The Pensacola Police Historic Society

Looking at the case of the Black Widow on Monday, January 6, 2025

“He’s a lucky man…God’s been with him.” Those were the words of Albert Gentry, brother of John Gentry. Albert was referring to John’s two close calls with dea1h. When John was serving in the military in the Vietnam War, he stepped on a mine while on patrol. The mine exploded under him causing severe injuries and a lengthy hospital stay, but no permanent injury. Then, on Wednesday night, June 25, 1983, John’s car exploded when he turned on the ignition in downtown Pensacola.

John Gentry owned a wallpaper retail company. In 1983, John met a woman named Judy Buenoano, a nurse who lived in the nearby town of Gulf Breeze. Despite her nursing qualifications, Judy owned and operated a nail sculpturing salon. She was a successful businesswoman from all appearances of her lifestyle.

Rick Steele was a native Pensacolian and a second-generation Pensacola Police Officer. His father, H.O. Steele, retired as a sergeant, as did Rick. After his retirement, Rick served with the Pensacola Airport Police and with Pensacola State College. When he retired, he was one of the oldest active police officers in Florida.

Ted Chamberlain was born on July 21, 1945, in the historic town of Attleboro, Mass. Both his grandfather and his father had been police officers, so Ted was destined to follow in their footsteps. Right out of high school, Ted joined the U. S. Army and was sent straight to Vietnam to fight in the war.  After he got out of the Army, he returned to Massachusetts and joined the “family business” of law enforcement, becoming an officer in his hometown. In 1976, Ted became a Pensacola Police Officer. Ted retired in 2013, ending his 37-year career. During that time, he served in patrol, the Tactical unit (his favorite), and Investigations. Ted was the kind of officer who very much liked working with the guys. An amateur race-car driver, he always drove with the windows down and one foot on the gas & the other on the brake. After Ted retired from the Pensacola Police Department, he was hired as a cold-case investigator for the Escambia County Sheriff’s Office.

After the explosion, it didn’t take long to figure it was caused by a criminal act. Someone had deliberately set a bomb in the car. In the middle of the night, the phones of Detectives Rick Steele and Ted Chamberlain rang. In a 2019 interview with Ted, he said that he first suspected Judy when he arrived at the scene. Ted recalled “Instead of parking near the restaurant, she parked her Corvette a long way off – why? After the initial incident, Ted interviewed Judy a few days later. Her arrogance bothered him. “She bragged that she earned $500,000 per year.” He later found out that the life insurance Judy took out on Gentry was for $500,000. One of the first crucial thing a detective does when assigned a case is to check the background of all the players. In the Police Department’s Records section, he searched for Judias Buenoano. Nothing. Ted had a sudden thought. A young Hispanic woman worked in the Records section, so Ted asked her “What does the name Buenoano mean in English?” “It means Goodyear” she answered. Bingo! He was introduced to several dea1h investigations that had been worked involving husbands, boyfriends and…her son. The locations ranged from Pensacola to Colorado, and insurance money was involved in every one of them. 

Detectives Steele and Chamberlain worked the case. As the case was looked into, it looked more and more like Judy had planned the whole thing. Further investigation revealed that Buenoano had previously tried to k1ll Gentry by using poison – this wasn’t the first time. In an attempt to improve his health, she began giving him a regimen of “Vitamin C” that would make him feel better and be healthier, she told him. A task force involving investigators from all interested agencies was formed. Soon, the task force members began suspecting Buenoano in the dea1h of her son, her husband, her common-law husband, and perhaps one or two more people. Each person had a life insurance policy paid to…Judy Buenoano.

When the details of the case hit the media, she was dubbed “The Black Widow,” which is the name usually given to most female serial k1llers.

After long, and exhausting trials, Buenoano was, on March 31, 1984, convicted of pre-meditated first-degree k1lling in the dea1h of her son, who drowned while on a canoe trip with Judy in the East River. She was also convicted of the attempted murder of John Gentry and received a 12-year prison sentence for it. Buenoano was convicted of premeditated First-Degree murder in the death of her husband, James Goodyear, in Orlando in 1971. Because of the work of Steele, Chamberlain, members of the task force, and State Attorney Russ Edgar, she received the dea1h penalty and met her fate on Monday, March 30, 1998.

Please join me at the next meeting of the Pensacola Police History Society on Monday, January 6, 2025, at 6:00 PM. I have invited Retired Officers Ted Chamberlain and Rick Steele as special guests. We meet at “The Mission” Anglican Church, 609 N. Alcaniz Street. Everyone is invited!

Mike Simmons