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Former Hillsborough County Sheriff Cal Henderson dies at 77

Henderson served as Hillsborough County Sheriff from 1992 to 2004.
Cal Henderson first won election as sheriff with the endorsement of his predecessor, Walter Heinrich.
Cal Henderson first won election as sheriff with the endorsement of his predecessor, Walter Heinrich. [ Times (2003) ]
Published Jul. 16
Updated Jul. 16

Former Hillsborough County Sheriff Cal Henderson, who over a nearly 40-year law enforcement career forged a reputation as a steady and well-liked leader, died Friday at the age of 77.

Henderson served as Hillsborough County Sheriff from 1992 to 2004. His law enforcement career began in 1965 with the Tampa Police Department. He joined the U.S. Border Patrol two years later, then served with the Central Intelligence Agency in South Vietnam, the Sheriff’s Office said in an announcement.

Henderson was hired by the Sheriff’s Office as a patrol deputy in 1969. He rose through the ranks, later serving as a major in each of the operational divisions of the Sheriff’s Office. In 1985, he was promoted to colonel of the Enforcement Operations Department.

A Democrat, Henderson had the endorsement of 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, David Gee, in 2004.

Former Hillsborough County Sheriff Cal Henderson has died at the age of 77, the sheriff’s office announced Friday afternoon.
Former Hillsborough County Sheriff Cal Henderson has died at the age of 77, the sheriff’s office announced Friday afternoon. [ Hillsborough County Sheriff's Office ]

“He was a great boss,” Gee said Friday. “He was one of those people, he’d correct you, but he always was careful. He followed that old adage that people will forget what you said, but they won’t forget how you said it. He always tried to be kind.”

Gee said Henderson will be remembered for his charity work that sparked efforts still in place today. Henderson once sat atop a platform over Dale Mabry Highway, vowing to stay 58 hours to raise money for the Special Olympics.

“Just one of the nicest people behind the scenes I ever met,” Gee said. “I always said he didn’t have a malicious bone in his body. We enjoyed working for him.”

HIllsborough Chief Judge Ron Ficarrotta, a former prosecutor, remembers seeing pictures from the 1970s of Henderson with long hair when he worked undercover.

Former Hillsborough County Sheriff, Cal Henderson, as an undercover narcotics deputy early in his career.
Former Hillsborough County Sheriff, Cal Henderson, as an undercover narcotics deputy early in his career. [ Courtesy of Cal Henderson ]

”He knew the operation from the street level up,” Ficarrotta said. ”He was an outstanding sheriff and a great partner to work with here at the courthouse.”

While Gee lauded Henderson for his compassion, he emphasized that his former boss wasn’t afraid to stand up for his officers when needed. That even included him disarming a man with a machete once, according to Gee.

“He’d get out there and roll his sleeves up,” Gee said. “He was a tough guy when he needed to be. You’d definitely want him in your corner.”

Gee said Henderson used to like to hunt and camp, and after he retired, traveled a lot with his wife.

Henderson is survived by his wife, Jeanne Henderson, who still lives in Hillsborough County; a daughter, Sheri Portalatin; two grandchildren, David and Vanessa Portalatin; and two sisters, Jackie Truesdell and Troy Taylor.

“Sheriff Cal Henderson was a remarkable man and selfless public servant for decades,” said current Hillsborough Sheriff Chad Chronister in a statement. “His legacy and contributions to our country, the Hillsborough County Sheriff’s Office, and the community he proudly served will never be forgotten.”

Hillsborough Sheriff Cal Henderson waves to passersby from the platform where he will stay for 58 hours as part of a fundraising effort for the Special Olympics. The platform was on Dale Mabry Highway just south of Waters Ave.
Hillsborough Sheriff Cal Henderson waves to passersby from the platform where he will stay for 58 hours as part of a fundraising effort for the Special Olympics. The platform was on Dale Mabry Highway just south of Waters Ave. [ GOETHE, THOMAS M. | St. Petersburg Times ]

Mark Ober, the Hillsborough State Attorney from 2001 to 2016, described Henderson as standing tall “beside the great sheriffs of Hillsborough County.

“He had a quiet strength that was contagious to those he worked with,” Ober said. ”Cal was, simply put, one of the good guys, and we owe him a debt of gratitude.”

Ober said Henderson well understood the differing roles of their respective offices.

”He was matter of fact, but he understood the difference between being the sheriff and the job that prosecutors had,” Ober said. “We would talk about the difference between probable cause and reasonable doubt, and he understood that.”

Ober said they had a great working relationship.

“He understood the powerful and essential role he played in the criminal justice system,” he said. ”I had many, many, many meetings with him and I never saw him rattled.”

Hillsborough County Sheriff Cal Henderson rushed to the scene where several of his people were injured at 78th and Causeway Blvd at a 7 Eleven store. A deputy at right is telling him what she knows of the incident.
Hillsborough County Sheriff Cal Henderson rushed to the scene where several of his people were injured at 78th and Causeway Blvd at a 7 Eleven store. A deputy at right is telling him what she knows of the incident. [ ROBERT BURKE | Tampa Bay Times ]