Labor called Anthony early on. He started in 1990 working half nights covering the foreman’s position as a station cleaner in Jamaica until he advanced to assistant conductor. In 1995, he became a conductor and then in ’96, he became a union official, starting at the bottom of the barrel in the startup position. In 2001, Anthony became the secretary-treasurer of the union and in 2006, took the organization over as the chairman. He has served five terms—unopposed.
As chairman, Anthony has successfully negotiated contracts, avoided what looked to be a sure strike in 2014, and enabled a workforce to keep their jobs through the COVID pandemic that saw unemployment skyrocketing, leaving the commuter railroad commuterless and employees vulnerable. Anthony counts his accomplishments “from saving someone’s job to negotiating one of the best contracts we’ve seen, to maintaining our healthcare coverage to maintaining our pensions to navigating a lot of hateful stuff people direct at railroad employees,” he says. “Railroad employees are hardworking individuals. LIRR gets pointed out for everything and this is the best railroad in the country. It’s run impeccably as far as labor/management, even with the bumps in the road and the battles we face.”
Negotiating contracts requires frequent interactions with elected officials. Sometimes those interactions are friendly; sometimes they get heated. Pushing back against administrations who attempt to stifle what Anthony believes workers deserve is where this job can get dicey—and very political. It takes a strategic mind and a fierce resolve to fight for what’s right and to come out on the other side of negotiations with respect. “In 2014, we almost went on strike,” Anthony recalls. “I was making that call. I remember it like yesterday, that’s another proud moment. We didn’t strike. We came to a settlement that was negotiated and we moved on.”
It can be a daunting tightrope and one Anthony walks with aplomb. With former Governor Andrew Cuomo so intimately involved with the major MTA/LIRR projects and contracts, a new relationship had to be formed with his successor, Kathy Hochul. “My relationship now with the governor, we don’t have to always agree, but she’s always been supportive of us,” he says. “She’s come out and picked up the phone. After we settled the last contract, she was the first phone call I got to say congratulations. There are things that we agree to disagree on policy. Not everyone agrees on policy, but I have a contract until 2026. We maintained our pension and healthcare. Nobody can debate that.”
He is quick to give credit to his dedicated team. “Our accomplishments are as a team. We’ve done so much. Not me, nor management did it. It’s the team. They’re living it. They’re working the trains.” If you come at Anthony saying that workers are overly compensated in salary and overtime—something the railroad has been heavily criticized for—he will not hesitate to have their backs. “We have two sides who are able to sit down and come up with compromises that work, but it’s not about working for us, it’s about working for the commuters. A lot of them don’t believe that, where we make too much money, but we’re also out of our houses how many hours per day? I know they don’t want to hear that when they see the big salaries but go out on the track when it’s 100 degrees out, swinging a sledgehammer out there. The conductors work all hours and all shifts while sometimes being physically and verbally abused. They never give up. I will always have their backs and do whatever is necessary to protect them.”
It’s not an easy job. You must be able to take the brunt of worker complaints and handle public scrutiny. Every person who has this position does it their own way, each to their own strengths. Mike Canino was Anthony’s predecessor and acted as Anthony’s mentor before he took over as chairman, offering advice, but mostly giving Anthony the space he needed to do it his own way. Years after, he told Anthony, “You far exceeded what I ever thought was possible.”
“He retired and he says, ‘Here’s the ship. Run with it’,” Anthony remembers. When he considers who he looks up to in this Long Island universe, he’s quick to list some names. “I look at Rich Shaffer, Jay Jacobs and Tom Gary. They’ve been not only political mentors to me, but friends to me. Even during the worst of times, they were there.”
Anthony is wistful when thinking over his career. It’s taken a lot of grit, a lot of hours and a ton of resilience. “It’s the families that take on the hardship,” he says. The late nights, the long hours. He’s missed some critical moments with his loved ones to keep the train running. After the loss of his wife of 35 years to cancer, he is pensive about the time and energy he’s put into the job. If he has a regret, it’s about finding the right balance between work and family. He has zero doubt that he ever could have gotten this far without the dedication and support of his wife Ann and the love of his son Anthony Jr., whom Ann affectionately called “Doctor” due to his doctorate in physical therapy, and his daughter Nicole, a speech pathologist, both of whom Anthony credits his wife with for instilling in them her infinite capacity for compassion. During the writing of this article, Anthony welcomed his first grandchild, a baby girl named Ava Ann after her beloved grandmother.
