Quiet Power: The Story of the Watkins Family in Naples

How three generations of the Watkins family have helped build the Naples of today—bringing forth Cambier Park, The Naples Players and other local icons.

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The Watkins name is kind of synonymous with The Naples Beach Hotel & Golf Club, but its guests may not pick up on that at first. Taking a closer look, though, they might discover how much the family is ingrained in the hotel, as well as the community that surrounds the sprawling waterfront resort.

Remnants of Old Naples decorate the hotel. Imagery of the Everglades graces the walls in paintings from Paul Arsenault or photos by Clyde Butcher. The Seminole Store and the Beach Store in the lobby are named after old haunts on Third Street downtown. The hotel’s restaurants—the fine-dining Broadwell’s and beach spot HB’s on the Gulf—are named after Henry Broadwell Watkins Sr., the man who grew the hotel and the community around it.

“We try to capture some of the good of Old Naples,” says his grandson and hotel president Michael Watkins.

Michael is fastidious about the resort, picking up scraps of trash as he walks the grounds, walkie-talkie in one hand to radio in any repairs he spots. Tall and lean with reddish hair like his grandfather’s, he’s soft-spoken yet amiable, nodding his head and exchanging pleasantries with guests as he passes. The Watkins family since the times of Henry Sr. have had the same sensibility—in tune with the community without demanding attention. “We’re not fancy,” Michael says. In fact, his mother, Mary—slight and unassuming like her son—still lives in the modest seaside home in which she and her husband, Henry Jr., raised Michael and his brother, Henry III.

Old Naples is still around, but you have to look beyond the high-rises and mansions to the cottages shrouded with native flora downtown, like Mary’s ranch house. The look reflects the Naples of the 1940s that Henry Watkins Sr. came across when he was looking for a new challenge in life. The Watkins name doesn’t decorate too many buildings, but the family played a key role in the development of the community. Cambier and Lowdermilk parks both have Watkins fingerprints, along with NCH and The Naples Players. Actually, it’s hard to walk around downtown and not see the Watkins influence.

The family is an “anchor of the community,” says local historian Lois Bolin. “They could have done anything (with their property), but they have a love for the community, a love of heritage.”

Mr. Watkins Goes to Naples

Naples was a second life for Henry Watkins Sr. His first was spent as a toy maker. He was a shareholder and executive in Kilgore Manufacturing in Westerville, Ohio, once the world’s largest manufacturer of toy cap pistols. He retired wealthy at age 54.

Family members describe him as reserved but still very much a people person. “He always had friends around,” says his son Henry Watkins III. He was a serious businessman with a competitive streak that carried over into other areas of life. All of the Watkins men liked sports—from baseball to tennis to fishing. The patriarch still played golf well into his 80s. “He didn’t like to lose; he didn’t like to hit a bad shot. But as he got older, his level of expectations lowered,” says Henry Watkins III.

His daughter-in-law Mary Watkins remembers him as a visionary, seeing the big picture of what Naples could become. “Who would have thought to invest in a hotel that you could only get to by a two-lane dirt road?” she asks.

Watkins and his family used to winter on Fort Myers Beach. He stumbled across Naples when looking for lodging once. Back then, the Naples Hotel, built in the 1880s, was two blocks from the Naples Pier (and not to be confused with the The Naples Beach Hotel, which is a separate complex). Family aren’t quite certain why he decided to uproot and start a new life at age 54, but Watkins gathered a couple of his friends and bought it in 1946. With the sale came 90 percent of the land in Naples (which at the time was about 2,200 acres), along with the 18-hole golf course and club. With his partners, he formed The Naples Company.

The group was the last to essentially “own” Naples, controlling the land and, in large part, the future. It was a key moment. They could have maximized their profit, packing in homes and hotels. But they didn’t want to do that. Yes, it was a business venture. But Watkins wanted something more. It was a chance to shape a community.

Not everyone knew that. Naples, A Second Paradise, an exhaustive history of the city by Lila Zuck in conjunction with the Naples Historical Society, recounts much handwringing over what the newcomers wanted. Naples Company Executive Darold Greek once said, “We were deluged with requests to come to cocktail parties so the local people could ply us with questions. I can assure you they didn’t want it to be another village with hot dog signs and alligator wrestling signs … and high-rises on the beach.”

