Title:John T. Hayden (1948-2024)

John Hayden was a man of many contradictions. He was a warm and kind friend who maintained relationships from childhood on, but he was intensely private, even with his closest friends. He was generous with others but, except for travel, didn’t spend money on himself, driving the same car for decades. He loved performing in theater as a hobby but never let nearby friends know that he was in a show. A successful businessman who enjoyed hiking and could buy the latest gear, he wore boots held together with duct tape.

Until his death in 2024 of leukemia, Hayden owned and managed a sprawling portfolio of more than 40 properties across nine states, ran the business by himself and did all the management work by hand, never using basic software.

But for all his contradictions, he was deeply loved by family members, friends and everyone who came into his orbit. “John was very private and didn’t share a lot of personal details, but we all loved him,” says Boston College friend Matthew McEntee.

A Catholic upbringing in D.C.

Hayden was born in 1948 in Washington, D.C. His paternal ancestors had migrated to D.C. from Southern Maryland a half-century earlier. “The family was very proud to be a D.C. family,” says Hayden’s cousin Zoe Ann Vest, with whom he shared a Hayden grandfather.

The Hayden men followed a Southern Maryland tradition and used their middle names as first names, Vest explains. Hayden’s middle name was Terrill, “so he was Terry, always Terry, to everyone—including outside the family.” If you knew John Hayden before college, you knew him as Terry Hayden.

Hayden and his brother grew up in the family home on Tunlaw Road in Glover Park, then and now a leafy, quiet D.C. neighborhood. The house stands today relatively unchanged; until his death, Hayden stayed there when he made regular trips to D.C. from his home in Berkeley, California.

The family were devout Catholics, and Hayden had a Catholic upbringing—a tradition that he left behind as an adult. His parents would invite priests to their home for dinner, including Jesuit priests from Georgetown University, several blocks from the Hayden house. Pride of place in their home were the religious statues and images Hayden purchased at the Vatican when his class at St. John’s College High School made a pilgrimage to Rome for a papal visit.

At St. John’s College High School, then a Catholic boys’ military school, Hayden met Jack Caspar, who would become his oldest and lifelong friend. “We were in the same homeroom, so we met on the first day of school. We were about age 14,” Caspar says. “We had many classes together and always got along. He was easy to talk with even though he was selective about what he shared.”

After graduating high school in 1965, both young men enrolled at the Catholic University of America, also in D.C. Caspar graduated, but Hayden left early. “Terry was plenty smart, and he got good grades in classes that he liked,” says Caspar. “But if he didn’t enjoy a class, he took a long car drive instead.”

After a short stint at Wheeling University in West Virginia, Hayden was accepted at his dream school, Boston College.

Friendships forged in college

Arriving at Boston College in 1968, Hayden soon met junior Matthew McEntee. McEntee and Hayden were friends for the rest of Hayden’s life. (For his new start, Hayden dropped “Terry” and used his first name, “John.”)

“John was a great student; he’d read all the material for class—both the required and the recommended readings,” McEntee says. “He was very disciplined.”

“John had a brilliant, analytical mind,” adds Terry McEntee, Matthew’s wife. “You couldn’t beat John on facts or analysis.”

Hayden had caught the theater bug in high school and performed in school plays and musicals. He quickly was on the boards at Boston College. “He had a great singing voice and a real stage presence,” McEntee recalls.

After graduating from B.C. Hayden attended law school at Washington University in St. Louis for a year. He quickly realized he wanted to be on the West Coast, and enrolled at UCLA Law, where he made law review. He was an early hire in the San Francisco office of what is now Littler Mendelson, PC, and practiced labor and employment law. Most importantly, the Bay Area became his home.

A new career takes root

Hayden’s passion eventually became real estate rather than the law. He bought one property, then another. Before long, Hayden was making more money from his properties than at work, so he quit the law firm even though he had made partner. “John was determined to retire at 40 and was disappointed that he had to work until 45,” says McEntee. (Caspar adds that in high school, Hayden had said “he’d be a millionaire by age 30. It took until a little later, but he did it.”)