“I’m a union guy. I’m a worker.”
“I’m not this guy who’s running for elected office. I’m a union guy. I’m a worker. I started in 1990 cleaning toilet bowls and I just wanted to keep pushing and I wanted to keep helping people,” he says. “And now I have that opportunity so I’m going to do it as long as I can.”
Rob Free – The President
Rob Free never set out to be President of the Long Island Rail Road. He was twenty-two years old and was just looking for something with stability. Getting onto the railroad promised a career path that would offer benefits, a retirement pension, and a methodical upward trajectory that would afford him constancy and security. “That was the most important thing to me,” he tells Road Warriors. “I never set out to say I want to work for the railroad. It just worked out that way and I’m thrilled that it did. I could have never imagined this journey taking the course that it did.”
The station cleaner’s position was his entryway into the organization and the jumping off point from which he would climb. Yet, he didn’t take the cleaning position for granted. He set out to complete each task he was assigned with excellence. “I remember cleaning the locker rooms over at Hillside – when I clean something I clean it!” he says. “I was taking out stainless steel cleaner and it was spotless. I was in the locker room and the guys were like ‘Where you been?’ and I was like, ‘Cleaning! This job is really hard,’ and they laughed at me.”
That’s the mark of who Free is as a worker. Dedicated, focused, and driven. Those traits led him to continuously climb the ladder from cleaner to block operator to chief train dispatcher and eventually to management, one foot steadily in front of the other. “I remember Rob,” says Hector Garcia of young Rob Free. “He was always studying. He did his job, and he always had his books and his notepad. I remember seeing him and thinking ‘This guy knows where he wants to go.’”
All he really knew was that he would try his best to achieve what came next. And he became fascinated by the inner workings of everything Long Island Rail Road and convinced that he could help make it better. “It naturally took its course,” he says. “There are people that help you along the way – that recognize something and gave me some opportunities and I think I capitalized on them and did a good job.”
Free’s mentors include two previous vice presidents of operations: Daniel Cleary and Raymond Kenny. Cleary was responsible for getting Rob on the railroad. Rob admired how he remained humble no matter how high he ranked in the hierarchy of the LIRR’s management team. Raymond Kenny inspired Rob with his patience and his ability to listen to people. “Both of those people—they cared for people, they loved this place,” Rob says. “Ray was more of a rail historian, and he loved that piece of it. Just his empathy for others and how he loved the LIRR and his compassion for people. We grew very close. Unfortunately, he passed away during COVID. Dan Cleary was like my father. There’s a picture of him in my office and I look at him and say, ‘I hope I lived up to the job that you expected.’”
As far as “living up to the job,” let’s take an assessment. He leads the team in how to deliver on projects while still delivering a high level of service. Multiple transformational, generational projects were delivered in just five years: Ronkonkoma double track, mainline third track, Elmont UBS station, and Grand Central Madison—just some of them—in the middle of a worldwide pandemic. For example, the completion of Third Track took unprecedented coordination. “When I say there were meetings, there were meetings every day on how to deliver that project in the middle of one of the busiest corridors in our operation. And, then to further complicate things, it took place in the middle of COVID.”
At the same time, east side access was taking place, so the team was able to deliver both of those projects in the middle of COVID – successfully and on time. During that time, they capitalized on the reduced service plan, performing essential repair work that set the railroad up for years to come. “We maximized because what we call Track Time – having the ability to work on the tracks is a premium when you are in service,” Rob explained. “It’s not a greenfield situation. It’s an active operation and that active train operation is the busiest commuter railroad in North America. So not only deliver on the projects, but we delivered on essential state of good repair work throughout the system. Something that was truly remarkable and really a testament to the workforce here.”
“What happens here every day is nothing short of a miracle.”
