The Oracle of Oklawaha

By Randy Noles

The son of Winter Park’s most renowned architect, Gamble Rogers spurned the family business and set out to live a troubadour’s life. In doing so, he left a musical legacy as enduring as his father’s elegant homes.


His grandfather, father and first cousin were all prominent architects. Yet, despite his own architectural gifts, he chose a life as a guitar-toting troubadour, celebrating rural Florida with whimsical stories, evocative songs and skillful fingerpicking.

He toured North America for nearly 30 years, presenting a category-defying one-man show that took him from raucous bars to intimate listening rooms to the stage at Carnegie Hall.

He drove Florida’s back roads in a fastback Mustang with an unknown songster named Jimmy Buffett, who years later would dedicate an album to him.

He died in the Florida surf in 1991, trying to save the life of a Canadian tourist he’d never met. It was an act of bravery that his friends say was entirely in keeping with his character.

In his memory, friends and colleagues launched a successful, long-running folk festival, a memorial foundation and a website where fans from all walks of life continue to express their admiration for his life and work and their sorrow for his death.

The beach where he drowned and a St. Augustine middle school have been named for him. His manager, at his own expense, has ensured that his albums have remained in print.

Now, 22 years later, friends still display a mixture of affection, reverence and unresolved grief that causes them to tell the story of his drowning death as if the outcome somehow still hung in the balance; as if this time, it didn’t have to end the same way.

Should all this seem too mythic for any real human—especially one you’ve never heard of—then welcome to the world of Gamble Rogers.


Songwriter and performer Mike Cross describes Rogers as “a man who had command of the stage and could create a world that people could escape into for the time he was performing.”

Delivered with clear diction and a reedy vocal timbre, Rogers’ singing style never strayed far from the cultured Southern dialect of his speaking voice. His vocals were punctuated by energetic thumb-picked bass lines and buoyed by arpeggio guitar flourishes.

No less a storyteller when he was singing than when he was speaking, he favored songs with narratives, despite the challenges of drawing audiences into that genre.

Throughout his career, he often challenged his own artistic range, performing songs with story lines that were funny, poignant, heroic or dissolute.

Some were traditional, and some he wrote, calling them “Southern Gothic art songs.” Others were written by friends, just for him to perform.

For his stories, he painstakingly composed serpentine, alliterative, mock-scholarly sentences and then practiced them before a mirror until he could deliver them in long, energetic bursts.

Audiences would start chuckling at the first laugh line, not knowing that seven more would come before the sentence ended. (As for the storytelling class he sometimes taught, Rogers named it “Liar’s Workshop.”)

While Rogers fulfilled multiple roles—author, storyteller, songwriter, singer and guitarist—audiences felt they were experiencing the man directly and naturally, as if they’d just caught him holding forth from the loading dock at Arrandale’s Purina Store in Oklawaha County, the fictional Florida backwater in which many of his tall tales were set.

“Gamble came about as close as anybody could to being onstage what he was in real life,” says Cross. “He didn’t have to hide anything—there was so much good in him that he could just strip naked.”

A lanky, angular figure standing more than 6 feet tall, Rogers dressed unpretentiously for the stage, but with dignified touches such as wool blazers and conservative brown Florsheim Imperial cap-toe shoes. His work ethic was prodigious and his presentation at times frenetic, like a televangelist on speed.

A tireless performer, he wanted to give his audiences more than their money’s worth, yet still be true to the performer’s dictum: always leave them wanting more.

“The contracts [for Rogers’ performances] would just blow your mind,” says Cross. “It would be a five-night run, and the contract would say, ‘Tuesday through Thursday: three 90-minute sets; Friday and Saturday: three 120-minute sets.’ Three sets! Six hours!”


If the bred-in-the-bone gallantry of a Southern gentleman can be a tragic flaw, it would be just about the only one anyone ever found in Gamble Rogers. His manners were old-fashioned and courtly, and he was patient and generous with his audience.

When fans met him, he treated them as if they were the stars and he had all the time in the world to visit with them. Emotion-filled messages posted at describe such encounters, remembered vividly despite the passage of years or decades.

Friends and fellow artists describe Rogers as someone who had achieved a near-seamless blend of life and art, with well-measured ingredients: humility, wry humor, obsessive technical excellence, literary acumen and an affectionate, offhand conversational style.

“When Gamble showed up at a party,” says singer Bob Patterson, “people would greet him or try to get his attention. He’d acknowledge them, but he’d go around and say hello to the kids and dogs first.”

His sense of obligation to his fellow man was extreme. Rogers’ manager and agent, Charles Steadham, describes a breakfast meeting they had one morning in Micanopy, after his client had just come off the road.