Old Naples

When Watkins came to Naples, the town was still pretty secluded. But a community was forming. It was a laid-back vacation spot—popular with hunters and fishermen. The center of town was the Four Corners—the intersection of Fifth Avenue and Route 41—which featured a few small shops, a service station and Ed Frank’s garage (of Goodlette-Frank Road fame) lining the dusty roads. Only about 1,200 lived there full time, creating the small-town feel. No one locked their doors. The preferred contract was a handshake. “There was an intrinsic trust in the community,” says Naples Historical Society President and CEO Elaine Reed.

Shortly after Watkins arrived, the Naples Company started shaping the town. They developed a few lots of houses, fixed up the old Naples Hotel, renovated some of their buildings, and rented space to clothing and jewelry owners. Watkins purchased the beach apartments that he later turned into the original building of what is now The Naples Beach Hotel.

Watkins was also thinking big-picture. He hired a consultant to develop the “Naples Image,” a planning document for the company’s land that forbid high-rises or other hotels on the beach, according to Zuck’s book. Another rule: Its buildings would not overshadow the environment. He worked with the town on the Naples Plan, an effort to help bring along development, such as paving roads and building sidewalks. One of the first major steps was establishing a park. The Naples Company donated about 11 acres that became Cambier Park.

The idea was that Naples could be a small town with big-city amenities, Mary recalls. In the ’40s and ’50s, Watkins and The Naples Company continued to push that ideal. The company donated two lots that later became Naples Memorial Hospital, swapped land with the town to start Lowdermilk Park and helped in the development of Coquina Sands, River Park and several churches. By 1958, Henry Sr. was largely out of the real estate business to shift more of his focus to the hotel. That same year, as quoted in Zuck’s history, a travel writer in the Miami Daily News wrote, “Wise and rigidly enforced zoning regulations, as well as remarkable community spirit, have protected Naples from the pitfalls into which some Florida resort communities have fallen.”

An old postcard of The Naples Beach Hotel & Golf Club

The Second Generation Arrives

Shortly after Henry Sr. moved, his son and daughter-in-law decided to join him. Mary met Henry Watkins Jr. when she was attending The Ohio State University for graduate work. Mary and Henry Jr. were married in September 1949. They moved in December. She had never been to Florida before.

She remembers those first months as lonesome. There were only about 1,500 people in town at that time. Mary recalls her first Christmas making eggnog from scratch for a party that evening. Her mother called and she fell into tears, a case of homesickness.

It was still an isolated community at the time with many transplants—people starting a new life to a degree. Eventually, bonds formed.

“Everyone knew everyone. Age didn’t matter. No one asked,” Mary recalled in one installment of the historical society’s video series Naples Oral Histories: If These Walls Could Talk!

When the husbands would go to work and the kids to school, Mary found she and her fellow wives were bored. So, she’d call someone up to go for a walk or to get lunch. Sometimes, they’d go shelling in the early morning, collecting the conches and others that are now hard to come by. They’d go to Third Street South to the soda fountain to get the best grilled cheese in town. Or, in the evening, they’d take in a movie at the theater next door, where the rain would make a racket on the tin roof.

Largely, small-town life was pretty tame. But the Watkinses were typically at the center of the entertaining. For fun, they once organized a scavenger hunt that’d take friends from the Pier to the cemetery to Keewaydin and by Omar Clark’s bar (between Fifth and Fourth avenues with a declaration painted on the outside wall that read, “Don’t Drink! But if you do, buy it here.”). It ended at the beach outside the Watkins house.

“We didn’t have much nightlife. You had to create your own entertainment,” Mary says.

The Watkinses attended Trinity-by-the-Cove church, and Mary played the organ, something she still does today. She joined the Naples Women’s Club when she first came over and was the first president of the Naples Junior Woman’s Club. One night, a theater director from Cape Cod was having drinks at Mary and Henry Jr.’s home. Discussion turned to the budding Naples cultural scene—live theater could work well here, they thought. The woman’s club helped fund a production of I Remember Mama in 1953. The show ran one night to a standing-room-only crowd at Naples High School (now Gulfview Middle). Eventually, that troupe became The Naples Players, which still performs.

The Watkins hotels housed concerts and fundraisers in their ballrooms. The annual Sandeater Golf tournament was held annually at the golf course. Everyone could play, and names were drawn from a Brandy shifter—didn’t matter your experience; you played with whomever you were paired. Mary always felt sorry for whoever got her name.

Henry Sr. installed a sense in his resorts that they were more than just a place to stay—they should be a second home for residents and guests. Retired coal and railroad executive Cooper Wood spent his winters there for at least 30 years, according to Zuck’s history. Hotel staff prepared his room with the same furniture each year. He spent his time whittling pelicans from driftwood he collected on the beach. He gave the small statues to close friends in Naples. “We got quite a few,” Mary says.

