A 'true gentleman,' Henry Broadwell Watkins III remembered for success in business and life

Henry Broadwell Watkins III was anything but ordinary.

He led an extraordinary life. A life of fun, meaning and purpose.

Watkins, 72, died Nov. 13, after what his family describes as a "long and disturbing fight with a brain tumor."

He is remembered for his wisdom, his compassion and his generous heart – and as a true gentleman, who liked to sport popped collars in the day, and bow ties at night.

"He was an amazing guy and just a ton of fun – and a great dancer. He loved music too," said his youngest daughter, Anne Watkins Morrison.

She called him a "fixture" on the Naples social scene.

While he worked humbly behind the scenes, he's an important part of the Watkins family's legacy of hospitality in Naples.

With his knowledge of finance, Henry helped ensure the Naples Beach Hotel survived and thrived until it came time to sell the property after more than 70 years in business. He played a pivotal role in the sale of the 125-acre property to a developer that's promised to keep the family's traditions alive, including the former hotel's beloved HB's restaurant and Sunset Beach Bar, preserving their strong community connections.

The former beachfront hotel, off Gulf Shore Boulevard North, will be replaced by a five-star resort and ultra luxury residences, going under the name Naples Beach Club and operating under the iconic Four Seasons brand, marking its debut on Florida’s Gulf Coast.

Jay Newman, chief operating officer for The Athens Groups, the project's developer, said he's deeply saddened by Henry's death.

"With Thanksgiving just around the corner, I am thankful and honored to have known Henry as a friend," he said.

In an obituary shared with the Daily News, Henry's family said he felt a "huge responsibility" to continue the legacy of his grandfather, who shared his name and had a "remarkable" vision to improve the city when he purchased the Naples Beach Hotel and golf course in the 1940s.

Henry III wanted to keep Naples special, while making sure it kept up with the times.

The hotel was but one part of his life.

From our archives: Plans unveiled to tear down Naples Beach Hotel, redevelop resort, add condo towers

More: It's official: Iconic Naples Beach Hotel property changes hands, redevelopment to begin

An accomplished financier

Before returning to Naples in 1992 to be closer to his brother Michael and the hotel they co-owned, he built a career as a successful financier, which began right out of college in New York City at the old Manufacturers Hanover Bank, where he spearheaded funding for such important projects as the Alaskan oil pipeline, according to his family.

In the 1980s, he moved on to the Wells Fargo Leasing Co., where he financed hundreds of barges for transporting goods on the Mississippi River and the modernization of Motel 6, which put TVs in rooms nationwide.

From there, he landed at CitiBank, where he became a top performer. His proudest accomplishment: Financing a major road project in Ankara, Turkey.

"He accomplished such amazing, different things, which a lot of people don't know. My dad made it a very strong point that he wanted to go out on his own, to accomplish his own success, and he did," Morrison said.

She described him as brilliant and as inspiring to her and her older sister. He had an entrepreneurial and philanthropic spirit.

After moving back to Naples, Henry helped establish Founders National Trust Bank and later started the Naples Management & Investment Co. He built a tech company from "infancy to a multimillion-dollar company," according to the obituary.

He helped found the Pelican Bay Business Association and form Partners in Education, now known as Champions for Learning, to support local schools. He served on the boards of many local nonprofits, including Youth Haven and the YMCA. He was named one of the 100 Most Influential Business Leaders in Naples.

A lover of life

His family remembers Henry's love for "sunsets, traveling, problem solving, negotiating and a memorable dinner" – and life in general.

He had many passions, including sports.

"He had a huge love for baseball," Morrison said. "He only played for a little bit, but he loved the Pittsburgh Pirates."

For years, no matter the theme of the annual Great Dock Canoe Race in Naples, he and his brother Michael, who managed the Naples Beach Hotel's day-to-day operations for decades as its president, would wear their Pittsburgh Pirates uniforms.