The mark of a true leader is to be first in line for criticism while being last in line for recognition. If we hold Rob Free to these standards, he excels. Every time a train is late, each construction project that upsets the public, every issue that inconveniences riders—he absorbs the complaints. Yet, he is undeterred. Even more impressive is that he retains his endless passion for the complexities of the system. “Long Island is a tough place,” he says. “This operation is like no other at least in this country. We provide service to five Western Terminals. There’s not a system that does that. Most systems go from point A to point B. One major terminal. We have multiple major terminals. We have Jamaica – 93 switches, 140 signals – ten branches converge on one location. We have 6 major junction points where other branches converge onto the main line. It’s extremely difficult – developing schedules and trying to figure out where your ridership is going and then determining all the smaller pieces: the equipment cycles, where they go, where they have to be, having the right size of equipment, then maintaining the tracks. What happens here every day is nothing short of a miracle. It’s that difficult this operation.”
Rob Free talks of the railway systems with a unique reverence. He is the person you want at the helm of the railroad, something he has dedicated his adult life to understanding and improving. “As much as things have changed here over the years, we are still a family. I always say the railroad is not a job. It’s a career. But it’s even more than that: it’s a way of life.”
“It’s a career. But it’s even more than that: it’s a way of life.”
This way of life takes a lot of support at home and that’s something Rob will never take for granted. When asked what brings him the greatest joy in his life, his answer is instantaneous. “I have an incredible wife who has been so supportive of my career,” he says. “An incredible mother. You talk about patience – she puts up with me first of all and then as far as my career, my schedule. It’s been crazy hours. It was probably close to 20 years of working 3-11 shifts, she was always there supporting me, and my children just give me the greatest joy. As I said I have two older ones and two younger ones. They truly are miracles. Hands down my family gives me the greatest joy.”
Hector Garcia – The Diplomat
When Hector Garcia breaks into a smile or gives a soft laugh, you can see him as both a child and as a mastermind. He is quiet. He is respectful. And he is sharp as a tack. But most importantly, he is patient, working diligently behind the scenes, executing every job with both excellence and vision, understanding not only what needs to be done in the immediate, but the organization and the surrounding structures and mechanism, and what will need to be done in the future.
Hector never planned to work at the Long Island Rail Road. A cerebral teenager, he was interested in studying Greek philosophy and political science. He thought he’d grow up to be a college professor or perhaps a politician. “Early on, I knew I wanted to become something,” he told Road Warriors. “I was always driven. I just didn’t know how to get there.”
It turns out, it was anything but a straight line. As the saying goes, we plan and God laughs. Hector knew he wanted to be paid to think someday. He enrolled in Saint John’s University as a political science major. A reservist for the Marines, he had completed boot camp after graduating high school and as he was getting ready to begin his second semester of college, Operation Desert Storm began. He was called into active duty. “I was in denial,” Hector says. “A week before I had to leave, I went to school the first day of my semester and I went to two classes knowing I had to leave for the war. After the second class, I was like, What am I doing? I’m not going to be in this class. I’m gonna go die.”
Garcia shipped out to California for training. He wanted to be an intelligence officer, but legislation was enacted before boot camp that required both parents to be US citizens to work in intelligence. Hector’s father was a US citizen and his mom was legal, but at that time was not yet a US citizen. Hector was given this news and a choice of options: a truck driver, cook, administration, or communications. He chose communications. “I thought it sounded cool.” Hector quickly learned that communications in a war zone does not mean writing press releases but carrying a radio with an antenna and batteries attached to the water platoon, the infantry that’s going to be out there. When you have the antenna, you are the enemy target. Everybody wants to kill you because they want to cut off communications. Luckily, after four months of active duty, the war ended two weeks before Hector was due to ship out to Iraq.
That summer, he took a job as a station cleaner at Jamaica Station, working with Anthony Simon and Rob Free. He thought he’d only be there for a month before school started again, but when he came home from his first day on the job, he found out that his father had been laid off from his airline job after twenty-five years. That changed everything. Hector felt compelled to keep working and initially, he believed that his college dreams were over. “I was in a funk for a few weeks,” he says. “And then I said screw this I’m going to do it. I transferred to Nassau Community College and then I started that September. Full time school while I was working full time.”
