Robert Hanlon

Orient resident Robert “Bob” Hanlon passed away on Oct. 21, 2021, at the age of 74, after a long battle with cancer. He was comfortable and at home, just as he wanted.

Bob was born on May 13, 1947, in Oceanside, N.Y., to Joe and Joan Hanlon. He was the oldest of seven brothers who grew up in Howard Beach, Richmond Hill, Long Beach and Glen Cove.

Bob was an inventor and an explorer, with a curiosity that stayed with him his entire life. He painted, sculpted and wrote poetry and essays throughout his life. As a teenager, he built his own sailboat and taught himself to sail. He was a talented stained-glass artist and a skilled woodworker, and never met a napkin that he didn’t find to be in need of a schematic.

Bob spent his high school years in Baltimore, studying to be a priest. It didn’t take. But his love of learning persisted. He got a B.S. in psychology from Long Island University, an M.S. in counseling from the College of Staten Island, and a J.D. from Brooklyn Law School. The New York Times doesn’t give out crossword degrees, but he’d want you to know that he could consistently finish Saturday puzzles. And that they’re actually a lot harder than Sundays’. 

He began his career as a grammar school teacher and then served as the assistant director of special education for the Board of Education of New York City, where he was a fierce advocate for students with special needs. After many years working for the Board of Ed, he pursued a lifelong goal and went to law school in his 40s. He graduated magna cum laude, served as a federal law clerk, and grew to love his work as an intellectual property lawyer. He was a tireless advocate for his clients, referred jokingly to the opposing side as “the bad guys” and spent his free time trolling eBay for infringing products. He took great pride in having once beaten Disney in an IP dispute, and especially enjoyed mentoring younger lawyers. 

After retiring, Bob found new ways to be “part of the solution,” with a focus on civil service and his beloved North Fork community. He loved and respected civic discourse, and was deeply devoted to the Oysterponds community. He spent many evening hours representing homeowners’ interests at Southold Town Board meetings. 

He served for four years as the president of the Orient Association, and successfully led the fight to prevent Thruway truck traffic from being rerouted to the Town of Southold. He also led efforts to prevent Plum Island development, got approval for advanced wastewater treatment systems, increased the transparency of town government, and preserved numerous historic buildings. 

He served as an Orient Fire District commissioner and ran for Southold Town Board in 2019. (Which was ironic, as he spent most of his life detesting politics — to the point that he refused to join either party for decades. But he was ultimately moved by the notion that he could help, as he always was.) 

Until just a few weeks ago, Bob served as president of the Oysterponds Historical Society. He led the board with his charming combination of a relentless focus, grace and kindness. He strived to find consensus and do what was right and best for the society and the community he loved so much. He deftly navigated OHS through challenging times, and left it better and stronger than he found it.

And unofficially, he spent many an early morning with good friends that he valued deeply at the Orient Country Store, solving problems great and small.

Which ties into Bob’s first and greatest love: family. Which for him extended to everyone he chose to make a permanent and beloved part of his life, whether they were related to him or not.

He grew up close to his brothers and his cousins, who he lived with for many years. In his early adult life, Bob and his first wife, Lorraine, raised their two sons in Brooklyn and Staten Island, and had many happy years there, crafting, traveling and learning together.

Bob married Jessica Frankel in 1999. They lived on the Upper West Side and in Southold, and ultimately found their “real home” in an 1869 Orient farmhouse. It belonged to the Young family for generations, and Bob spent countless hours upgrading it, while staying true to its classic farmhouse style. Southold’s Historic Preservation Commission awarded the house landmark status in early 2021.

Bob and Jessica greatly enjoyed traveling. They cycled across Europe, sailed in the BVIs and swam with sharks in the Galapagos. Warm days were spent biking, kayaking and sailing in and around Orient Harbor on their Pearson Ensign.

Bob was extremely close with a special group of friends that gathered in Maine every summer, where he went by “Bib,” and was well known as the composer and performer of many a clever song or poem written to honor friends’ special occasions, or just to make a new person feel welcome.

Bob is survived by his wife, Jessica Frankel; ex-wife, Lorraine Hanlon; sons, Jay Hanlon and Ryan Hanlon; daughter-in-law, Dara Liotta; three brothers, Roger Hanlon, David Dictor and Billy Dictor; and many aunts, uncles, cousins, nieces, nephews and dear friends. And by his two amazing grandchildren, Griffin and Maeve (who he had been teaching to be amateur stonemasons, gardeners, sailors and statespersons).

He was predeceased by three younger brothers, Ricky Hanlon, Rusty Hanlon and Randy Hanlon. 

Bob was incredibly proud of both of his sons, and he adored his grandchildren, who lovingly knew him as “Papa Bib.” He was an avid reader and an eager student. He was ever-positive, with a perpetually youthful attitude about life. He woke up happy every morning, often ready with a joke or a funny story. He loved to cook and to dance, tragically often at the same time. He was generous with his time and talents, and known as the person who would be there for friends, family and just about anyone who needed help. Or pro bono counsel. And occasionally bail. 

He was the type of man who did the right thing when no one was looking. He sang Christmas songs in Latin. Loudly. Whether he was in church or in his kitchen. And despite his cancer diagnosis, he forever remained a happy soul and considered himself a very lucky person, thankful for all of the people and experiences that life had already afforded him.

A celebration of Bob’s life is planned for Saturday, Oct. 30, at the Orient firehouse at 11 a.m. All are welcome to attend.

In lieu of flowers, memorial donations may be made to the Oysterponds Historical Society or Community Action Southold Town, both of which were near and dear to Bob’s heart.

This is a paid notice.