Sleep-deprived and physically wrung out, Rogers wanted to deal quickly with the business matters of the morning and cover the few remaining miles to his home in Anastasia Island, near St. Augustine.

As they left, a man approached Rogers in the parking lot and asked to speak with him privately. Rogers agreed. Shortly thereafter, the man went to his car and drove out of the parking lot—with Rogers following in his Mustang.

The wife of the man at the restaurant was an avid fan and was near death from cancer. Rogers followed him home and performed a lengthy bedside concert for an audience of two. Postscript: At Rogers’ memorial service, Steadham recalled that story as an example of his friend’s altruistic nature. After the service a woman approached him and said, “The woman in that story was my mother.”

Rogers also championed other artists. St. Petersburg-based folk-singer Pete Gallagher recalls a controversy that erupted 30 years ago over the inclusion of a blues artist at the Florida Folk Festival, held annually at White Springs.

At the time, Gallagher was managing renowned African-American singer Mary McClain, a half-sister of Bessie Smith, who was usually billed as Diamond Teeth Mary. McClain performed a traditional blues set at the event, which angered traditionalists who later gathered for a wrap-up meeting.

“Everybody who was still around, artists and organizers, would come to this free breakfast and gripe,” recalls Gallagher. “They were griping about Diamond Teeth Mary being allowed to perform. Then Gamble stood up and said, ‘Would you deny your brother a seat at the table?’ There was silence, and all the griping stopped.”


“Oklawaha County is principally known for its outsized number of rural alchemists. It’s not what you’re thinking. We have an inordinate number of folks who spend the bulk of their waking hours puzzling out novel ways to bleach their used coffee grounds, so they can sell them to the tourists on the Interstate for grits—which goes a long way toward explaining why so many Northerners don’t care a hoot for Southern cooking.”

                                                      —Gamble Rogers


Born to energetic and sophisticated parents, James Gamble Rogers IV grew up in the crucible of a loving family of Renaissance-style high achievers.

His father, James Gamble Rogers II, was an architect and designer as well as a world-class swimmer and skilled musician. (A 1917 Vega banjo with a single-digit serial number, from the senior Rogers’ Dartmouth College days, is still in the family.)

Rogers’ father had attended Dartmouth on a swimming scholarship and qualified for the 1924 “Chariots of Fire” Olympics. He worked in a Daytona Beach architecture practice started by his father, John Arthur Rogers, before establishing his own firm in Winter Park, where his first son was born in 1937.

Over the course of a legendary, 60-year career, the senior Rogers designed many of Winter Park’s most elegant homes and helped define the look of the Rollins College campus.

His uncle (and Gamble’s first cousin), also named James Gamble Rogers, was equally accomplished, designing iconic buildings for Yale, Columbia and Northwestern universities. (For those attempting to follow the genealogy, the moniker James Gamble Rogers III, which would otherwise have been the folk-singer’s patrician-sounding designation, had already been taken by a grandson of this James Gamble Rogers.)

Rogers’ early life was marked by his social and intellectual gifts, his evident creativity, his precociously high personal standards—and a life-altering medical setback.

Younger brother Jack, who carried on the family tradition by becoming an architect, remembers Gamble attempting a high jump and missing the sawdust pit, jarring his spine on hard ground. The accident aggravated a serious but previously undiagnosed case of spinal arthritis.

For therapy, Rogers had to lie on a large stainless-steel reflector, under a heat lamp, for three hours a day. He passed the time by becoming an avid reader, which Jack believes helped galvanize his brother’s emerging love of language.

After graduating from Winter Park High School in 1955, Rogers enrolled at the University of Virginia. While there, he met several times with Nobel laureate William Faulkner, who kept office hours as writer-in-residence.

Rogers then decided to skip final exams and left Charlottesville to take guitar lessons from noted jazz guitarist Charlie Byrd in Washington, D.C. Jack notes, with the family’s gift for gracious understatement, that this resulted in his brother being “excused from the University of Virginia, for at least a year.”

Back in Winter Park, Rogers enrolled at Rollins College, where he befriended Professor Edwin Granberry, author, essayist and trusted biographer of Gone With the Wind author Margaret Mitchell. Granberry wrote a glowing recommendation that helped his young protégé get into Stetson University in Deland.

Rogers spent a year at Stetson before putting aside formal higher education for good. He had drifted through four years at three different colleges, majoring in architecture, English and philosophy. Yet he had no degree to show for his effort.

Again he returned to Winter Park and went to work in his father’s architecture firm, where he spent the better part of four years. It was more than a sense of obligation; he had a legitimate, perhaps genetic, aptitude for building design. But architecture didn’t stir the passions inside him that music did.

So Rogers began moonlighting as a folk-singer. It was about 1960 that he snared his first paid musical engagement, singing at a long-forgotten club called the El Caribe, which was located in a nondescript storefront on Park Avenue North.