He kept up that schedule working nights so that he could go to school during the day. After two years, he graduated with his associate degree and transferred as a college junior to Columbia University, still working as a full-time station cleaner. After his first year at Columbia, he became a ticket clerk. It was a job in the daytime working a 6 am to 2 pm shift, which afforded him time to go to school in the afternoon and take evening classes. It took him three years to get his bachelor’s that way. “You take a typical ticket window when you’re on the island,” he explains. “You have a sleepy shift. From 6 am to 9 am is rush hour and then after that it’s dead. You can study.” After three years at Columbia, he graduated.
With an Ivy League degree in his hand, Hector contacted human resources at the railroad, looking for opportunities in management. He had no such luck: they suggested he study to be a conductor. He was told with overtime pay, he would be able to make a good living. That wasn’t the answer he was looking for. He was married now, with a child at home. “You get typecast when you’re a cleaner,” Hector says. “You’re outcast. People just see you that way. So, how can you get a chance to be seen as something else?”
Undeterred, Hector kept his eyes open for an opportunity and found it in a summer job with the marketing and promotions department, organizing sightseeing tours to Montauk and field trips with schoolchildren to Broadway shows. This position came with long hours away from home, but it got Hector exposure out on Long Island and a chance to work in a more corporate role in the Public Affairs department where he was eventually promoted to manager. “I realized as a young manager at that time, you could dress down on Friday,” he remembers. “I was 29 or 30 and the lesson learned was to always dress up. You dress to the level that you want to be. And I saw myself a certain way and I started getting sent to meetings. ‘Oh, there’s a big meeting at the Belmont Stakes and the executives couldn’t go, so we can send Hector.’ You go to these meetings with 50 people, 100 people, and you are the one MTA/railroad rep, and everyone always turns to you and puts the railroad on the spot. You always have to be ready to say something. It was good training.”
“I always saw myself as a diplomat.”
Then Hector saw an opportunity: In 2007, with new railroad president Helena Williams, there was an opening in the Government and Community Relations department. Although Hector had studied political science, he had never experienced the practical affairs of elected officials. “It’s funny,” he says. “I’ve always been fascinated by politics, but it was more about reading and following it, but I was never in it. When you talk about mentors, my mentorship was reading a lot of biographies. I always saw myself as a diplomat and I was fascinated by the role of the chief of staff. These behind-the-scenes people – they’re public but they’re kind of making things work, these are the people who fascinate me.”
By immersing himself in this department, getting to know and understand the questions and concerns of the community regarding railroad projects, and appreciating the hows and whys of the political system on Long Island at that time, Hector became a quick study. The way it had been done up until then was that people weren’t notified properly, so when railroad workers would show up to do the work, the public would react. “There would be phone calls from elected officials telling someone at the railroad, ‘Stop the cranes!’ And that costs money and time. We’re wasting time and effort, and it was happening a lot. So, my thing was always trying to be more proactive.”
When the Republican machine controlled Long Island politically, they had a lot of say on the railroad. There was a lot of tension between the LIRR, communities, and the elected officials, who had to answer to their constituencies. Hector needed to find ways to work together. “When the elected officials are surprised when they don’t know what you’re going to be doing and the mayors are complaining to them and the residents are complaining to them, then they have no choice but to attack you,” he says. His role became the intermediary between the community and the elected officials—kind of like the communications job he trained for in the military. Effective, but a target.
“You have to fully understand it before you can come up with a strategy.”
To communicate well, you need a deep understanding of the projects at hand. By this time, Hector was immersed in the transformational projects that the LIRR was undertaking. “To communicate about projects and do the community outreach, I want to see the plans, I want to go to the site, I want to know how you’re going to build this – is there a synagogue there? Is there a church? A school?” he says. “You have to fully understand it before you can come up with a strategy. Sometimes I would go to the project manager and say, Why don’t you change this or do it this way?” His input, his exposure to the public, his reputation, and his network put him in a prime position to help tackle the nearly infinite complexities that came with the Third Track project.
Thirty years into this summer job, it’s safe to say Hector has taken on work that needs serious brainpower and political acumen. As the newly appointed Chief of Staff, his role as a behind-the-scenes diplomat now plays out, alongside the kids he started out with: Rob and Anthony. Without the dedication and leadership of these three men, the Long Island Rail Road might never have stayed on track.