LIRR President Rob Free to step down Nov. 20, says 'the timing was right'

Rob Free, who began his career cleaning train stations and rose to become the head of the largest commuter railroad in North America, announced Monday that he is stepping down from his position as president of the LIRR effective November 20.

The Port Jefferson resident, who turns 57 on Tuesday, said he has long eyed this year as his last at the railroad, but wanted too stick around long enough "to make sure we got through" some key milestones at the railroad, including its first union strike in more than three decades earlier this year.

"I just felt the timing was right. It's been a hell of a run. I'm extremely proud of what we -- and I stress 'we,' the whole team here . . . have accomplished," Free said in a telephone interview shortly after announcing his departure to his staff Monday. "I really have nothing but the highest regard and admiration for everything that this place does."

The Metropolitan Transportation Authority, the LIRR's parent organization, announced it will "conduct a nationwide search" for Free’s successor.

Free joined the railroad in 1992 and climbed through the ranks until being named acting president of the LIRR in October 2023, after former interim president Catherine Rinaldi stepped down. In April of the following year, Free officially assumed the role of LIRR. He earned $355,031 last year, according to payroll records.

Free’s three decades of experience provided valuable insight in reshaping the priorities of the railroad, which had been reeling from the messy rollout of the new Grand Central Madison service plan in February 2023.

By rearranging schedules and launching a new initiative to improve service reliability at the railroad’s busy Jamaica junction, Free led the railroad in setting modern non-pandemic era records for on-time performance and ridership, and oversaw a 10% bump in customer satisfaction between spring 2024 and fall 2025 — before it dipped again this past spring following the introduction of unpopular new ticketing policies.

The former "station appearance maintainer" also prioritized keeping stations in shape, including by stepping up bathroom cleaning efforts and curb appeal for stations not in line for major renovations. And he implemented several efficiencies aimed at lowering the railroad’s costs, including by reducing overtime.

"I was ambitious, but I wasn't overly ambitious. I just tried to do the best job in the job I was in. And it just worked out," Free said. "I was very lucky. People saw something in me and gave me an opportunity, and I just tried to make the most of it."

In a statement, MTA Chairman and CEO Janno Lieber called Free's record "a model to everyone who wears the LIRR uniform.”

Under Free, Lieber said, "has delivered better service, for more riders than ever. He has positioned this agency to continue delivering fast, frequent, and reliable service for years to come."

Free encountered some major challenges during his time at the helm of the railroad, including disciplining three dozen LIRR workers ensnared in an employee ID card counterfeiting and distribution ring uncovered by a three-year investigation by the MTA inspector general. Free fired two of the workers, and issued suspensions, demotions and wage forfeitures for most of the rest of the implicated workers.

He also led the railroad through two historic systemwide shutdowns in 2026: in February, when a powerful blizzard dumped up to 30 inches of snow on the tracks, and in May when a contract impasse led 3,500 LIRR employees to walk off the job for three days.

Despite his trials, Free said he'll leave the LIRR with "nothing but fun memories." Free said his only post-retirement plans are to "sleep past 4 a.m." and spend more time with his family.

Free’s leadership at the LIRR has received high marks from colleagues and elected officials, including Gov. Kathy Hochul, who last month credited the LIRR for leading a "transit renaissance" in New York.

LIRR union leader Anthony Simon, who began his career cleaning stations alongside the departing railroad chief, said Free "brought something to the presidency of the Long Island Rail Road that can’t be manufactured — decades of real operational experience."

In looking for Free's successor, Simon said he hopes the MTA "remembers what Rob’s tenure proved: running the LIRR requires more than management experience — it requires a deep understanding of railroad operations, respect for the workforce, and the experience to know what it takes to keep Long Island moving safely and reliably every day.”

Lisa Daglian, executive director of the MTA Permanent Citizens Advisory Committee, which includes the LIRR Commuter Council, praised Free for providing a "steady hand and calm leadership" throughout his tenure, even when faced with "difficult storms, tough negotiations, system expansions, and the recovery from the COVID-19 pandemic."

By Alfonso A. Castillo

alfonso.castillo@newsday.com@alfonsoreports

Alfonso Castillo has been reporting for Newsday since 1999 and covering the transportation beat since 2008. He grew up in the Bronx and Queens and now lives in Valley Stream with his wife and two sons.