Hayden’s real estate portfolio would have been daunting for even a professional property management company. Eventually it grew to 42 properties with nearly 1,000 units—houses, small apartment buildings and huge complexes of hundreds of apartments—in locations ranging from Hawaii to the Mid-Atlantic to Washington, D.C. Together, they made him a very wealthy man. His frugality never betrayed his wealth, however. He drove old cars, he didn’t eat at fancy restaurants, and his clothing style was kindly described as “threadbare” by friends.

Hayden’s approach to running his business was decidedly old-fashioned, says Joe Gillach, a close Bay Area friend. “He was a paper and pencil guy,” Gillach says. Gillach paints a picture of Hayden’s business operations, which he managed solo. Hayden’s “office” was a card table and a folding chair in the living room of his small one-bedroom apartment in Berkeley, devoid of any other furniture or even art. All the records were on paper, and his filing system consisted of piles of paper and scraps of notes everywhere. No electronic records, no voicemail, no email. And each property folder was labelled with a code that only Hayden understood, rather than a street address.

“By the end of his life, John had a cell phone, but I am not certain that he really knew how to use it,” Gillach says. Another Bay Area friend, Ken Robin, adds that tech was the only area where Hayden wasn’t confident. “He didn’t even have a FastTrack transponder in the car to pay tolls; he just would use the toll-taker line,” until their elimination forced him to reluctantly adopt an electronic device.

A saint among hikers

Hayden was drawn to and stayed in California partly because of the vast amount of outdoor space and the proximity of state and national parks. He was enthusiastic about running, biking and tennis, but once he began hiking, he was hooked. He spent almost every weekend on a trail, sometimes alone, but he regularly hiked as part of the San Francisco Hiking Club. Ken Robin met Hayden through the hiking club, and they became close friends. “John was always there. He had an impact.”

His singular presence in the hiking club earned him the nickname “St. John.” “He always brought water to share and big chocolate bars for energy in his backpack,” Robin recalls. “I once picked up his backpack at the start of a hike, and it felt like an anvil was in there. Although he was a very accomplished hiker, he was always bringing up the rear of a hike to be with and help the slower hikers,” Robin says.

Again proving Hayden’s lack of interest in spending money on himself: “His hiking boots were held together with duct tape,” Robin adds.

Playing many parts

Hayden’s love of theater, especially American musical theater, was sparked in high school, deepened at Boston College and never ended. He had a commanding knowledge of musical theater; he knew shows, songs and lyrics by heart; and he had a large collection of records.

Hayden regularly performed on stage in the Bay Area, though you’d be lucky to know it. Even close friend Ken Robin says, “I’d find out later that he’d been in a production.”

He most often performed at Woodminster Theater in Oakland, California, near his Berkeley home, appearing as “Chris Terrill” (resurrecting his middle name). When he started performing, he was still practicing law and was concerned that the firm wouldn’t approve, thus the stage name.
“Chris was a regular; he performed a few times a year for about 15 years,” says Jody Jaron, choreographer and manager at Woodminster Theater. “He did all different kinds of parts.” Indeed, a list of his roles showcases many gems of American musical theater: Guys and Dolls, Damn Yankees, Once Upon a Mattress, Into the Woods, Man of La Mancha and more.

“Chris had a rich, beautiful voice. On top of that, he knew how to create a character,” Jaron says. And he was modest. “He just wanted to be in the cast, he didn’t need to be the star,” Jaron adds. “People looked forward to working with him. He was a team player who encouraged others. Not all performers are like that,” Jaron adds.

His cover as Chris Terrill was blown when someone found out that Hayden was performing, went to Woodminster Theater to buy a ticket and mentioned that they were there to see a friend, John Hayden, perform. “We said, ‘We don’t have a John Hayden in the cast. We never have,’” Jaron recalls. The ticket buyer pointed to the cast photo of “Chris” and said, “‘That’s John Hayden,’” Jaron says. “After that we called him Double Agent Terrill.”