Naples Grows Up

The Watkins boys, Michael and Henry III, remember growing up in a community that still had a close-knit feel. They’d ride bikes from their beachfront home to Cambier Park, barely seeing a car along the way.

Changes slowly then suddenly came to Naples. In 1960, Naples had a population of about 4,500. Ten years later, it was 12,000. The reason in part was Hurricane Donna in late 1960. For 11 hours, wind and rain thrashed Southwest Florida, including The Naples Beach Hotel, which was reduced to a state that required a $1.1 million restoration. But what resulted ended up being a boon. Insurance companies and FEMA saw the area as primed for growth, so money started to flow in, making the area more attractive than ever.

The Beach Hotel continued to expand, the last guest room building finished in 1971.The old hotel was demolished, its business shifting to the Beach Hotel. The beach hotel remained a center of community activity, the Watkins family at the heart of it all. Michael and Henry III remember parties at the hotel and the house, including a July 4 bash to watch the fireworks attended by everyone from their school friends to Mary’s bridge club to Henry Jr.’s business associates. “(Henry Jr.) was very active. But he still made a lot of time for his family,” Henry III says.

Henry Jr. coached his boys’ Little League teams. He filmed the Naples High School football games, getting great joy if one of its players got a college scholarship based on his footage, Mary says. His community spirit was as strong as his father’s. He sat on a multitude of boards and commissions, including school, county commissioners and chamber of commerce. Henry Jr. initially started in real estate but got more involved in the hotel as his father shifted into retirement. In 1981, Henry Sr. died.

Naples got fancier in the 1980s, Michael Watkins remembers. The Ritz-Carlton and Registry Resort & Club (now the Naples Grande Beach Resort) opened, bringing upscale interest and more New Yorkers and Bostonians. Michael Watkins viewed the competition in a “rising tide lifts all boats” mentality in that the new hotels gave the area more national prominence and allowed the beach hotel to position itself as a less costly option. “It ended up helping us a lot,” he says.

The Third Generation

Michael always knew he wanted to run the family business. He started helping at the tennis courts as a teenager, then worked his way up. He got a graduate degree in hotel administration from Cornell University and, after working at another Florida resort, returned to Naples. He became president when Henry Jr. died in 1989.

Both he and his brother have become as ingrained and respected in the community as their parents. Michael’s wife, Ellin Goetz, is a well-known landscape architect, designing the grounds of Naples Botanical Garden, the Edison & Ford Winter Estates and The von Liebig Art Center, among others. Much of the family’s philanthropy has focused on education. Champions For Learning, the education foundation of Collier County, awarded the Watkins family its 2014 Heart of the Apple Award. This came after decades of the hotel hosting proms, teacher events and senior skip days (which Henry Sr. introduced to Naples), not to mention endless donations of time and money to the schools.

One of the lasting traditions at the hotel is the SummerJazz on the Gulf series. For the past 30 years, guests and residents have lined chairs on the hotel’s nicely manicured lawn to listen to jazz combos. Of the five beach hotels, Michael likes to think his is the most social.

“We just want to do nice things for the community. It’s difficult because the community has gotten so big. We try,” he says.

The community has changed; it’s no longer the village where everyone knows everyone else. The high-rises the Old Neapolitans loathed now dot the skyline. The Watkins family remains polite when asked about the growth, most of which has come outside Naples proper.

Mary chooses her words carefully when contemplating the question. She’s spent a lot of time in her golden years working with the historical society to preserve the past, from helping identify people in old photographs to fighting to preserve historic homes. From her lanai she can gaze out onto the beach that once hosted community cookouts and church baptisms. Neither of those happen anymore. Barbecues are outlawed on the beach. And the baptisms drew too many gawking tourists for the church’s comfort.

“People ask if this is what we expected. It isn’t,” Mary says. “But who would have thought?”

Henry III returned to Naples in 1992. He didn’t have much interest in running the hotel and made his name in banking in New York City. His financial background was needed locally in the wake of their father’s passing. He started a firm to manage the family investments locally. He and his brother both own the hotel and his investment firm—a 50-50 split. Between the two of them, they have five children. All live out of town. Their fathers are uncertain if they’ll return one day. “Time will tell,” Michael says.

No matter what happens, Henry III hopes one day generations will look back on the family and think of them kindly—that they were giving, that they cared about their hometown.

“If that happens, that would make me very happy,” he says.