About 20 people were in the audience on his first night. And even though his inherent shyness made it difficult for him to get onstage and perform, the experience convinced him that he had found his true calling.

Eager to pursue a career as a performer, Rogers and friends Paul Champion and Jim Bellew moved to Tallahassee and opened a downstairs grotto club called the Baffled Knight. Those three, the Baffled Knights, were the house act.

Rogers’ brother and his manager both think the group’s name was autobiographical: an ironic epigram that lashes together Rogers’ deep idealism with the frustration engendered by his youthful search for purpose.

In 1966, although Rogers was a seasoned performer, fame continued to elude him. So he took what would ultimately be a pivotal trip to Massachusetts, where he planned to interview for a job with an architectural firm. Perhaps his father had persuaded him to give the family business one more try.

Jack speculates that his brother might well have taken the job, had it been offered. The frustrated folk-singer had come to believe that if architecture was his indeed his destiny, then at least he needed to establish an identity away from Florida, outside his father’s substantial shadow.

But it wasn’t to be. While in Massachusetts a friend persuaded Rogers to take a side trip to New York City and audition for a slot with the Serendipity Singers, a popular folk group that had reached the Top 10 with “Don’t Let the Rain Come Down (Crooked Little Man)” two years earlier .

Although the audition was unplanned, Rogers was hired to sing and play lead, acoustic and electric guitars. When his prowess as a storyteller became apparent, he became the group’s front man, introducing and setting the scene for their songs when they appeared on such television shows as The Tonight Show, The Ed Sullivan Show and Hootenany.

But while the instant fame offered Rogers a sense of validation, he felt unfulfilled and out of place. ‘’I was merely a hired gun, so to speak,’’ he told the Orlando Sentinel in 1987. ‘’I simply signed on with an already established group.’’

He left the Serendipity Singers after two years and began the grueling process of building a solo career, one concert at a time. He got bookings in Coconut Grove, where he moved. And he established something a circuit for himself, playing coffeehouses and clubs in St. Augustine, Gainesville and Tallahassee.

Finding that well-crafted acoustic songs weren’t always enough to hold a rowdy crowd’s attention, he honed his stage persona and his storytelling, which would later be described as a combination of Mark Twain and Will Rogers, if either humorist had been a Floridian.

By the early 1970s, Rogers was playing across the U.S. and Canada. In 1974, when he appeared at the Philadelphia Folk Festival, PBS taped his performance for nationwide broadcast. The following year, the network produced a television special, Gamble Rogers: Live at the Exit In, which originated in Nashville.

Indeed, Rogers’ literary bent and subversive approach to Southern humor seemed tailor-made for PBS. He was hired as a current events commentator on NPR’s All Things Considered in 1976 and 1977 and then again in the 1981 and 1982.

One of his monologues, “The Great Maitland Turkey Farm Massacre of 1953” was included in Susan Stamberg’s book Every Night at Five: The Best of all Things Considered.

Rogers also wrote two radio dramas, Good Causes: Confessions of a Troubadour, which aired in 1977, and Earplay, which aired in 1980. A Rogers-scripted television play, The Waterbearer, debuted in 1984 and was rebroadcast twice in 1985.

In the fall of that year, Rogers co-hosted and performed on AT&T Presents Carnegie Hall Tonight, which followed a concert appearance at Carnegie Hall with the legendary Doc Watson, a bluegrass icon and a childhood hero.

In part because of his PBS affiliation, Rogers was gaining a following among intellectuals, who appreciated his facility with language and his ability to satirize both rural ignorance and urban pretention in a pointed yet hilarious way.

Journalists were also among Rogers’ biggest fans, describing him as “an American treasure … an awesome talent … a rare and guaranteed treat … worthy of inclusion in the Smithsonian.”

What differentiated Rogers from dozens of would-be Woody Guthries? It had to be the stories. Rogers enlivened his tales of life in Oklawaha and Snipe’s Ford, the county seat, with the antics of a host of colorful characters, most notably “Agamemnon Abramowitz Jones,” “Downwind Dave” and “Sheriff Hutto Proudfoot.”

Snipes Ford, where “sorriness” was considered a prime virtue, had little of the precious charm of Lake Woebegone, Garrison Keillor’s frozen outpost of Lutheran virtue “where all the women are strong, all the men are good looking, and all the children are above average.”

In Snipes Ford, by contrast, the center of community activity was the Terminal Tavern, a scurrilous dive “where the ‘good ol’ girls put their earrings on with staple guns and the good ol’ boys know it’s always easier to get forgiveness than it is to get permission.”