“John and I both loved musical theater and talking about it was part of how we became friends,” Gillach says. “But I didn’t know that he performed at Woodminster until after he died.”

His longtime friend Terry McIntee adds, “Somehow, I managed to see him perform in Oklahoma. I don’t think John was happy about it.”

Meaningful connections

Hayden believed in keeping family and friends close, having lost his only brother, who died in middle age. From the West Coast, he telephoned relatives to be sure that they didn’t lose touch and always sent boxes of See’s Candy, a delicious Bay Area tradition, to friends and his few surviving relatives on every holiday. And although he had not practiced law for decades, he remembered a beloved former legal secretary with regular boxes of candy.

He developed an interest in family history, which brought him close to his Hayden cousin, Zoe Ann Vest. “I didn’t know Terry very well or see him very much when I was a child,” she says. But their shared interests opened a door. “We’d talk and share information. That’s how we came to really know each other,” she says. “He meant a lot to me, and I think it meant a lot to him to be connected to me.”

Venturing everywhere possible

Hayden loved to travel.

“The only thing he spent money on for himself was travel,” Caspar says. “John loved to drive, loved road trips, even by himself. What he liked best was to explore new places. He wanted to see everything there was to see.”

Hayden often combined his passion for hiking and international travel by venturing to remote places with friends from the San Franciso hiking group. And while his companions took photos, the technology-adverse Hayden would collect postcards, which he would later show to friends rather than photos.

Fueling his passion for travel was the arrival of National Geographic magazine, which he eagerly awaited each month. The magazine also fed his love of the natural world, from plants and forests, to geography, to geology and space. “I bet that John had every National Geographic ever published,” says Robin, as evidenced by an entire hallway in Hayden’s apartment lined with hundreds of dogeared magazines.

Tending an outdoor showcase

Just like travel and hiking, if you knew Hayden, you knew that he loved plants and gardening. But it’s hard to garden in an urban apartment in Berkeley. “That’s why Terry bought the second house—to have room to garden,” Vest says.

Ever the property hunter, Hayden bought a house about 15 miles from Berkeley with a one-acre gently sloping hillside. He never really furnished the house or lived there, but he built an extensive garden over two decades. Friends and family say that the garden was his favorite place.
Hayden hosted an annual pool party for the San Francisco Hiking Club. “He’d spend weeks getting the yard and garden ready for the party,” Robin says. “It was really a showcase.” Hayden hosted the last pool party in August 2024, shortly before his death in October. The hiking club gathered around the pool one last time to remember Hayden, and had the opportunity dig up and take home a plant from the garden to remember him.

An explorer to the very end

In 2022, Hayden was diagnosed with a rare blood cancer, Chronic Myelomonocytic Leukemia (CMML). He was in a clinical trial at UCSF for 14 months post-diagnosis before his doctors stopped treatments.

“He kept his sunny disposition. He never, ever complained,” Robin says. He also never told even the people closest to him how ill he was.

“People absolutely adored John. But he’s particularly hard to capture. I always had a feeling that I was only getting part of John,” Robin says. “Even people who knew him longer than I did learned a lot about him after his death.”

Only a month before he died, Hayden made a last trip to D.C. He and Jack Caspar took a few days to enjoy the nearby beaches in Delaware and Maryland. Afterward, Hayden drove his Mercury Marquis—so old that everyone begged him to get rid of it—from D.C. back to Berkeley. “He didn’t look good, and I tried to dissuade him from driving himself, but he drove back to Berkeley, stopping along the way to see things he wanted to see,” Caspar says. “He was exploring up to the very end.”

Hayden died in October 2024 and was buried in the family plot in Maryland alongside his brother, parents and generations of Haydens. His ashes were placed in an REI backpack, along with a compass and hiking maps to guide him on his journey.

Hayden designated three Catholic educational institutions—St. John’s College High School, Boston College and Georgetown University—as beneficiaries of his estate, a testament to the impact of his faith-based education and upbringing. A man who went by many names and pursued many interests, Hayden found constancy throughout life as a friend, adventurer and lover of the outdoors.