Former sheriff Cal Henderson remembered for his humor, love of Hillsborough

RIVERVIEW — Family, friends and fellow public servants remembered former Hillsborough County sheriff Cal Henderson as a man who always came back home, bound by duty and love to watch over a community that nurtured him and his family.

With help from country songs by Patty Loveless, Jo Dee Messina and Jamey Johnson, the tears that flowed — as well as heavy summer rains — soon gave way to sunshine and smiles during a celebration of life ceremony Wednesday at The Regent event center in Riverview.

Henderson, who served more than four decades as a lawman, died July 16. He was 77.

Born in Tampa, Henderson was given the name Homer Caddell Henderson Jr., his sister-in-law Tammy Bracewell told the gathering.

“He coined Cal with his buddies when he was a teenager because he couldn’t imagine having to go through life as ‘Homer,’” she said.

In this and other challenges, big or small, Henderson could always find an answer, friends and family said.

Blessed with charm and good humor, Henderson was remembered as a quiet man with a dazzling, crooked smile who knew to trust his gut in even the toughest situations. He knew how to laugh at himself and at the absurdity of life but also felt a responsibility to protect and care for others.

“He was a true gentleman who attracted friends in an instant and kept them for a lifetime,” said friend Michael Thatcher, former director of the Shriners Order of Jesters Tampa Court 89. “He was in his element when there was a job to do or a challenge to be met. He lived a life of service.”

In one final act of service, Bracewell said, Henderson arranged to have his brain donated for research to the University of Florida medical school.

On display during the memorial were awards and commendations as well as headlines from memorable crimes during Henderson’s time as sheriff, among them, “Sheriff reaps marijuana crop,” and, the time he led a raid on a “topless female wrestling exhibition.”

Henderson was president of the Florida Sheriff’s Association and served on the boards of the Shriner’s Children’s Hospital and the Florida Special Olympics. As Sheriff’s Association president, he helped author and implement a number of state laws credited with ushering in two decades of decline in violent crime.

Henderson began his life of service by enlisting in the U.S. Army in 1961. He joined the Tampa Police Department in 1965. Two years later, he signed up as a U.S. Border Patrol agent and later joined the Central Intelligence Agency, serving in South Vietnam.

Henderson returned in 1969 when he was hired by the Hillsborough County Sheriff’s Office as a patrol deputy. He quickly rose through the ranks, serving as major in each operational division before he was sworn in as colonel of the Enforcement Operations Department in 1985.

That’s the job title Henderson had when he first met Chad Chronister, the current Hillsborough sheriff. Chronister had just completed his training to become a sheriff’s deputy, and, eager to make a good impression on his new boss, volunteered to help in his first campaign for election.

The young deputy’s first job with the campaign was to post “Vote Henderson” signs outside the old Tampa Stadium at Hillsborough Avenue and Dale Mabry Highway.

Chronister described the episode in an interview after the memorial.

“So this was the very first assignment he ever gave me. I’m just happy to be there and happy to be part of the group,” he said.

“I grab my first campaign sign, stick it in the ground and then, ‘Boom!’ It went straight into a water main and it was like a geyser just shooting water into the sky. I thought, ‘This guy’s going to fire me before I even get started.’”

He didn’t. Instead, Henderson called him at home later that evening.

“He just told me, ‘Listen, I appreciate you being out there. Don’t worry about it. We’ll get it fixed. Everything can be fixed.”

Henderson showed compassion at every turn, whether to a bumbling deputy or a homeless man on the street, Chronister said — a quality the new sheriff has tried to emulate.

A Democrat, Henderson had the endorsement of incumbent Sheriff Walter Heinrich when he first was elected in 1992. He was re-elected without opposition in 1996 and faced only a write-in challenge in 2000. He didn’t seek a fourth term and was followed by his hand-picked successor, Republican David Gee, in 2004.

Gee retired in 2017, less than a year into his fourth four-year term, and recommended that the governor appoint Republican Chronsiter to replace him.

Henderson was the 28th sheriff of Hillsborough County and worked 35 years with the Sheriff’s Office.

He served three four-year terms as sheriff before retiring to spend time traveling the world with his wife of 38 years, Jeanne. He loved camping and hunting and spending time with his fellow Shriners, as well as laughing with his brother and sisters — Larry Henderson, Jackie Truesdell and Troy Taylor — doting on daughter Sheri Portalatin, spending time with grandchildren David and Vanessa Portalatin, and playing with his dogs.

He was a man in love, Bracewell said — in love with his job, his family, his community and the little things in life that make you laugh. He never seemed angry, despite all the responsibilities and headaches of his job, and he never looked stressed. Even as he battled prostate cancer and the nerve disorder Bell’s Palsy, Henderson was easygoing, even keel and friendly, with a sense of humor that bordered on goofy.

In recent days, he was afflicted with Alzheimer’s disease and was moved to an assisted living facility. Near the end, it was hard to understand what he was saying, Bracewell said, but his sense of humor endured.

“I couldn’t understand the last story Cal ever told me, but it was a good one,” she said. “The only thing I could make out was that it ended with him saying, ‘He’s crazier than an outhouse rat,’ and laughing away at his own joke.”