Even as a young kid, Henry loved the team. He built a radio with his father, so he could listen to the commentary for the team's games and keep track of their scores, Morrison recounted.

He passed on his love of sports.

At the age of 7, Morrison took up tennis, then became a competitive player within a few years, eventually earning a college scholarship for it. She cherished the many road trips she and her dad took together for games she played across the state, sometimes traveling late at night to get where she needed to go in time.

"He was always so great because he was always there for me to help me with that. It was something very special," she said.

On the road trips, he loved to listen and sing along to the "oldies" on the radio, which she learned to love and appreciate, although at the time she may not have realized it.

After learning of her father's death, many of the friends she met through tennis reached out to offer their sympathy and express their sadness. He used to crunch statistics for any player who asked about their odds of winning a match, as he did for her, back in the day, she said.

"He made it a math equation for himself. Each time. It was unreal," she recalled.

More than that he always showed compassion and caring toward her friends, and everyone else.

"He felt so hard. He would cry at a sad movie," she said.

Henry also passed along his spirit of entrepreneurship. Both of his daughters started businesses of their own.

His oldest daughter Devon Watkins Holden said there was so much to love about her dad.

"He was an amazing cook and we loved laughing in the kitchen and bumping elbows," she said. "His Yorkshire pudding was his specialty for Christmas."

She appreciated that he always stood by her side, even when she made mistakes.

"And, boy did I make mistakes," she admitted.

After growing up and leaving Naples, Holden said she always looked forward to coming back home.

"I loved when he would pick me up from the airport and when we got to Broad Avenue, we would open the windows and smell Naples," she said.

She'll miss that, along with the laughs, the music and her dad's calming voice.

A true love story

In the obituary, the family shared that Henry and his wife Bernadette "stayed side by side until the end," and described their relationship as a "true love story."

"She's heartbroken," Morrison said of her mother.

The relationship between her mom and dad truly represented the virtue of "until death do us part," she said.

Henry and Bernadette were married for 45 years. They were set up by a close friend of her parents, with connections to his family.

"I kept saying I never wanted to get married. Then we went on from that first date," she said.

When they first met in New York, she had a career in fashion and he in finance, which kept them super busy, but they always made time for special dinners together, which included visits to some of the city's finest and most famous restaurants.

At home, she always dressed the table up for dinner, with sophistication and style.

"He so appreciated it," she said. "His first grandmother was like that."

When they lived in New York, they enjoyed Broadway shows and dancing. The dancing continued throughout their lives together.

"We loved to dance," she said. "He was a beautiful, romantic dancer. We were just romanticized by dancing."

In her heart, no one could ever take his place.

"I'll never marry again," she said. "He'll always be the love of my life."

Henry had an undeniable affinity for Naples, as his hometown.

After attending Lake Park Elementary and Gulfview Middle School in Naples, he went on to graduate from the St. Andrew's boarding school in Boca Raton.

Following in the footsteps of his grandfather and great grandfather, he attended Hamilton College in New York, where he earned a bachelor of science degree, with a major in mathematics.

Decades ago, retired Collier County Sheriff Don Hunter, who knew Henry as "Hank," recalls playing Little League baseball with him and having what are now known as 'playdates' with him and his brother. He said their dad, Henry B. Watkins, Jr., coached the team, which won a regional championship.

"He was a happy and always smiling pal," Hunter said of his childhood friend.

Beyond his good humor and many friends, the youngest Henry's most striking attribute was his "outstanding freckles," he said.

Henry was deeply devoted to his church Trinity-by-the-Cove in Naples, which he'd attended since childhood. He wasn't just a familiar face, but a familiar voice in the pews.

"Everybody knew when my father was in church," Morrison said. "He loved to sing the hymns, and he knew every hymn, and every word."

His mother Mary played the organ at the church for generations, sparking his love for music and God.

A memorial service will be planned at a later date.

This article originally appeared on Naples Daily News: Harry Watkins III, a former owner of the Naples Beach Hotel, has died.