Rogers once said, “The stories I tell are all true, except the few that are obviously whimsy. Each and every one of the characters in my stories started out representing a specific person. The characters may tend to be outlandish, but their statements resonate with a certain amount of horse sense.”


One weekend at Flagler Beach, Gamble and his wife, Nancy, returned to their campsite from a four-hour bike ride, tired and ready to go home. The October daylight was waning, heavy weather was coming in and the surf was head-high and dangerous.

The Halloween Storm, a three-hurricane hybrid that sank the swordfishing boat Andrea Gail and formed the basis for Sebastian Junger’s bestselling novel, The Perfect Storm, was only a few days away.

It was no day for swimming, but a tourist from Ontario, Canada, had gone into the water and gotten into trouble. His young daughter ran to Rogers, pleading for someone to help her father.

His arthritis, relentlessly worsening since childhood, had frozen his spine to the point where he could barely twist around enough to back up an automobile. In fact, he’d struggled in the calm waters of a swimming pool just weeks before.

Rogers had to know that he couldn’t maneuver in that surf on his own. Yet he stripped to his shirt and shorts, grabbed a plain air mattress from under a sleeping bag and started into the water.

As minutes ticked by, park ranger Chuck McIntire, a strong swimmer, joined Rogers and another would-be rescuer. McIntire swam past Rogers, who signaled that he was still all right.

As McIntire continued outward, working the undertow and searching for the Canadian, a big wave took Rogers’ air mattress away. The surf overcame him and he drowned at the age of 54.


St. Augustine resident Harvey Lopez describes how three of Gamble’s friends were enlisted to build his casket: “Nancy said, ‘I have a big favor to ask of you. I’d like for you to build a coffin for Gamble.’ What could I say? ‘No problem, when is the funeral?’”

Lopez called two friends, Jesse Allen and Brad Kinsey, who were boat builders, woodworkers and cabinetmakers: “We decided we were going to build it like a boat,” he says. “Found some old Florida cypress. We planed it out in planks, smoothed it and started putting it together. We stained it an old rosewood color, just like the ‘Rosewood Casket’ song.”

Since you can’t cross the River Styx in a boat without a paddle, the trio also crafted an oar and slipped it inside the coffin.

Tributes poured in from friends and fans. Buffett dedicated his Fruitcakes album to Rogers’ memory: “I dedicate this collection of songs to a troubadour and a friend who has gone over to the other side where the guardian angels dwell and has, in all likelihood, become one.”

The state Legislature honored Florida’s quasi-official musical ambassador by creating the Gamble Rogers Memorial State Recreation Area, a 144-acre park on Flagler Beach between the Atlantic Ocean and the Intracoastal Waterway.

St. Johns County opened Gamble Rogers Middle School near St. Augustine in 1994, and the Division of Cultural Affairs named Rogers to the Florida Artists Hall of Fame in 1998.

Gamble Rogers is buried in Winter Park’s Palm Cemetery, beneath a marble headstone that reads “Florida’s Troubadour.”

But his legacy lives on. Each May, a confederation of Rogers aficionados organize and stage the Gamble Rogers Festival, a St. Augustine hootenanny that commemorates his life and work and attracts performers whose style and personal history relate to Rogers’ own.

Yet, despite the popular show business cliché, not one of them so far has suggested that he is, or knows who will be, “the next Gamble Rogers.”

Gamble’s Guitar


Chicago-based folk-singer Michael Peter Smith, who is appearing at this year’s Gamble Rogers Festival, wrote a haunting and poignant song about his friend. Here’s a snippet:

Behind Spanish walls in Winter Park,
In the smell of jasmine in the dark,
Running a speed trap outside Starke,
I thought I heard Gamble’s guitar.

Whole lot of country, whole lot of blues,
Whole lot of sunshine, sand in your shoes,
Sound of a player who paid his dues,
Put some miles on that Mustang car.
Shot of Merle, jigger of Chet,
Little bit of Will McLean, I bet,
Only the wind in the palms and yet,
I thought I heard Gamble’s guitar.

Keepers of the Flame

GR-PaulaRosenCompilationofImages 007

The Gamble Rogers Memorial Foundation, based in Gainesville, was established by Rogers’ longtime manager, Charles Steadman, and others to preserve the folk-singer’s memory and his music. On the foundation’s website,, you can order his CDs, watch performance videos and read about his life. A guestbook allows fans to reconnect and share memories. The foundation also plans to produce a network-caliber video documentary and a 30-year retrospective CD compilation of Rogers’ songs.

Harold Fethe, a longtime friend of Gamble Rogers’, is a California-based entrepreneur and consultant who writes for a wide range of publications and performs as a jazz and rock guitarist. Randy Noles is publisher of Winter Park Magazine and author of two books on traditional American music.

Share This Post